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Find Places to Stay in Shelter Island Heights on Airbnb

Find Places to Stay in Shelter Island Heights on Airbnb

Discover entire homes and private rooms perfect for any trip.

Places to stay in Shelter Island Heights

Places to stay in Shelter Island Heights
Stunning, light-filled 1850s Victorian Farmhouse, perfectly located in Greenport Village. Featuring a large wrap-around porch, it is just steps away from the town's best restaurants, cafes and bars, and 3 blocks to the beach.
Just minutes away from the center of Greenport Village, The Farmhouse is the ideal place to escape and enjoy the beauty of the North Fork. This 4000sf + house features five jumbo sized bedrooms, three renovated bathrooms, fully-equipped and open, chef's kitchen, dining room, a gorgeous turn of the century fireplace and a generous private outdoor space with BBQ facilities to accommodate large groups. Large, oversized windows and plenty of original details have been wonderfully preserved in this historic Farmhouse. The house is in close proximity to all the great restaurants and bars on the North Fork, including North Fork Table & Inn, Noah's, Bruce and Sons, Little Creek Oyster Farm, First and South, The North Fork Shack, Love Lane Kitchen, and Case's Place. The house is a few blocks away from Aldo's for coffee, and the IGA Supermarket. Walk to 5th Street beach. Several other beaches including 67 Steps Beach and Town Beach are less than a 10 minute drive away from the house. All the great wineries that the North Fork is known for including Macari, Shinn Estate Vineyard, Clovis Point, Pellegrini, Kontokosta Winery, Bedell and Pindar are just minutes away. Walk to Greenport Harbor Brewery - a must!
Everything is walking distance, the Jitney and LIRR stops a short walk away. Close proximity to great beaches, wineries and restaurants including North Fork Table & Inn, Noah's, Bruce and Sons, Little Creek Oyster Farm, and The North Fork Shack.
  • Carlos & Nicole's home in Greenport was the best Airbnb stay I have to date. Carlos & Nicole themselves were warm, communicative, and responsive. The house itself was immaculate and had a very cool vibe and decor - we loved eveything down to our pictures :) If you're looking for an awesome place to stay on the North Fork, look no further. This place has location, style, and every amenity you may need (and even some you may not have though of - including kids' toys!).

    Elizabeth2020-03-08T00:00:00Z
  • Went for a weekday staycation to Greenport and we had such a wonderful time. It was so nice to stay in the house and play games and just have fun. !

    Victoria2020-02-20T00:00:00Z
  • This house is so beautiful and so perfectly located. It one the best houses I’ve stayed at on Airbnb. It came equipped with everything you’d need and plenty space for large group socialise within. I’d recommend this anyone who’s thinking of booking! A Absolute dream!!!

    Rebecca2020-02-09T00:00:00Z
  • This is the third year in a row that we stay in this house and we love it so much. The house is super clean, incredibly comfortable, and greatly decorated. If you’re looking for a place to stay with a group this is a great place!

    Brigeth2020-02-02T00:00:00Z
  • We had a lovely time staying at Carlos and Nicole's home in Greenport! I stayed with seven other friends over a weekend and perfectly fit our needs-- it's big and spacious, comfortable, beautiful, and convenient. It's nice how close it is to town, but also not in a noisy area. Carlos and Nicole themselves were very thorough and prompt in their communication, which I appreciated. We stayed during an extra cold weekend in January. Some of the rooms were a bit drafty upstairs, but part of that may have been related to a minor heating issue in one of the areas, which Carlos and Nicole said they would look into. I trust their follow through on this given their responsiveness throughout the process. Overall, I would highly recommend to anyone with a group. We hope to return one day!

    Molly2020-01-19T00:00:00Z
  • Loved staying at this Airbnb. It’s really gorgeous and so so comfortable — rooms are extremely spacious, beds are so comfortable, and the living spaces are perfect. My family and I had the best time here; it really felt like home. Would be thrilled to go back!

    Mary Jane2019-12-27T00:00:00Z
  • The Farmhouse was an excellent place to spend our girls weekend. The whole house is beautiful and in a great location - walking distance to Greenport village. Carlos and Nicole were so accommodating easy to get in touch with. They even let us have an early check-in. You can 100% show up with just your suitcase because everything you could possibly need is provided. They even had a welcome bottle of wine for us. We would totally stay here again!

    Caitlin2019-12-15T00:00:00Z
  • We had the best stay at the farmhouse ! We hosted our annual friends thanksgiving at this fine house and there was plenty of room for everyone to roam free and mingle. It was cozy, stylish, clean and welcoming. None of us wanted to leave! Carlos and Nicole were wonderful hosts. We have found our home away from home and will absolutely return ! Don’t think twice, just book it!

    Casey2019-12-08T00:00:00Z
  • Room Type

    Entire home/apt


    Property Type

    House


    Accommodates

    14


    Bedrooms

    5

    Greenport, NY, United States

    This beautiful, brand-new private suite with its private entrance is part of our contemporary home in Greenport Village. With its huge outdoor space and easy walk to the beach, your getaway is also just a few blocks from downtown Greenport's unique mix of cute boutiques, great restaurants and peaceful harbor life. The area's celebrated wineries are a short drive or bike ride away. See why Forbes Magazine recently named Greenport one of the 11 prettiest towns and villages in the United States!
    Your private suite with its own private entrance is part of a designer home in the heart of Greenport Village. Your personal area of the house is completely private, and includes a comfortable bedroom, a brand new bathroom with a gorgeous shower, a spacious entryway, plus a separate coded entrance to come and go as you please. **Read the check-in instructions to avoid walking through our front door.** ;) The guest suite also features a Keurig coffee machine for that first cup of the day, a kettle if you're a tea-drinker, plus a mini fridge to keep your rosé suitably chilled. Freshly-laundered towels, clean linens and toilet paper are also provided. You will also have use of wifi, an iron and a hairdryer.
    Our neighborhood in Greenport Village is quiet and leafy, while being just blocks from the water and all of the amenities downtown Greenport has to offer. The town boasts a vibrant mixture of harbor life, cute gift shops and excellent restaurants, as well as nearby wineries and beaches.
  • Perfect location in Greeport, Hillary knows all the best spots in the aera, and the place was super clean, nice and cozy even in the winter;).

    Jon2020-02-24T00:00:00Z
  • What a gem! An easy walk from the train station and ferry and the delights of Main and Front Street, this quiet, stylish, well-appointed space was everything we could have needed. I want to come back to experience it in summer but even in winter there was plenty to enjoy in town and the restful, small town atmosphere of Greenport is so charming. This was a perfect base for exploring and relaxing as well.

    Nora2020-02-17T00:00:00Z
  • Highly recommend. Clean, thoughtfully appointed place, perfect for a serene getaway. Excellent location. Hillary’s a terrific host -- considerate and responsive. Wish I’d been able to stay longer.

    Inge2020-02-08T00:00:00Z
  • Such a lovely stay! Right near the beach and downtown, a quiet, beautiful home.

    Tara2020-01-26T00:00:00Z
  • Hillary's place was clean and had the right amount of space for two people. It is a few blocks from the LIRR/Jitney station and about a 5 minute walk into town. Hillary was a super responsive and helpful host, and I would recommend her place to anyone interested in seeing Greenport!

    Sarah2020-01-20T00:00:00Z
  • We had a great time at Hillary’s!

    Akshay2020-01-01T00:00:00Z
  • The space was clean and cute! Hillary was a quick communicator and Greenport is a wonderful town!

    Erin2019-12-30T00:00:00Z
  • Hillary was a wonderful, friendly host. Check in was a breeze thanks to her detailed instructions. Her place was cute and clean, and had everything we needed for a great stay. The location was perfect - close to town and wineries. We can’t wait to return!

    Lauren2019-11-26T00:00:00Z
  • Room Type

    Entire home/apt


    Property Type

    Guest suite


    Accommodates

    2


    Bedrooms

    1

    Greenport, NY, United States

    The Case-Jennings House is a beautiful Shelter Island gem. "Anna's Cottage" was built in 1847 and stands proudly as one of the island's oldest homes. In the same family for four generations, this two-bedroom treasure was newly renovated and restored in 2017. It is dressed in contemporary farmhouse decor and located within one mile of restaurants, shops, the beach, ferry and a golf course. This immaculate and comfortable space is ready to welcome you to the simpler way of Shelter Island life.
    The Case-Jennings house is a two-family dwelling on West Neck Road cozily nestled next to the island's deli, signature gift shop and a stone's throw from the island's most popular beach, Crescent (Louis') Beach. Anna's Cottage (1,200 square feet) is an entirely separate (adjoining) house with private yard and private entrance. The house is 173 years old, please handle with care and respect the neighbor. There is a propane "wood burning" stove in the living room for those chiller nights. The stove is turned off in the Summer and warm weather. We keep this dwelling safe and clean. This is a two- story space and we provide a second floor fire ladder for safety.
    Beach permits are required for access to the town beaches and are available for purchase at the Shelter Island Town Hall (they can be purchased in advance). (We do provide the beach towels, chairs (with carrying straps) and an umbrella though)!
  • We thoroughly enjoyed our stay at this historic house. Florence goes above and beyond to make sure you have a pleasant stay.

    Jeffrey2020-02-16T00:00:00Z
  • Anna’s Cottage is a true gem and highly recommended for a trip to Shelter Island. We found the place impeccably clean on arrival, with Florence’s thoughtful touches to brighten all the rooms. A butane fireplace to warm you to the core in winter. We loved this listing so much, we are already considering a return trip in summer! The kitchen is stocked with utensils, pots, pans, and other necessities for cooking/ baking. Bring your own oil, spices & groceries. The deli next door keeps a lot of essentials, so no stress if you forget something. The local IGA (grocery store) is not far by car. Florence also provided helpful suggestions for places to eat around the island. We made some beautiful memories on this trip and it’s thanks to Florence ... for making it so easy for us to relax at Anna’s Cottage! Island Tip: We did a few trails around Shelter island and loved the winter landscape and beaches, especially the Green trail at the Mashomack Preserve.

    Milu2020-01-20T00:00:00Z
  • Florences place was perfect for a get away from the city. Great location on the island and super comfortable beds made for a good nights sleep.

    Gerard2020-01-02T00:00:00Z
  • Immaculate with all the right touches. Great location. Walk to beach, golf course, gift shop, deli. A beautiful home with every comfort. Can’t wait to return!

    Melanie2019-12-26T00:00:00Z
  • Great location, very clean well appointed cottage.

    Christopher2019-12-08T00:00:00Z
  • My family and I really enjoyed the space. It had everything we needed. It’s conveniently located in a central location. The kitchen was stocked with all the essentials. The owner was always available and a pleasure.

    Melina2019-11-29T00:00:00Z
  • Great location, very spacious and clean. Easy check in.

    Christopher2019-11-11T00:00:00Z
  • We were attending a wedding held at the Pridwin Hotel. Florence’s house was perfectly located nearby. It was also bright, comfortable and sparkling clean!

    Mike2019-10-06T00:00:00Z
  • Room Type

    Entire home/apt


    Property Type

    House


    Accommodates

    4


    Bedrooms

    2

    Shelter Island, NY, United States

    Located on the top floor of a 1850s home, this studio features beautiful vaulted ceilings and skylights that brighten every space. The chic white interior is elevated by soft pastel colors, wooden textures, and granite countertops.
    Recently renovated apartment in a historic home. Tons of natural light and everything about the space and home is unique!
    The home is in the center of historic Greenport making it easy to get around. See breathtaking views from the harbor, try some water activities by the beach, go for a tour of a local vineyard, and enjoy the area's great dining and entertainment options.
  • Very close to the main town which was very convenient and reasonably priced

    John2020-01-05T00:00:00Z
  • We had a beautiful time! Location was perfect. The loft was cozy and clean, the bed was so comfortable!

    Pamela2020-01-01T00:00:00Z
  • Really lovely little apartment, perfectly sized for our short getaway together. Walkable to town but nice and quiet, just a block from the local library and a 5-10 minute walk to all the stores and restaurants in Greenport. The space itself is clean, stylish, and very comfortable. We would be glad to stay here again!

    Matt2019-12-28T00:00:00Z
  • Cindy's place is ideal! Even on a blustery day, it oozes warmth and light. So comfortable, and clean. It was a true pleasure to stay there...

    Kelly2019-11-30T00:00:00Z
  • The Jewel was a fantastic place to stay for our weekend getaway in Greenport! The relaxing decor and homey atmosphere made for a perfect few days. Everything down to the shampoo in the shower was great. A quick walk and you’re in the heart of it all in Greenport as well. Highly recommend!

    Joe2019-11-18T00:00:00Z
  • This was a wonderful weekend getaway spot! Close to all things downtown Greenport and lots of wineries. They provided all the necessary toiletries and great recommendations for fun places around town. Loved our time here!

    Brycen2019-11-11T00:00:00Z
  • It's a nice place and has great styling. Quite large too. It's about a 5-7 minute walk to "downtown" Greenport. Ando's coffee is worth a visit, nice place.

    Robert2019-11-03T00:00:00Z
  • This apartment is a beautiful Bolt hole. We were very sad to leave. The shower was hot, the bed comfortable and the decor stunning. Highly recommended

    Jilly2019-10-31T00:00:00Z
  • Room Type

    Entire home/apt


    Property Type

    Loft


    Accommodates

    2


    Bedrooms

    1

    Greenport, NY, United States

    Wide open loft like space in the heart of the Heights walking distance to North ferry and Marie Eiffel market Many antiques including 1930s leather club chairs and a wonderful 1850 Swedish gustavian sofa in the living room many original pieces of art work Note :the bath tub in the master bedroom is for decoration only Shelter Island license B Zone
    This house is in a convenient location that is close to the North Ferry, as well as the shops, cafes, and restaurants on Grand. Marie Eiffel market is within walking distance.
  • Great spacious airy and light apartment in perfect shelter island location. wouldn’t hesitate in booking again!

    Jo2019-10-13T00:00:00Z
  • Jason's apartment is exceptional. It is right in the heart of Shelter Island -- you can walk to many great restaurants and cafés nearby and go on beautiful run or walk in any direction. The apartment is SO spacious. It is situation on multiple levels with enormous common areas -- beautiful high-ceiling, sunny, and well-lit living room, kitchen, and dining area. There are three very thoughtfully appointed bedrooms, and the top floor has a master suite and an additional room that make give it added privacy from the main floor, complete with a huge bathroom. The kitchen is well stocked, and there are multiple outdoor spaces -- huge balconies, including one with a grill. The place is filled with beautiful coffee table books on art, cooking, and photography, board games, entertainment, etc. We had 3 couples stay in this apartment for a weekend and it couldn't have been more comfortable. Jason was so easy to communicate with, and check-in and check-out were a breeze given the keypad entry. Thank you!

    G.2019-09-22T00:00:00Z
  • Perfect getaway! Accommodations were great!

    Patricia2019-09-11T00:00:00Z
  • The perfect location for a first timer to Shelter Island! Walking distance to multiple shops and restaurants. The rental is very spacious and open and great for small groups. Don’t forget to enjoy the patios!

    Robyn2019-09-08T00:00:00Z
  • Jason is a phenomenal host! Got back to me within minutes and was readily available to help. The apartment is even better than the photos— it’s filled with thoughtful design, feels very welcoming and inviting, and there are tons of great books too. Came with my husband, sister, and our parents. It was spacious and comfortable for all. Would wholeheartedly recommend to anyone looking for a special, relaxing getaway!

    Kate2019-09-03T00:00:00Z
  • Super stylish loft apartment in a great location. Amazing art throughout (we put a couple of bits in the cupboard as we have young kids!) and lots of space and light. Great find!

    Chris2019-08-24T00:00:00Z
  • The apartment went above and beyond our expectations: clean, comfortable. Jason was extremely communicative and was available/responsive to all our queries. We cooked on both nights. The kitchen is fully stocked with everything you might need and Jason made sure the tank to the grill was full before we arrived. Can't wait for our next stay!

    Eleanore2019-08-04T00:00:00Z
  • This place is perfectly located and so spacious! Our whole family had plenty of room to hang out inside or outside. We loved it. (Also there are a ton of great books, and cool art!)

    Jen2019-08-01T00:00:00Z
  • Room Type

    Entire home/apt


    Property Type

    Apartment


    Accommodates

    6


    Bedrooms

    3

    Shelter Island Heights, NY, United States

    Born from the name of the 75-year-old tree in the center of Greenport Village’s historic Stirling Square, this former 19th-century horse stable has been converted to American Beech Restaurant, Bar & Hotel—an updated destination for unpretentious dining and dwelling, stimulated by the vibrant North Fork region of New York. The boutique hotel features eleven Suites, including two two-bedroom apartments. The Suites combine a tropical decor with original art available for purchase from VSOP gallery.
    Each of our rooms come with a fully stocked mini-bar, Nespresso machine, Smart TV, glass shower door, iron, ironing board, hairdryer and Maison Margiela amenities. We've also included robes, Frette beach towels, complimentary yogurt & granola, and coffee pods to make your stay all the more memorable!
    American Beech Hotel's special location in downtown Greenport is walking distance from the Peconic Bay shoreline, and a bike ride from beaches on the Long Island Sound. Hotel guests have access to complimentary bike rentals and Greenport is home to a diverse collection of local businesses, including shops, cafes, restaurants and bars. The North Fork of Long Island's agricultural and aquatic landscape provides delicious ingredients for our many culinary destinations. Our local seafood is always fresh and each season here offers a variety of local activities.
  • Perfect location and crystal clean room

    Kib2020-01-21T00:00:00Z
  • Amazing location right in the heart of town. The multiple buildings creates a really nice layout with shops and restaurants all on the same property. The speakeasy is also a nice perk.

    Chris & Trish2019-08-13T00:00:00Z
  • We both adore the North Fork, a place that has that certain scent in the air that just breathes home in your lungs, and that certain light and look that grabs you everywhere you glance. As if this is not enough, American Beech brings yet something else, something beyond words really, a feeling that you would not be anywhere else in the world at the very moment you are realizing what you have found here. We snuggled in a former horse stall. How cool is that? We enjoyed the boutique, the restaurant, the mixology at the lovely bar, the ambiance of a small village all tucked in and away from all thoughts of the rest of the world, and Bella and Stephanie were born to be People people. We both love old things since only old things can have stories that have become old but were new stories when they were being made, the wonder of old things, and American Beech is the old made new, but with the old still sharing stories, and resonating perfectly with the love and attention that is everything American Beech . We will be back. As soon as possible...

    James2019-06-21T00:00:00Z
  • Room Type

    Private room


    Property Type

    Boutique hotel


    Accommodates

    2


    Bedrooms

    1

    Greenport, NY, United States

    Nestled steps from the beach, and all that Greenport and the North Fork has to offer, this exquisitely charming 3 bedroom 2 bathroom waterfront home is absolutely delightful.. You’ll love my place because of the views, the location, the people, the ambiance, the outdoors space, and the Saltwater pool.. My place is good for couples, solo adventurers, business travelers, families (with kids), big groups, and furry friends (pets).
    We are steps to the greenport boardwalk, we are on the water with stunning views of the bay, and we have a refreshing, and also heated saltwater pool.
    Greenport is known for its tourism during the summer. It has a locally famous 1920s carousel, located near the waterfront. The village is also the home of the East End Seaport Museum & Marine Foundation, which hosts the annual Maritime Festival each September. The museum is housed in the former station house of the Greenport Long Island Rail Road station, while the East end of the Railroad Museum of Long Island is located in the former freight house. The new station is the terminus of the Long Island Rail Road. Most of the tourism stems from maritime activities, as well as proximity to the more than 40 vineyards on the East End of Long Island. It has many small shops and boutiques, ice cream parlors, bed-and-breakfasts, and restaurants ranging from fine-dining to paper-napkin crab shacks. Greenport proves to be the hub of the North Fork foodie culture with many acclaimed restaurants. Lucharito's, Noah's, The Frisky Oyster, The Blue Canoe and First and South all rank among new and acclaimed restaurants on the North Fork in the village. It is also the home of the Greenport Farmers' Market, the only multi-vendor cooperative local market on the North Fork. Greenport is also home to Andy's, Claudio's Restaurant, Clam Bar and Crabby Jerry's, all three are located on the water and serve less upscale food. Claudio's Restaurant believes themselves to be the oldest single family-owned restaurant in the United States.
  • 1st time in staying for the weekend in Greenport.... Location is great and with in walking distance of everything in Greenport. Host was very accommodating and the place was clean.

    Junior2019-10-14T00:00:00Z
  • Joshua’s place is in the perfect location - very near to the cafes and bars also right across the street from the water. Apart from the construction next door, we had a lovely weekend in Greenport. Be mindful that this is a quiet little neighborhood and not the ideal place for people who are a bit younger as you will disturb the neighbors. Outside of the neighborhood, Greenport is a great town with many cute restaurants and bars.

    Jake2019-09-08T00:00:00Z
  • This was our second time staying with Joshua and we had a wonderful time. With a family of 4, the house is amazing but the back yard pool can’t be beat. The fact that main part of town is a 2 minute walk to all the amazing restaurants also makes for such a relaxing trip. Joshua was on site as well in the apartment below if we ever needed help with anything. Again an amazing summer vacation. We will definitely be back a 3rd time.

    Jennifer2019-08-01T00:00:00Z
  • This is our second time at Joshua’s house. It is a great size and the back yard is stunning. Joshua is very responsive and will help with what ever you need. We hope to come back next year!

    Amanda2019-07-28T00:00:00Z
  • This house is so cute and in a great location, close to everything in Greenport! We came for my sisters bachelorette party to go to the vineyards and it worked out great. The host did stay in the basement, which would have been nice to know beforehand. The description states that they may be in and out of the basement for legal reasons but we didn’t know they were actually staying there the whole time. Otherwise, the space is amazing and good for groups!

    Nicole2019-07-21T00:00:00Z
  • The house was perfect! Super clean, great beds, the backyard and pool were fantastic and it was steps away from the ferry!

    Janine2019-07-14T00:00:00Z
  • Lovely home, immaculate, scenic, so close to town, beautiful yard and pool..very special!

    Ellen2019-07-12T00:00:00Z
  • We had a wonderful vacation in Greenport. Josh and Tamara live on the grounds and were immediately responsive to all of our needs. They kept the pool sparkling clean and the flowers and trees well manicured. They had a beautiful welcome basket for our arrival and the house was well stocked and immaculate. The location is absolutely perfect and within a short walk to everything in Greenport. Really loved everything!

    Linda2019-07-06T00:00:00Z
  • Room Type

    Entire home/apt


    Property Type

    House


    Accommodates

    8


    Bedrooms

    3

    Greenport, NY, United States

    Brand New Modern Greenport Bungalow Located in the historic town of Greenport Village - 8 min walk to the beach, center of town, Shelter Island Ferry and LIRR... A newly built sun filled 3 bedroom house with all the amenities you would need when renting a home. Enjoy the large and fenced in back yard after a fun day in this historic Long Island fishing village. Great restaurants, and even better locally produced wine and beer!
    Our master bedroom has a beautiful master bathroom and walk in closets behind the sliding barn doors. The house is filled with light, so even on those cold winter days, our home is filled with natural light and a warm summer vibe :)
    What we love about our neighborhood is the easy access to the beach, center of town, and shelter island ferry. We are walking distance to everything! We are also a 10 min bike ride to kontakosta winery if you'd like to go for a tasting :) As past Brooklynites, we understand the desire to be near public transportation and not be bothered with the hassle of renting a car. Our home is a 5 min walk from the LIRR and the Jitney! The location of the house is walking distance to everything and taxi's are also available if you desire to venture out a bit further :)
  • Lovely little place to spend a weekend or so out in Greenport. Would recommend.

    Christopher2020-03-15T00:00:00Z
  • Gorgeous little bungalow in Greenport! Thoughtfully decorated and comfortable for four adults. Loved our weekend here.

    Scann2020-03-08T00:00:00Z
  • beautiful, well designed space close to everything!

    Colin2020-03-01T00:00:00Z
  • Jillian’s place is beautiful, clean and in such a great location! She was quick to respond and gave great suggestions for the area. Thank you so much for a great evening away :)

    Merren2020-02-22T00:00:00Z
  • Can wait to book again! It was exactly what we needed for two couples!

    Chris2020-02-17T00:00:00Z
  • This was the perfect place for a couples getaway! We each had our own room and bathroom. It was very spacious, stylish and clean. We enjoyed everything about this bungalow home and our host Jillian was wonderful. She was thoughtful, recommended several activities, restaurants and local bars to us. She was also very responsive. We can’t wait to come back this Spring/Summer! Thank you Jillian. Highly recommend her bungalow in Greenport! Xo

    Shawnie2020-01-19T00:00:00Z
  • We had a wonderful time celebrating my son's birthday. Jillian's home was simple, clean and very welcoming. And Jillian was so responsive and accommodating! Thank you for a memorable weekend!

    Ellen2020-01-12T00:00:00Z
  • Jillian’s place was exactly what our group needed for a weekend out in Greenport. A short walk to town on a low traffic block. The house was very clean and had great amenities. We would love to stay here again in the future.

    Jessica2019-12-08T00:00:00Z
  • Room Type

    Entire home/apt


    Property Type

    House


    Accommodates

    6


    Bedrooms

    3

    Greenport, NY, United States

    Popular homes

    Popular homes
    Perfectly situated just past the Island Boatyard and Salt in a peaceful neighborhood surrounded by water on 3 sides. 4 town landings and beach access across the street. Newly renovated gourmet kitchen with large island and beautiful marble counters. 3 bedrooms upstairs and private office off of master suite, a 4th bedroom on the first floor and finished basement with full bathroom. Use if two kayaks and paddle board make this the perfect getaway retreat!
    Guests can use the entire house including the new private office off the master suite. There’s a first floor bedroom with queen sized bed as well as 3 bedrooms upstairs ( master has king sized bed, guest 1 has full sized bed and guest 3 has twin beds). Large finished basement perfect for recreation room.
    Quiet and peaceful with gorgeous water views everywhere...lovely for walking around.
  • Beautiful and clean house with the kitchen of my dreams! Perfect space for two families and a great backyard space. Easy to get to and was the getaway we needed

    Michelle2020-02-18T00:00:00Z
  • We had a great stay for a long quiet Fall weekend with our friend and her toddler. We absolutely loved the big kitchen — cooked quite a bit. And if it had been warmer, I’m sure we would have spent lots of time out on the deck by the pool. Definitely recommend.

    Michael2019-10-14T00:00:00Z
  • Karen’s place was exactly as pictured, very quaint and relaxing .... exactly the weekend away from the city that I needed. Karen was a gracious host and responded quickly to all my questions. We will definitely be returning !!

    Joli2019-10-01T00:00:00Z
  • This house is perfect for couples and families. There is ample dining space inside and out with a cooks kitchen that is well appointed and an outdoor grill. The pool is sundrenched all day! It is a short distance to public beaches. There is a local grocery store nearby. A great place to spend time outdoors. Karen provides everything one might need for a wonderful getaway!

    Lisa2019-09-12T00:00:00Z
  • Karen's place is excellent. It felt like home and we had an amazing time in Shelter Island. The backyard was perfect for activities and the house had an excellent set up for multiple couples.

    Bonsal2019-06-23T00:00:00Z
  • The house was spacious, stylish and clean and would be comfortable for a large group, though there were only 2 of us. The pool is beautiful and private. There are water views from the master bedroom upstairs. We enjoyed using the two kayaks — there are a couple entry points within carrying distance if you are fairly strong. Shelter Island is very low key and great for kayaking! There are also some good (and pricey) restaurants on the island. We also enjoyed exploring nearby Greenport, Sag Harbor and Montauk - easily reachable by ferry/car. Unfortunately, the weather was not on our side, otherwise we would have spent a day or two on Cresent/Sunset beach on the island. We did go to the Pridwin and catch an amazing sunset. Recommend!

    Portia2019-06-20T00:00:00Z
  • This house was absolutely perfect! Couldn’t have picked a better place!

    Taylor2018-10-15T00:00:00Z
  • Fabulous house with many amenities. Couldn't have wanted more! Definitely a "be back" experience.

    Susan2018-09-10T00:00:00Z
  • Room Type

    Entire home/apt


    Property Type

    House


    Accommodates

    6


    Bedrooms

    5

    Shelter Island, NY, United States

    -Close to everything, three blocks to S.I. ferry and L.I. train, and short walk to beach and village. -Two and a half rooms, one bedroom, one bathroom with stand up shower, new construction. Lower level, separate entrance and just eight steps down to door- all brand new -Off street parking available -No smoking -Access to outside shower and pool
    Our neighborhood is part of the Village of Greenport. It is a historic whaling and bootlegging beach community. There are many art galleries, farm to table restaurants, pubs and bars within walking distance of the house. There is a great Roller Skating rink, Carousel, Large park (Monday night free dance parties with live bands all summer) many marinas and wonderful shops that you can walk to from the house. Above all, Greenport is part of the North Fork Wine Country, home to over 35 vineyards plus home to many breweries. You can see the grapes and hops growing along the main roads (with the strawberries, lavender, potatoes, and many more veggies). You can fish from the beach at the end of 6th Street or from the Village docks or go on board a fishing charter boat in Peconic Bay.
  • Wonderful stay. So many thoughtful touches throughout the space that made it extra inviting. Easy access to the downtown and train station, which was ideal since we didn't have a car. We will have to come back when the weather is warmer and use the pool!

    Addie2019-10-27T00:00:00Z
  • Nothing but good things to stay about our stay. Really enjoyed being near the beach/playground and the bed was super comfy.

    Brian2019-10-06T00:00:00Z
  • Emily's place is spectacular. Stayed 2 nights for a wedding, it was perfect. It is a 8 minute walk into town and the water is literally down the street. There were bikes to borrow free of charge. Extremely clean and more spacious than I expected. Would stay here again and definitely recommend!

    Matthew2019-09-22T00:00:00Z
  • Cozy and comfortable! This was the perfect home base for a weekend in Greenport. Perfect location and very hospitable hosts.

    Tanza2019-09-15T00:00:00Z
  • Our entire stay was fantastic! I loved every detail of the place and felt so at home. Emily and her family were so welcoming and were there if we needed anything. We had such a nice stay, and would recommend this place to anyone wanting to stay in Greenport. We could easily walk downtown or take a quick walk to the North Ferry. You will not be disappointed staying here!

    Alessandra2019-09-08T00:00:00Z
  • The nautical themed everything was so adorable- even better in person. The apartment is in a great little neighborhood and it was fun to borrow the bikes to get around town. We'd stay here again next time we find ourselves in Greenport.

    Elizabeth2019-09-03T00:00:00Z
  • Our stay at Emily's home was even more beautiful than we had expected. You can tell that the family puts in every effort to add amazing little finishing touches on all of the place's amenities. My husband and I were perfectly comfortable and had a great relaxing weekend enjoying the pool and walking to downtown Greenport for food and entertainment. We felt welcomed immediately and had a completely hassle free stay. Would love to come back and would rate this in the top 5 of all my airbnb experiences.

    Patricia2019-09-01T00:00:00Z
  • We loved staying here. It was very close to town and just a short walk to the beach. The attention to detail with in the apartment was amazing. Beautiful location. They are very knowledgeable on the area and there is a book they made that tells you about all the local places to see and all the different restaurants. Highly recommend staying here it was fantastic !

    Amanda2019-08-27T00:00:00Z
  • Room Type

    Entire home/apt


    Property Type

    Apartment


    Accommodates

    4


    Bedrooms

    1

    Greenport, NY, United States

    Start the morning with a cup of coffee on the shaded backyard deck while listening to the birds in the chestnut tree. This newly renovated 1835 home retains its historic charm and several period features, complemented by coastal-themed artifacts plus turquoise and bright blue accents.
    The house is located on a .35 acre lot with plenty of outdoor dining space and a huge grass area with a firepit & hammock. There are 2 floors. The first floor has an open floor plan with a connecting kitchen, dining room, and living room. The kitchen is well equipped with a dish washer, electric stove/oven, refrigerator, and coffee bar. There is also a bedroom on the 1st floor with 2 full-sized beds. The 2nd floor has 3 bedrooms and a loft/den area. The three bedrooms on this floor have 1 queen bed+futon, 2 full-sized beds, and 2 twin beds (which can be made together to form a king upon request), respectively. All rooms have AC. There are 2 full bathrooms (1 on each floor) and a washer/dryer.
    Greenport was voted one of the prettiest towns in America by Forbes magazine. It has a vibrant and relaxing culture, offering access to beaches, wine tasting, and wonderful restaurants. The Shelter Island Ferry and Hampton Jitney stops are nearby.
  • Great location and a wonderful house. We will definitely stay there again.

    Chase2020-01-01T00:00:00Z
  • Great house and area. Loved the cheese shop and oyster shack in town. Everything was convenient.

    Anne2019-11-30T00:00:00Z
  • We had a great time at The Greenport Townhouse and it was an excellent pick for our weekend with 7 girls. Check-in and out was a cinch and the location couldn’t be beat as it was a close walk to the train station and everything fun in town. The home was clean and spacious, with a great backyard, and George was a terrific host - always responsive, helpful, and gracious. Would definitely stay here again!

    Hillary2019-11-17T00:00:00Z
  • Great pick! The owner was more than helpful and checked in throughout the stay to be sure we didn’t need anything. The house is spacious, clean, comfortable, and well decorated. We were walking distance from all restaurants and shopping and a quick car ride from wineries. Needless to say, we enjoyed our stay and were more than happy with the house itself.

    Michelle2019-11-11T00:00:00Z
  • A wonderful house near downtown Greenport - perfectly slept our group of girls with everyone in their own bed space and with access to a full bathroom. The house is thoughtfully decorated , full of open common space and has a BEAUTIFUL backyard with a fire pit and seating. We felt comfortable cooking here and made ourselves right at home. The best part was we were not but a 5 minute walk to the adorable downtown that is Greenport - it was an easy check in and check out process (George even let us check in a bit early) and the house was stocked with sheets, towels, blankets etc. The only complaint we had was the lack of paper towels, the broken Coffeemaker and a lack of a sponge for dishes. All minor things that really just didn't enable us to clean as much as we would normally. Would highly recommend this spot to anyone.

    Moll2019-11-04T00:00:00Z
  • This was the absolute perfect place for our weekend in Greenport. The place is spacious and beautifully decorated. We had more than enough room and it was walkable everywhere! The town is so cute and George provided wonderful recommendations. Check in and out was a breeze and George answers any questions right away! I can’t say enough about this perfect rental. I would 100% stay here again and recommend to anyone!

    Lauren2019-10-21T00:00:00Z
  • The Greenport Townhouse is located steps from everything you want to see and do in Greenport, yet removed from the main drag. The house is huge with super comfortable and private bedrooms and several sitting areas as well. The decor is fun and beachy and I can’t wait to come back here.

    Eva2019-10-03T00:00:00Z
  • We loved this house during our long weekend in Greenport! The house is in a great location, only a few minutes to walk into town; it’s clean, spacious, comfortable and has a great backyard! The host was quick to respond to any inquiries we had while we were staying there, and communication throughout booking and our stay was clear and respectful. Would definitely book again!

    Katherine2019-09-30T00:00:00Z
  • Room Type

    Entire home/apt


    Property Type

    House


    Accommodates

    12


    Bedrooms

    4

    Greenport, NY, United States

    An architect's and interior decorator's dream home! This home is a historic boathouse built in the late 1890's, and recently & lovingly fully renovated and restored. In the middle of Greenport Village - walking distance to train station, Jitney stop, and Shelter Island Ferry as well as the best North Fork restaurants, vineyards, bars, and beaches. Two bedroom home with ground floor fireplace, outdoor shower (not enclosed), and beautifully landscaped outside patio w/grilling & dining areas.
    The living room and kitchen have enormous original boathouse doors that swing open and create a unique indoor/outdoor space, perfect for putting on a record and relaxing and reading with a breeze in the sunny mornings, warming yourselves by the fire, or cooking and enjoying a glass of wine on the outdoor grill and in the kitchen. Enjoy a glass of wine and a good book on any of the three (3!) outdoor areas including adirondack chairs and porch swing, yet still be only a 2 minute walk to all that the village has to offer.
    The house is central to all Greenport Village has to offer, including being less than .2 miles from the charming shops, farm to table restaurants, and cocktail bars. It is also .1 miles away from the water at Sterling Marina at the end of the street, and 1.5 miles away from Gull Pond Beach (makes a nice morning walk). In addition one of the best vineyards on the North Fork, Kontokosta, is only a mile away.
  • House was exactly as described. Extremely clean, walking distance from all the good spots in town, had everything we needed inside and Brian was responsive and a pleasure to deal with throughout.

    Gavin2020-02-16T00:00:00Z
  • Our stay at Brian’s house was a delight. The house is sparkling clean and full of style and charm, and it’s located just a short walk away from Main Street’s shops, restaurants, and bars. Brian is a thoughtful and communicative host. Would highly recommend and would love to stay again!

    Laura2020-01-01T00:00:00Z
  • The Boat House is just beautiful and totally lived up to expectations and more. Brian is a very responsive host and attentive to any questions we had. Check in and check out very smooth. The house is impeccable - beautifully decorated, cozy while spacious with a lovely layout. The morning light in the living room is enchanting. It’s super charming all round!!! It’s extremely comfortable with everything you could possibly need. We greatly enjoyed using the log fire in the evenings after a short stroll out for dinner. All amenities are a stones throw away while the house itself is on a very quiet and secluded road. We’ll definitely be coming back!!!

    Suzanne Hope2019-12-01T00:00:00Z
  • An amazing house, timeless, beautiful touches, great natural light, very nicely laid out. This was the highlight for us of a fortnight travelling around the States. Comfy beds, an open fireplace, leafy privacy, and a beautiful old building.

    Mark & Liam2019-10-28T00:00:00Z
  • Beautifully styled and clean, comfortable space in the most perfect location for exploring Greenport Village. Communication was easy and Brian was very helpful with local recommendations and thoughtful touches. We loved our stay - thank you!

    Kylee2019-10-14T00:00:00Z
  • We LOVED this adorable home. The most comfortable and well adorned. I rarely add a review, but seriously worth the stay. You will want to buy this place! Amazing! Huge thanks to our hosts for everything - our stay here was fantastic.

    Megan2019-09-15T00:00:00Z
  • This house is a perfect home base for spending vacation time on the East End. The well-appointed, beautifully restored boathouse is on a quiet street within steps of the heart of Greenport village. It was wonderful spending summer evenings on the patio and with the large doors open to enjoy the breeze. We had excellent communications and helpful tips from the host throughout the process. We hope to be back soon!

    David2019-08-02T00:00:00Z
  • This house is as good as it appears in the pictures, if not better. The architecture and remodeling are superb, the windows and ceiling heights are beautiful and the outdoor spaces are charming and comfortable. As other reviewers have noted, the house is spotlessly clean, the furniture is comfortable, the house is well located to downtown Greenport (on a quiet street) and Brian (the host) is helpful and professional. Highly recommended!

    Geoffrey2019-07-23T00:00:00Z
  • Room Type

    Entire home/apt


    Property Type

    House


    Accommodates

    4


    Bedrooms

    2

    Greenport, NY, United States

    Born from the name of the 75-year-old tree in the center of Greenport Village’s historic Stirling Square, this former 19th-century horse stable has been converted to American Beech Restaurant, Bar & Hotel—an updated destination for unpretentious dining and dwelling, stimulated by the vibrant North Fork region of New York. The boutique hotel features eleven Suites, including two two-bedroom apartments. The Suites combine a tropical decor with original art available for purchase from VSOP gallery.
    Each of our rooms come with a fully stocked mini-bar, Nespresso machine, Smart TV, glass shower door, iron, ironing board, hairdryer and Maison Margiela amenities. We've also included robes, Frette beach towels, complimentary yogurt & granola, and coffee pods to make your stay all the more memorable!
    American Beech Hotel's special location in downtown Greenport is walking distance from the Peconic Bay shoreline, and a bike ride from beaches on the Long Island Sound. Hotel guests have access to complimentary bike rentals and Greenport is home to a diverse collection of local businesses, including shops, cafes, restaurants and bars. The North Fork of Long Island's agricultural and aquatic landscape provides delicious ingredients for our many culinary destinations. Our local seafood is always fresh and each season here offers a variety of local activities.
  • This place was great, from the front desk personnel, the bartender of the black llama; their on site cocktail lounge; to the knowledgeable suggestions provided on where to go and what to do. Everything was more than I had expected and I highly suggest anyone thinking of a place to stay in Greenport to give American Beech a go, you won't be disappointed

    Aaron2020-02-23T00:00:00Z
  • Cozy, fun, central. All you need or can ask for in Greenport. Wonderful hosts, amazing stay!

    Mj2019-11-30T00:00:00Z
  • This is a trendy place in the heart of Greenport. The room was nice and we enjoyed the convenience of walking around town.

    Sean2019-08-30T00:00:00Z
  • Room Type

    Private room


    Property Type

    Boutique hotel


    Accommodates

    3


    Bedrooms

    1

    Greenport, NY, United States

    Explore the historic seaport of Greenport Village from this recently remodeled 1-bedroom, 1-bathroom vacation rental apartment. Comfortably sleeping 2 guests, this home is ideal for guests seeking a cozy retreat. Located in the heart of downtown, you won’t find a better location to explore all the area has to offer than from this charming apartment. Only 2 blocks from Main Street, enjoy quick access to numerous antique shops, exceptional seafood restaurants and an abundance of activities!
    Bedroom: King Bed Decorated in warm tones and modern furnishings, this quaint Greenport vacation rental apartment is sure to feel like your ultimate home-away-from-home getaway. Enter the apartment through a spacious great room that encompasses the kitchen, dining and living areas. Featuring a flat screen smart TV with Netflix and streaming capabilities along with a leather sofa and matching armchair, the living room is the perfect place for you and your travel companions to unwind after long days out and about. Prepare home cooked meals in the fully equipped kitchen opposite the living area that features brand new stainless steel appliances. Enjoy your creations at the dining table set for 4 that lies between the kitchen and living space. The bedroom boasts a king bed and large closet, along with a lovely, recently renovated bathroom that includes a pristine vanity and walk-in shower.
    Enjoy the convenience of a prime downtown location along with the peace and quiet of being in a residential area. Only 2 blocks from Main Street, you don’t have to travel far for incredible shopping and dining. Head down the street to Sterling Creek and spend some time on the water. Watch the boats flow in and out of Greenport Harbor and go for a swim off the dock. Hop a ferry over to Shelter Island and enjoy an abundance of activities including swimming, fishing, boating, hiking and golfing.
  • Great location, super easy walk to the town, which was great because we got some cold weather. Loved the floors, and amount of space that we had. Recommend staying here.

    Christopher2019-11-10T00:00:00Z
  • Very clean and in the perfect location.

    Sara2019-10-21T00:00:00Z
  • My fiancé and I stayed here during our wedding weekend in Greenport and it was just perfect. The spacious and charming apartment gave us the opportunity to prepare for our wedding in comfort and ease. The location was wonderful- on a quiet street but within short walking distance of everything we needed. The space is as advertised- full kitchen, large bed/bedroom, and spacious bathroom and living room. But it’s even more lovely than the photos. Plus, John had a special welcome at check in to celebrate our wedding. We didn’t want to leave and will definitely come back to stay next time we’re in the area!

    Joanna2019-10-13T00:00:00Z
  • Great place and great host. Excellent value for the location - everything was walkable. Would book again if in the area.

    Cathy2019-08-25T00:00:00Z
  • Loved staying here everything was awesome! Would definitely recommend.

    Tiffany2019-05-26T00:00:00Z
  • We really enjoyed our stay at this lovely home! We will definitely recommend it to friends and family that are thinking about visiting Greenport. You can't beat the location!

    Sarah2019-05-05T00:00:00Z
  • Such a great apartment in the perfect location for a weekend stay in Greenport. The space was super clean and fully equipped. We were able to walk all over town and will definitely be back! Thoroughly enjoyed our time in Greenport!

    Meri-Leigh2019-04-21T00:00:00Z
  • Great location and awesome apartment!

    Rebecca2018-10-28T00:00:00Z
  • Room Type

    Entire home/apt


    Property Type

    Apartment


    Accommodates

    2


    Bedrooms

    1

    Greenport, NY, United States

    Cozy, quiet, newly renovated cottage on the picturesque Menantic Peninsula. Located on a Shelter Island historical landmark (The Lord's Shipyard), and perfect for families or couples looking for a quiet paradise nestled in nature on the sea. 5 minute walk from the Island Boatyard and excellent restaurants, and a 5 minute drive from Sunset Beach. Sea views from every room and bathroom. Stunning sunsets every evening visible from the back porch.
    Brand new space, renovated this year (2018). Central air-conditioning and heating in every room, screens and shades on all windows/doors. Located on a 10-acre, seaside estate with sea views from every room. Laundry service if booking a week long stay or longer.
    Quiet residential area nestled in nature, with quaint restaurants, beaches, and cafes. Great for biking, walking, swimming, and relaxing.
  • excellent getaway cabin, gorgeous water views, great little comfort touches, Maghnus and Aimée were responsive and sweet. Lovely stay!

    Carvell2019-11-26T00:00:00Z
  • Maghnus’s place is clean and has everything you need and he was very responsive. We have a great stay.

    David2019-11-11T00:00:00Z
  • The house is beautiful as pictured. A great place for two couples to stay, with a relaxing backyard and within a short drive of beaches. Kitchen is also week equipped for those who like cooking or grilling.

    Elizabeth2019-10-07T00:00:00Z
  • The Lord Shipyard Cottage was absolutely perfect for a mother-daughter visit to Shelter Island. The cottage was well-laid out for us to share, with a comfortable living/kitchen area, private bedrooms and bathrooms, and a lovely deck and yard to enjoy. The location was serene and private while convenient to beaches, restaurants, and all the nature and beauty of the island. Would definitely recommend and would love to return.

    Emily2019-10-01T00:00:00Z
  • My wife and I went out during the week in late August. The house is tucked away from the road, overlooking beautiful waterways with a really nice front lawn. Hosts are very friendly and accommodating (by airbnb/text message). Overall, we had everything we needed and really enjoyed our stay. We could hear the construction next door during the day, but weren't there much as we were exploring beaches, town, etc, and all was quiet by late afternoon for sunset on the water. Thanks for the hospitality. We'd certainly come back.

    Chris2019-08-30T00:00:00Z
  • The cottage was set up perfectly. Bedrooms were comfy. Kitchen had everything we needed. And the whole house smelled great!

    Steve2019-08-25T00:00:00Z
  • Maghnus is a great host and his cottage is lovely. Great communication before, during and after. Will be back!

    Andrea2019-08-18T00:00:00Z
  • Awesome place. Gorgeous location. Hosts communicate fast and are very helpful. Thank you!

    Sholem2019-08-11T00:00:00Z
  • Room Type

    Entire home/apt


    Property Type

    House


    Accommodates

    4


    Bedrooms

    2

    Shelter Island, NY, United States

    Mornings at the beach, afternoons by the pool...sunset dinner on deck w/ water view. Luxury beach house great for families. Sleeps up to 8. Chef’s kitchen w/Wolf, Sub Zero and wine fridge. Lg swimming pool with hot tub. Shaded upper deck with grill seats 8+ for dinner. Fireplaces. Outdoor gym*. Kids’ tree house. Central a/c. 3 minute walk to Wades Beach. Walk to Mashomack Preserve. *Available for entire summer OR monthly May - LD* (message us for off season!). Reg#19L-0121
    Bright and airy beach house with skylights, views and fireplaces. Modern and clean interior, whitewashed floors, high end finishes throughout. Cosy den with fireplace. Three bedrooms, two ensuite. Additional sleeping capacity with double pull-outs in den and in semi-common alcove. Top-of-line kitchen: Wolf/Sub Zero. Large dining / living room with views and fireplace. Three full bathrooms, powder room, outdoor shower. Heated swimming pool. Hot tub.
    Shelter Island is quiet, beautiful, unspoiled and surrounded by water with many beaches, easy water access. Perfect for kayaks, paddle boards, swimming, sailing, biking. One third of the land is nature preserve with trails, visitor center and events. The island has restaurants, cafes, bars, a brew-pub, charming shops, public golf, mini-golf, a supermarket and a drugstore. Island summer events: - Shelter Island 10-K on June - July 4th fireworks on July - Sylvester Manor Farm to Table Dinner June - Shakespeare at the Manor July - Mashomack Preserve Benefit July - Shelter Island Yacht Club Race Week Aug
  • Everything was even better than the photos. We were 2 families (4 adults and 4 kids) and the layout and amenities were perfect. I didn't see a mention of the playset in the backyard in the description so was pleasantly surprised to find that. The kids loved the treehouse and the adults loved sitting in the hot tub on a chilly night. The house was super clean, the beds very comfy and the location was fantastic. We loved being able to walk around the corner to Wades Beach and Shelter Island in the fall is lovely. Overall would love to come back again and again!

    Helen2019-10-20T00:00:00Z
  • Had a wonderful stay at this home. It was clean, perfect location and great outdoor space. Would definitely stay here again!

    Renee2019-09-22T00:00:00Z
  • A dream vacation home!! It had something for everyone on a family vacation and we would love to come back. The space is luxurious and sumptuous yet comfortable and warm at the same time. Pool and hot tub were comfortable and relaxing. All of the amenities were available for use. Kim and Scott were responsive, approachable and warm property managers. Appreciated direct and fast communications with them and JC, the owner.

    Jing-Yu2019-09-16T00:00:00Z
  • Lovely holiday home a great low key trip with friends. We stayed by the pool and walked to the beach and got very lucky with weather.

    Rebecca2019-08-04T00:00:00Z
  • J.C. and his property manager were responsive and helpful. The property was pristine and well appointed. We had a wonderful time.

    Yeida2019-08-01T00:00:00Z
  • You can expect a beautiful comfortable home and a clean nice pool.

    Yelena2019-07-21T00:00:00Z
  • This place is perfect for a Shelter Island trip - closely located to the South Ferry, fantastic house with everything you need. Check-in and check-out is well coordinated and JC was very quick to answer all questions. We received tons of tips for Shelter Island, which was very helpful. The pool, kitchen and the rooms are clean, modern and beautifully furnished, and invites to just stay at home and enjoy the 2 decks and the house. We’d definitely go back!

    Haeky2019-07-15T00:00:00Z
  • Great house!

    Lynda2019-07-11T00:00:00Z
  • Room Type

    Entire home/apt


    Property Type

    House


    Accommodates

    8


    Bedrooms

    4

    Shelter Island, NY, United States

    One story waterfront cottage Wood burning stove, washer/dryer Fridge. Bath with shower. Tastefully Furnished Non-Refundable listing, Strict Cancellation policy.
    Guests are invited to enjoy The deck grounds and dock
    Cottage is situated on 2 Acres Quiet neighborhood, great for biking and jogging. Close to Beautiful beaches. Beautiful Sunrise outside your cottage window
  • Such a beautiful secluded spot on Shelter Island. Maureen is a lovely and generous host and we would love to stay here again.

    John2020-03-20T00:00:00Z
  • Awesome place for a weekend getaway. Only stayed one night but wish we were able to stay longer. Highly recommended, would absolutely stay here again!

    Ron2020-03-01T00:00:00Z
  • Had a wonderful stay. Super clean and a great view

    David2020-02-11T00:00:00Z
  • What a beautiful space and great host! Perfect for a getaway with your pup, the accommodations were beyond our expectations: spotless, awesome views, great location for walks to the beach, lots of character. We will be back, thank you Maureen!

    Guillermo2020-01-28T00:00:00Z
  • My husband & I had such an amazing weekend here. The cottage was heaven. We will absolutely be back!

    Dana2020-01-19T00:00:00Z
  • Amazing waterfront view. Efficient space with everything you need including a few things you didn’t realize you needed. Host is kind and accommodating always happy to help. We enjoyed our stay.

    Jerry2020-01-12T00:00:00Z
  • Reading all the raving reviews of Maureen’s cottage, it was hard to imagine our stay being as amazing as everyone described. But boy was it!! The cottage is beautiful, cozy and charming. Maureen greeted us warmly and was there every step of the way to answer any questions and help us out with anything we needed. The location is stunning!! Right on the water, with beautiful sunrise and sunsets. Our dog was in heaven! We loved playing games by the fire (that was set up for us with all the wood we would need), and sleeping in the very comfortable bed. Meeting Maureen and her sweet pup Willow was one of the special perks of this stay. We highly recommend and will be coming back!

    Suzannah2020-01-01T00:00:00Z
  • This was so quaint and the perfect setting for a weekend away to unwind. Maureen was so lovely and had great local tips. The place was spotless, bed comfortable, a working fire place and above all that... the view!! Perfect for a romantic weekend away. We‘ll be back

    Nathan2019-11-03T00:00:00Z
  • Room Type

    Entire home/apt


    Property Type

    Cottage


    Accommodates

    2


    Bedrooms

    1

    Shelter Island, NY, United States

    This beautifully renovated Shelter Island GEM Farmhouse is perfect for some peace and quiet! Centrally located on the island, you can reach beaches 5 minutes away or walk to the creek. Rent a bike and explore nature! Walk to the near by bakery, mini market, Chase bank or restaurants. This house has 3 bedrooms and 2 bathrooms with a full size kitchen with bar area and large living room and dining room area.
    This house is fully newly renovated with central heat and air conditioning. Wonderfully quiet location!
    This neighborhood is unique and a block away on Duvall, there are tennis courts. It's first come first serve! Picozzi station you can rent bikes. There is no grill. The liquor store you can walk to. And IGA is the grocery store you can drive to.
  • Beautiful island and a lovely home. The beds were fabulous and everything was very clean. We look forward to another extended stay.

    Patty2019-09-15T00:00:00Z
  • We loved Lynn’s place. It was centrally locates (close to the reserve, ferry, multiple beaches, etc). The home was spacious with comfy beds and a great couch. We had a wonderful stay!

    Hannah2019-09-02T00:00:00Z
  • Lynn house was incredible! My mom and friends enjoyed it tons. Comfortable for 6 people, amazing to stay in and cook a nice dinner, out door breakfast and close to everything. Lynn answered all my million questions and worked with me on my check in time. I can’t wait to come next year!

    Alex2019-08-04T00:00:00Z
  • Five of us came to Shelter Island to visit family who have a place on the island but not enough room to for all of us to stay there. Lynn’s farmhouse was perfect for our needs—adorable, very clean, and in a great location. Really fun place to stay while you explore the beauty of Shelter Island.

    Lara2019-07-28T00:00:00Z
  • This house is beautiful, and centrally located on the island. Everything about it was great.

    Andrew2019-07-21T00:00:00Z
  • Lynn's place is great; quick to respond. The house is spacious. Very quiet. AC works great. Porch is great. Beds are very comfortable. Plenty of towels including beach towels. Walking distance to many things. Checkout the Farmer's market on Saturdays. One of our best stays on Shelter Island. I would not think twice about booking again!

    Suzy2019-07-15T00:00:00Z
  • The place was very quaint and nice and to echo everyone else's comments Lynn was a true gem and a fantastic host. The place was immaculately clean and located right in the middle of the island which was nice. Would recommend to anyone and of course would check availability for any of my future visits back to Shelter Island.

    Soren2019-07-07T00:00:00Z
  • The house is very beautiful, spacious with outstanding furniture selection and detailing. We had a very good time cooking and relaxing. Centrally located in SI the house is in walking distance to local eateries and to the supermarket. Thank you Lynn!

    Alessandra2018-09-03T00:00:00Z
  • Room Type

    Entire home/apt


    Property Type

    House


    Accommodates

    6


    Bedrooms

    3

    Shelter Island, NY, United States

    Born from the name of the 75-year-old tree in the center of Greenport Village’s historic Stirling Square, this former 19th-century horse stable has been converted to American Beech Restaurant, Bar & Hotel—an updated destination for unpretentious dining and dwelling, stimulated by the vibrant North Fork region of New York. The boutique hotel features eleven Suites, including two two-bedroom apartments. The Suites combine a tropical decor with original art available for purchase from VSOP gallery.
    Each of our rooms come with a fully stocked mini-bar, Nespresso machine, Smart TV, glass shower door, iron, ironing board, hairdryer and Maison Margiela amenities. We've also included robes, Frette beach towels, complimentary yogurt & granola, and coffee pods to make your stay all the more memorable!
    American Beech Hotel's special location in downtown Greenport is walking distance from the Peconic Bay shoreline, and a bike ride from beaches on the Long Island Sound. Hotel guests have access to complimentary bike rentals and Greenport is home to a diverse collection of local businesses, including shops, cafes, restaurants and bars. The North Fork of Long Island's agricultural and aquatic landscape provides delicious ingredients for our many culinary destinations. Our local seafood is always fresh and each season here offers a variety of local activities.
  • Clean, great location

    Joe2019-08-16T00:00:00Z
  • Room Type

    Private room


    Property Type

    Boutique hotel


    Accommodates

    2


    Bedrooms

    1

    Greenport, NY, United States

    For those seeking a peaceful, quiet, zen-like place to spend their vacation or honeymoon, 'The Shelter Island Hideaway Beach Vacation Cottage' is the home for you. The luxurious, waterfront 2-bedroom, 1-bathroom vacation rental cottage offers 1,125 square feet of sheer Caribbean-style elegance. Featuring 3 waterfalls, 2 Roman dipping pools, and a 75-foot Koi pond, this romantic Hampton’s hideaway promises up to 5 guests a vacation to remember in the Estate Section of Shelter Island.
    *NOTE: Your safety matters. An exterior security camera is located at the front path, facing out towards the entrance. The camera does not look into any interior spaces* Master Bedroom (Upper Level): Queen Bed | Bedroom 2 (Lower Level): Queen Daybed, Full Pullout Bed | Additional Sleeping: Queen Air Matress This private hideway was chosen among 100's of homes to be part of CBS TV show, "The Price is Right." A one week stay at this beautiful cottage was part of the Showcase Showdown game - so by booking this property, it's like you won the game, and most importantly, a memorable stay at 'The Shelter Island Hideaway Beach Vacation Cottage!' Designed and built by an international travel editor to capture an authentic Caribbean essence, 2 levels of blissful living space, 2 multi-sided gas fireplaces, and spectacular outdoor amenities shape this secluded seaside oasis. ‘The Shelter Island Hideaway Beach Vacation Cottage’ offers a serene escape for romantics, writers, and artists, or those seeking a quiet place to meditate, practice yoga, be inspired or simply relax. Ceramic tiles cover the floors extending to an open sunroom where custom hand-laid bluestone fill the covered area, perfect for meditation. This room is enclosed by 3 sides of French glass doors for real indoor/outdoor living, leading to the outer covered pergola, where you can dine or dangle your feet in the fresh waters of either pool, surrounded by the calming sound of 3 waterfalls. The first level is an open concept floor plan encompassing the kitchen and French glass-enclosed sunroom with cathedral ceiling and Full Size Day Bed, as well as the kitchen, office area with desk and WiFi, a lovely first-floor bath, living room area with sleeper sofa. A fully equipped kitchen includes a 4-burner oven, dishwasher, blender, toaster microwave oven and coffee maker. There is also a glass breakfast area overlooking the pond, private fenced-in yard, dipping pools and waterfalls. For added luxury, the property offers a brand new well, which provides travelers with clean, mineral-free water. Sit, talk, listen to music, read or entertain in the living room. An office area looks out to the second pool - slide the French glass doors open, and the beautiful grounds meet your eye beyond the pool. The office provides high-speed WiFi and has a hand-painted armoire, a large glass desk, and an iPod/iPhone stereo system. There is a full-sized washer and dryer hidden away in a closet for your added convenience. In the sunroom, a Royal Dutch daybed sleeps 2, just inches from the water. Though the property is secluded, there are bamboo shades you can close if additional privacy if desired. Up the hand-painted spiral staircase is the master suite decorated with elegant European country cottage design. Slip into the comfortable queen-sized bed and look up to starry nights through the skylight or enjoy a bedtime film on the flat-screen TV. A magnificent 2-sided custom tile gas fireplace is visible from the bedroom and through the bathroom, where fireside bubble baths are welcomed in the luxurious Jacuzzi tub. Be carried away in beautiful outdoor spaces, complete with rushing waterfalls and stunning grounds. Eastern influenced landscaping includes beach grasses, mature Russian olive trees, fruit trees and Bamboo for added ambiance. At a moment’s notice, you can dip your feet into either of the two Roman dipping pools accessible through one of 16 French glass doors. Look out to the pool's waterfalls, or refresh yourself with a rinse in the private hot and cold running water outdoor shower. The 75-foot Koi pond has a large 6-foot natural rock rushing waterfall, whose sounds can lull you off. For nature lovers, you can admire the Goldfish and Koi as frogs leap past, turtle's surface, bunnies hop by, and birds (more than three dozen species on the Island) fly by in your little sanctuary. Secluded, yet situated across the street from your own semi-private waterfront beach, beach sounds and ocean smells are abound! Along the mile-long beach, you can swim, sunbathe or take your boat out. Facing West, there are nightly spectacular shows as the sun slips into the water.
    ‘Shelter Island Hideaway’ is on the Eastern End of Long Island, surrounded by Shelter Island Sound and Gardiners Bay, just minutes from the Atlantic Ocean. An 8-minute ferry ride brings you to the center of Greenport on the North Fork and a 3-minute ferry ride to North Haven/Sag Harbor on the South Fork. A third of the Island is a protected area, owned by the Nature Conservatory and known as the Mashomack Preserve. Home to the Itzhak Perlman Music Program, you will find excellent fishing where you can reel in Bass, Bluefish, Snapper and more! Feel free to kayak on calm waters of Crab Creek, steps from the house that connects to the Sound. If you have a jet ski or boat, there is a public launch accessible too, so take a boat out on a cruise or to water skiing! You can rent water equipment at the nearby Water Sports. Just minutes away, limitless sights and destinations will keep you busy during your stay. From cool shops and scrumptious foodie destinations, to antique shops and dozens of wineries, including one named as one of the “Top 25 Tasting Rooms in America” by “Wine Enthusiast,” Bedell Cellars offers picturesque group and walk-in tastings on an outdoor pavilion, located just 12 miles away. Get close to nature at the Mashomack Preserve, with 12 miles of coastline, acres of creeks, woodlands, and fields. The Preserve has 2,039 acres of land offering miles of well-marked trails, dozens of species of birds and animals, Golfers, don’t forget your clubs! Just 3 miles away is The Shelter Island Country Club, a historic establishment that offers a public nine-hole golf course, drinks and dining. For great eats, the choices are endless! Swing by Food Network Featured Vine Street Cafe, or one of Condé Nast top 50 United States restaurants, the Frisky Oyster, or head over to Commander Cody’s Seafood, less than 10 minutes away! You'll always find freshly caught fish, fresh lobster, fried chicken, BBQ and more and BYOB!
    Room Type

    Entire home/apt


    Property Type

    Cottage


    Accommodates

    5


    Bedrooms

    2

    Shelter Island, NY, United States

    Waterfront 2BR, 2BA w/ Pool, Tennis, Docking Slip. Steps to restaurants, bars, shopping. Best location in Greenport. 2 Balconies, Grill, Gorgeous Views, Washer/Dryer, WiFi, 2 TVS, Dedicated Parking Spot.
  • Beautiful home on the water, very clean and stylish. Walking 5 minutes into town

    Adam2019-12-08T00:00:00Z
  • Over Thanksgiving holiday we stayed at Bill's. Super quiet, and crazy weather with 40 mph winds but we stayed toasty. Lots of walking options and so peaceful. 270 degree views and simply stunning. Lots of privacy.

    Clare2019-12-01T00:00:00Z
  • Bill's place is really well located, and the apartment is larger than what you would think looking at photos. Communication went smoothly and the check in/check out process was really seamless. I'm looking forward returning to this stay when in Greenport again.

    Bruno2019-11-11T00:00:00Z
  • We had a great stay! Was an excellent location walking distance to town and a short drive to all of the wineries. Space was open and bright with beautiful water views and large balcony. Everything was sparkling clean. Super responsive communication with host and very accommodating. A perfect place for our weekend getaway. We will be back!

    Kristen2019-11-03T00:00:00Z
  • You can’t ask for a better location or view! Bill was a fantastic host and the place was extremely clean, uncluttered and spacious. The condo community is a quiet enclave right on the water, two blocks from fantastic restaurants, bakeries and shops on Greenport’s main street. Perfect for families. Great beds, strong WiFi and all new smart TVs with OnDemand (no need for your Chromecast!). We didn’t take advantage of the private bbq on the deck or the pool since we were there in the fall, but great amenities for the summer. We will definitely be back!

    Mary Rachelle2019-10-14T00:00:00Z
  • Bill’s condo was absolutely perfect for a weekend getaway. The apartment is incredibly spacious, and well kept— and pet friendly!! We had the most relaxing time laying out on the deck all night until the sun rose right before our eyes over the water. It was truly amazing. The apartment is a 2 block walk to EXACTLY where you want to be in Greenport with plenty of food and drink options. Overall, just a perfect way to spend the weekend!

    Michael2019-06-16T00:00:00Z
  • Bill’s place is terrific, everything you need for a weekend on the North Fork. We loved the small deck overlooking the water for our morning coffee and evening, sunset wine. The location is also very walkable to town which is incredibly convenient. And, Bill is a great host. He was really quick to respond and check in was easy, peasy. We hope to return to Bill’s place soon.

    Dana2019-06-09T00:00:00Z
  • Bill and his home were wonderful! The location is close enough for a quick walk to home but extremely private. We also loved being able to look out from the bedroom and balcony and seeing the water. The rooms themselves were spacious and while there are beds for four, you could comfortably host more than that for dinner, etc. Bill was also extremely responsive and provided great recommendations on what to do while we were there.

    Matt2019-05-18T00:00:00Z
  • Room Type

    Entire home/apt


    Property Type

    Condominium


    Accommodates

    4


    Bedrooms

    2

    Greenport, NY, United States

    Perfect year-round getaway in desirable West Dublin neighborhood of Greenport Village. This 2200 sq ft home is comfortable, spacious, super clean and meticulously landscaped! Sleeps 13 guests comfortably. One of only a handful of homes in the Village of Greenport with a POOL! This home is a perfect location no matter what your interests are out on the North Fork! The fun and relaxation opportunities are endless!
    Take your pick of outdoor areas to relax – on the front porch with views of what’s happening in Greenport Village; on the back deck with a dining set for entertaining, a gas-lined fire pit, a gas-lined grill and an outdoor shower; or in the enormous in-ground pool, or the surrounding lounges chairs and swing. Inside you’ll find a beautiful entry with an open floor plan encompassing the living room, kitchen and dining area. Living room features a gas fireplace, smart TV with cable and a sleeper sofa. The kitchen leads right out to the back deck – perfect for seamless cooking inside and out, and for entertaining! Each floor features a master bedroom with a king bed. Full bathrooms on each floor. Daybed with trundle bed on the second floor living area. Full bed with trundle, and bunk bed set in one upstairs bedroom. Upstairs master bedroom has a smart TV. Steps from Village of Greenport shops, museums, restaurants, breweries, Mitchell Park & the carousel, harbor, piers, roller rink, activities, and much more! Steps down the block you’ll find the bay beach with full jungle gym for kids and full basketball courts. Short distance from famous North Fork wineries, breweries and farms! Convenient ferry ride to Connecticut casinos! Listen to the "Northforker Presents On" Podcast to hear all about what's happening around the North Fork during your stay! The Long Island rail station, the Hampton Jitney, and the Hampton Luxury Liner stops are around the corner – perfect for commuting from NYC or LI. Shelter Island Ferry also around the corner – drive your car right on for access to Shelter Island and the Hamptons. Plenty of taxi services are available for transportation at any time, day or night.
    Steps from Village of Greenport shops, museums, restaurants, breweries, Mitchell Park & the carousel, harbor, piers, roller rink, activities, and much more! Steps down the block you’ll find the bay beach with full jungle gym for kids and full basketball courts. Short distance from famous North Fork wineries, breweries and farms! Convenient ferry ride to Connecticut casinos!
  • It was fantastic! Our first time using Air an& B . Lovely place, great response time. Super helpful thank u!

    Thomas2020-03-16T00:00:00Z
  • This house was a gem in Greenport! The location is ideal with everything is in easy walking distance. The house itself is clean and comfortable and was a great fit for our group. We felt the pictures accurately reflected the space.

    Piper2020-01-02T00:00:00Z
  • Awesome house! Beautiful backyard and outdoor space! Perfect location!

    Gregory2019-11-11T00:00:00Z
  • Great house and fantastic location!

    Elizabeth2019-10-14T00:00:00Z
  • Loved staying at Leah's house! The house and property are so beautiful and the location could not be more perfect. Would highly recommend a stay here, and we'll definitely be back in the future!

    Corey2019-09-30T00:00:00Z
  • Beautiful house in a great location. We stayed with our children and grandchildren for the weekend. Walked to the maritime festival both days and enjoyed the pool! Would definitely recommend and hope to be able to stay again next season!

    Andrea2019-09-22T00:00:00Z
  • We stayed at Leah’s with our in-laws, kids and our dog and everyone had a lovely time. The place is conveniently located right in town, so some people hung out by the pool, while others went shopping and or to the beach. The house was beautiful and clean, I highly recommend!

    Adrianna2019-09-16T00:00:00Z
  • The home is beautifully landscaped, clean, comfortable and in a great location. There is a 24-hour general grocery store 2 min stroll from the house in case you forget anything. The backyard is expansive and the pool lights at night are beautiful. We made good use of the gas fire pit outside, staying cozy with a little wine. Lots of room and great for small groups. Will be high on my list when planning my next visit to Greenport.

    Jose2019-09-02T00:00:00Z
  • Room Type

    Entire home/apt


    Property Type

    House


    Accommodates

    13


    Bedrooms

    3

    Greenport, NY, United States

    Located in the heart of Greenport Village with easy walking access to restaurants, shops, Greenport Brewery, Kontakasta Winery, and much much more! Originally from Greenport, we look forward to hosting you and sharing our local favorites to make your stay memorable.
    Our sunny second floor private apartment in the heart of Greenport features two bedrooms, each with a queen sized bed. The rental was completely renovated this year. The original pine floors were refinished dating back to the early 1900’s. The new custom built kitchen with beautiful granite countertops is fully equipped for your stay. A full sized sleeper sofa is situated in the living room. Full bath with shower and tub. Other amenities include: cable with smart TV, wireless internet, front loader washer/dryer. Linens and towels provided. Parking provided in front of the house. We have beach chairs for your use. This is a non-smoking rental.
    Our beautiful harbor offers many activities including wine tours, kayaking, paddle boarding, hiking trails, antiques, and lots of fantastic restaurants and shopping, just steps out the front door!! The LIRR Train and Hampton Jitney Station is a 10 minute walk (0.5mi), where you will see beautiful views of the harbor. Greenport IGA Grocery Store is 2 blocks away to stock up on groceries for your stay.
  • Perfect weekend getaway! The apt was beautiful, modern and clean. The location was great, quick walk to restaurants and centrally located to stop at wineries or take a trip to Shelter Island. Danielle was great, very fast with responses and check in/out was a breeze. Highly highly recommend!

    Mike2020-03-08T00:00:00Z
  • great space, very convenient location - will stay again!

    Tracey2020-02-17T00:00:00Z
  • Lovely space- all rooms on the upper floor with entrance on the ground level. The living space was bigger than it looks in the photos and very comfortable overall. An easy stroll into the village and two blocks to the playground! We hope to return in warmer weather.

    Andrea2019-12-01T00:00:00Z
  • My friends and I had an amazing trip in Greenport. This apartment is extremely close to town. We felt safe and cozy. Danielle was quick to respond to any questions we had. The apartment is beautiful and extremely clean. I hope to come visit again soon!

    BettyAnne2019-11-24T00:00:00Z
  • Had a great time staying at Danielle’s place for the weekend! Close to town and in close to proximity to the wineries and breweries the North Fork has to offer. Will definitely be back!

    Megan2019-11-10T00:00:00Z
  • Danielle’s place was clean and comfortable. She is an excellent host...gave us lots of information about the area and was very flexible with check in & out times. She was also very quick to respond to all questions.

    Lisa2019-11-03T00:00:00Z
  • Very nice place and good location. Danielle was great and provided many tips on exploring the area. Check in and check out was a seamless process.

    Joe2019-10-27T00:00:00Z
  • Danielle was very responsive! This home is in a great location! Walking distance to great restaurants! Quite street! Perfect for families or a couple looking to get away! We highly recommend staying here!

    Bryana2019-10-20T00:00:00Z
  • Room Type

    Entire home/apt


    Property Type

    Apartment


    Accommodates

    4


    Bedrooms

    2

    Greenport, NY, United States

    Access to endless pool/spa, private beach around corner, breathtaking views, access for kayak, sup etc on property, playful friendly dog, easy access to all including sunset beach, beautiful breeze, private location, 46 foot classic powerboat available for charter at discounted rate w/ rental
    Waterfront charming studio, private location access to 2acres of waterfront property paddle board, kayak, fishing, swimming
    Very quiet and peaceful, adjacent to protected nature preserve, breeze off water keeps pests away
  • John carriage house was a great stay and had convenient access to the water. We enjoyed an evening watching the sunset and playing with the dog.

    Robert2019-10-20T00:00:00Z
  • Beautiful location, nice to have a glass of wine as the sun sets. Room was spacious and Mac (the dog) was so friendly and playful just made the trip a little bit more special.

    Phil2019-09-22T00:00:00Z
  • Great area , beautiful view and lovely grounds ! Would definitely go back and just relax this time and play with John’s awesome dog Mac

    Gloria2019-09-08T00:00:00Z
  • Quiet and beautiful location. Loved the kayaks, pool and sun deck. Would definitely recommend for anyone looking for a quiet weekend on shelter island :)

    Maria2019-08-04T00:00:00Z
  • John was a great host. He was communicative, gracious, and extremely flexible. His guest house looks better than in the pictures. The backyard was fantastic and we enjoyed playing with Mac, his friendly dog. Would highly recommend John as a host and his property for anyone looking for a nice weekend on Shelter Island.

    Samuel2019-07-28T00:00:00Z
  • Staying at John’s is an amazing experience. There is so much to do in Shelter Island. The location is great and unique! John is an amazing host - very easy going and Mac the dog is the most friendly and social dog. He loves to play fetch! :) The room is spacious and clean. John was gracious enough and let us use his kayaks, yard, pool, and fire pit! We had great experience and no doubt will be back! Thanks and cheers John! :)

    Neno2019-07-21T00:00:00Z
  • A wonderful stay. John is a great host. We appreciated the privacy and access to his beautiful property.

    Alana2019-07-06T00:00:00Z
  • My boyfriend and I just spent the weekend at John's place on Shelter Island, for his birthday, and it was amazing!! Everything looks exactly as in his pictures. It's a beautiful and tranquil property and a quick cab ride to get anywhere on the island or to the ferry to Greenport. We especially loved the pool, using the SUP he has available, hanging out on his dock right on the water and Mac -- the friendliest, sweetest dog ever!! John was great and flexible and responsive; really nice to chat with, but also gave us plenty of privacy. We really appreciated the late checkout, as we were able to take advantage of all of Sunday and take the 9pm train back to the city - versus hotels' early checkout times. We will definitely be back!

    Allison2019-06-30T00:00:00Z
  • Room Type

    Entire home/apt


    Property Type

    Guesthouse


    Accommodates

    4


    Bedrooms

    1

    Shelter Island, NY, United States

    Beautifully appointed 1bdrm apt. Farm meets beach chic. Small living room, bedroom, full kitchen & bath. Perfect little getaway space.
    Full apartment is yours for the stay. No restrictions on access to any amenity.
    We are right inside the Village of Greenport...the sleepier side :) You can walk everywhere & anywhere but still get a great nights sleep!
  • We booked this place in the last minute looking for the long weekend. the house is right in the middle of greenport. Sarah was very friendly and house is perfect for two. it was exactly as mentioned in the listing. Thank you.

    Suprabhat2020-02-17T00:00:00Z
  • Great location, friendly staff, will be back!

    Joy2020-02-09T00:00:00Z
  • Perfect location and apartment! Place was perfect and spacious with everything I needed. Also it’s right on top of a fantastic restaurant.

    Noah2020-02-06T00:00:00Z
  • A great place for a weekend stay in Greenport. The location is excellent, right downtown, walking distance to all of our favorite places to eat & drink.

    Daniel2019-12-29T00:00:00Z
  • The place was immaculately clean and cozy and the town is lovely :) there’s a grocery store right across the street and the Main Street/marina just a couple blocks away. We loved our stay!

    Jo2019-11-30T00:00:00Z
  • This was an excellent spot for visiting Greenport. You’re above an excellent restaurant and and a very short walk to the main strips of town. I would stay here again!

    Chris2019-11-17T00:00:00Z
  • Great place, great location, super clean.

    Jason2019-11-11T00:00:00Z
  • Perfect location - walking distance to all the wonderful restaurants/shopping in Greenport, and only a short drive to the many North Fork vineyards and Orient Point Beach. The well-appointed apartment was super comfortable, bright, airy & quiet, as described. Easy checkin and great communication. I hope to return in the Spring for another lovely weekend on the North Fork.

    Carmela2019-11-04T00:00:00Z
  • Room Type

    Entire home/apt


    Property Type

    Apartment


    Accommodates

    2


    Bedrooms

    1

    Greenport, NY, United States

    Rent 1 fabulously cozy room with a queen size bed OR all rooms in this opulent and laid back Victorian home. Super cozy common rooms to lounge and also a relaxing wrap around porch. 127 steps to Main St in the vibrant seaport village of Greenport. 5 minute walk from LIRR train or Hampton Jitney bus station from NYC. 8 miles to Conn. ferry. Free bikes, spacious common areas.. Brewery next door which means growler in the fridge ;).
    Why just rent a room/house when you can have an experience? Ruby’s Cove’s is all about it 's awesome location in the downtown vibrant and walkable seaport village. Great dining, waterside cocktails, beaches, boats, wineries, shopping, art galleries, fun oyster shucking village. Guest become locals in a home base that is both charmingly residential and a frisbee’s throw away from Main Street. Experience what feels like to live in a laid back, elegant, eclectic and welcoming, historic victorian home from the speakeasy prohibition . Only 127 steps to Main Street which means walking distance of both fine dining and casual restaurants, indoor and outdoor cocktail bars, people and boat-watching, antique stores, art galleries, boutiques, a carousel, boat charters, convenience stores, the Shelter Island Ferry, LIRR and the Hampton Jitney. A 5 minute walk (or free pickup) from the train or bus from NYC. And for you beer lovers, the newly opened Greenport Harbor Brewing Co. is literally in the backyard! Whew! And as if that’s not enough, Ruby's Cove is only a short drive to over 50 wineries, gorgeous white sand and rocky beaches, and parks, farm stands and the Cross Sound Ferry. Bicycles are included with your stay and this area is spectacular for cruising around and exploring. That’s how I fell in love with this vibrant and whimsical town and we would like to share that with you. Stay at a top rated by trip advisor/YELP B&B in the wine country of LI, NY. For questions, inquiries or delightful conversation please contact me by message or phone call. Always a growler of brew from next door and some wine waiting for your arrival. **We offer individual rooms for the rate listed and full house rentals , Special accommodations, group rentals, parties always considered.
    Ruby's Cove is in the Historic District in Downtown area. A little dock at the end of the block where you can jump off and swim in the bay. Greenport Harbor Brewing CO. right next door.
  • Such a great spot! The house is clean, comfortable and in the perfect location - walking distance from the water, restaurants, and shops and a quick bike ride (which are provided) to the nearest vineyard. Donna was a great host and provided us with all the insider tips on where to visit while we were in town. I highly recommend it!

    Keith2018-08-26T00:00:00Z
  • Donna is great. She is very helpful and easy going to help your stay be relaxing and comfortable. Her B & B is one block from water and town. Everything at your fingertips

    Christina2018-08-02T00:00:00Z
  • The place is amazing, Donna was an awesome host!!

    Louis2018-07-15T00:00:00Z
  • Had a wonderful stay at Ruby’s. The location does not get any better...literally right in town. The space is eclectic but not stuffy whatsoever. Also had the pleasure of sharing stories with Donna on the porch. Looking forward to coming back.

    Matthew2018-06-27T00:00:00Z
  • Donna is an absolutely wonderful host. She is thoughtful and communicative and very friendly. It was really a pleasure to stay in her home which was in just about the best location in Greenport. Walkable to everything and with bikes that you can borrow at any time. Would definitely recommend this stay to a friend.

    Emily2018-06-26T00:00:00Z
  • Wonderful and quaint Victorian house to stay in, Donna is a wonderful host and rock of the community, knows the best places, we will be back.

    Matthew2018-06-21T00:00:00Z
  • Donna was wonderful and super helpful host. She gave us lots of great tips on food bike rides etc.. We enjoyed our stay tremendously! Such a great getaway from the city!

    Nico2017-08-17T00:00:00Z
  • Donna and her house were wonderful. Great location and Donna was so accommodating. Best part was the beautiful sitting rooms where you can sit and relax. Also loved Donna's bikes. We used them to ride to the wineries. Great stay and host.

    Chris2017-08-04T00:00:00Z
  • Room Type

    Private room


    Property Type

    House


    Accommodates

    2


    Bedrooms

    1

    Greenport, NY, United States

    Born from the name of the 75-year-old tree in the center of Greenport Village’s historic Stirling Square, this former 19th-century horse stable has been converted to American Beech Restaurant, Bar & Hotel—an updated destination for unpretentious dining and dwelling, stimulated by the vibrant North Fork region of New York. The boutique hotel features eleven Suites, including two two-bedroom apartments. The Suites combine a tropical decor with original art available for purchase from VSOP gallery.
    Each of our rooms come with a fully stocked mini-bar, Nespresso machine, Smart TV, glass shower door, iron, ironing board, hairdryer and Maison Margiela amenities. We've also included robes, Frette beach towels, complimentary yogurt & granola, and coffee pods to make your stay all the more memorable!
    American Beech Hotel's special location in downtown Greenport is walking distance from the Peconic Bay shoreline, and a bike ride from beaches on the Long Island Sound. Hotel guests have access to complimentary bike rentals and Greenport is home to a diverse collection of local businesses, including shops, cafes, restaurants and bars. The North Fork of Long Island's agricultural and aquatic landscape provides delicious ingredients for our many culinary destinations. Our local seafood is always fresh and each season here offers a variety of local activities.
  • American Beech is everything you want on a getaway. Beautiful rooms, amazing hospitality, food and the views. Everything is within walking distance and parking was easy and free! Very safe and beautiful area. No complaints at all! Can’t wait to go back.

    Alyssa2019-10-01T00:00:00Z
  • Room Type

    Private room


    Property Type

    Boutique hotel


    Accommodates

    4


    Bedrooms

    1

    Greenport, NY, United States

    Explore the charming seaside village of Greenport from this quaint 1-bedroom, 1-bathroom vacation rental apartment with sleeping accommodations for 2. Only a couple of blocks from downtown, enjoy quick access to numerous restaurants, boutique shops and local attractions. Your ultimate North Fork adventure awaits you in this incredible apartment!
    Bedroom: Queen Bed Enter into this lovely charming apartment through a warm and inviting living room where you and your guests can relax and recharge. The space features a comfortable leather sofa along with a flat-screen smart TV with Netflix and streaming capabilities. Adjacent to the living room is a fully equipped kitchen that includes all your basic appliances and a breakfast bar with seating for 2. The bedroom lies off the main living area and is tastefully decorated in cool tones and beach-themed wall art. Need a breath of fresh air? Enjoy access to a private porch on the side of the house that includes 2 wicker chairs and a small glass table.
    Enjoy the convenience of being only a short distance from downtown along with the peace and quiet away from the hustle and bustle. Located only 2 blocks from Main Street and 3 blocks from Front Street, head downtown for a day of fine dining and shopping. When you’re through exploring the village, hop a ferry to Shelter Island, a unique island community with country charm. For a day on the water, Sterling Creek is only a short distance down the street. Head down to the dock and watch the boating activity in Greenport Harbor or go for a swim in the cool water.
  • A really nice apartment. So close to the village. Easy walk to town.

    Craig2019-10-06T00:00:00Z
  • Great location!!! Close to everything you need and want. We walked into town each morning and night. Also very close drive to wineries and trails. It was very clean and well equipped. Would definitely recommend. :)

    Corrinne2019-09-30T00:00:00Z
  • This apartment was in a perfect location, close to anything you would want to do. There were local tips provided in a book about restaurants, beaches, and driving services. I would definitely recommend this apartment to anyone visiting Greenport for a getaway!

    Brianna2019-08-31T00:00:00Z
  • Great place! Apartment was very clean & location was amazing. Got locked out 1 night and were able to get it resolved with Evolve in a mater of minutes. Awesome service!

    Amy2019-08-25T00:00:00Z
  • A second story apartment a couple of blocks away from Main Rd in Greenport. Check in and check out instructions were easy to follow. The apartment was very clean and welcoming, with a guest book and local information. Loved the idea to have a small stock of beer which is replenished by guests so there is a nice selection.

    Michele2019-06-03T00:00:00Z
  • John was great, the place was perfect. We are planning when we can come back.

    Chris2019-05-19T00:00:00Z
  • The home was quite quaint and perfect for our weekend in Greenport. It was an easy walk to Main Street or the Shelter Island ferry. It was an easy drive to many of the wineries. The closest winery, Kontokosta, is a 5 minute drive away and has beautiful grounds to walk on and sip some wine. The description was exactly what I expected and the host left a binder with instructions and tips for our visit. I wish I would have had the chance to sit on the front porch but maybe on the next visit!

    Carmen2019-04-28T00:00:00Z
  • Perfect space close to everything in Greenport. Clean, cozy, and easy to access, this home is walking distance from the main strip in Greenport. Also a short drive to wineries, breweries, and some nice hikes. Definitely recommend.

    Michael2019-03-17T00:00:00Z
  • Room Type

    Entire home/apt


    Property Type

    Apartment


    Accommodates

    2


    Bedrooms

    1

    Greenport, NY, United States

    14 night minimum $150/night March through April. Great WiFi! Fab kitchen 4BR restored 1960s ranch with a breezy nautical theme. Giant deck: Propane & charcoal BBQ, Jacuzzi, Teak Deck Chairs, Hammock & Outdoor Shower. private front & back yards. Fab mirrored bar, renovated kitchen, double-sink master bath+full second bth. Impressive vinyl collection, piano, basement media room with bench press & ping pong! washer/dryer. 2 bikes (can rent more).
    Note: Jacuzzi is closed 12/1 thru 4/15. Sleeps up to 8 adults plus extra mattress fit in bedrooms for children. Home has a fun 1970s-inspired nautical look. Gorgeous light hardwood restored parquet floors and wood paneling throughout. Lots to do rain or shine and home was gut renovated and very well appointed. Bathrooms have 12 large white bath towels and 12 colorful beach towels. White robes also provided. All bedrooms have cozy duvets. The kitchen, which opens into the living dining room, is well stocked for the chef and baker in your group! Bar is complete with wine glasses, cocktail shaker and glasses, glass punch bowl, etc. Re Games -- Football, Tennis Rackets (courts near by), Badminton, Frisbee. - all for you to use. Relax on teak deck chairs, snooze on the hammock, take an outdoor shower or soak in the Jacuzzi. Indoors, besides listening to records or your iPhone music on the stereo, you can play piano and various percussion instruments, Ping Pong, Playing Cards, Chess, Scrabble, Trivial Pursuit (2 editions!), Risk, Othello, etc. In addition, the retro basement media room has 4 speakers, another record player, and a flat screen TV with Netflix, Hulu, Amazon Prime or YouTube. There is also a weight room just make sure to wear shoes! Ceiling fans in all bedrooms except Cabin 4 which has a floor fan. A/C mini splits in living room, basement media room, and cabins 2 and 3. Home is cheery with lots of sunlight during the day through fabulous jalousie windows and feels very chill in the evening with soft lighting throughout on dimmers. Close to Hay Beach&Coecles Harbor. Walk to tennis+miniature golf. Central air. Rental ID# 19-S-0022
    Quiet. Very few cars on road. Lots of deer and turkeys. Bucolic.
  • Great and cozy weekend getaway! Great location on the island, glorious fall foliage.

    Lesley2019-11-11T00:00:00Z
  • Isaac is a great host and this is a hidden gem of an airbnb. We have a toddler and a baby and it worked out great! 5 minute drive to everything on the island. Hot tub was clean and easy to use. So cool to look at the stars through trees while you relax. The back porch and yard are beautiful. The living room is just a gem with windows all around it has the bucolic feel us city folk needed. Listen to records and enjoy your family and friends company. Love.

    Stephanie Jo2019-08-06T00:00:00Z
  • We had a great weekend stay in this lovely Shelter Island Home. Unique and attentive decor made this a memorable stay. Would recommend staying here if you are looking for calm, quiet, and serene.

    Patrick2019-07-30T00:00:00Z
  • Nice clean space in a good location on Shelter Island. Isaac communicated well before we arrived, and we were happy with our visit!

    Ahmed2019-06-30T00:00:00Z
  • Great record collection

    William2019-06-16T00:00:00Z
  • This home is beautiful! Isaac has created a mid century modern masterpiece and we absolutely loved it. We used the hot tub every night and it was the perfect end to each day. Highly recommend!

    Nico2019-06-09T00:00:00Z
  • Excellent stay all around

    Bj2019-05-19T00:00:00Z
  • We really enjoyed our stay at Isaac’s place! We loved relaxing in the hot tub and enjoying his large collection of records. We’d definitely recommend this place!

    Hannah2019-04-28T00:00:00Z
  • Room Type

    Entire home/apt


    Property Type

    House


    Accommodates

    8


    Bedrooms

    4

    Shelter Island, NY, United States

    Play. Sip. Stay. Welcome to the Guest House and sister hotel of Matchbook Distilling Co. Here you can find the traditional vineyard and beach resort reimagined into a guest house, where creativity, relaxation and indulgence can all be found in equal measure.
    Five oversized guest rooms with en suite bathrooms are each available to rent throughout the year. Rooms may include clawfoot bathtubs and balconies that overlook the garden, barn and neighboring Kontokosta Winery. Rooms are check yourself in and out with keypads that allow you to immerse and emerge yourself at your total convenience. We’re delighted to host guests aged 21 and over.
    The Lin Beach House is surrounded by pebble beaches and 54 wineries. In addition, you're just a walk away from downtown Greenport - which is home to a great food and beverage scene as well as some shopping.
  • The space was beautiful and we can’t wait to come back during the summer. A perfect place for our anniversary! The bar downstairs was super cute and would be a perfect place for a shower or engagement party!

    Elise2020-03-07T00:00:00Z
  • Instragram worthy interiors!

    Toni2020-03-02T00:00:00Z
  • Amazing space with gorgeous views! Very close to the main town, maybe a 15 minute walk. Very quiet at night and feels extremely private for a hotel style place. Already planning to come back!

    Bobbie2020-02-17T00:00:00Z
  • The Lin Beach House was a wonderful stay! Leslie was prompt in answering my questions and gave great restaurant recommendations. The Bianca room had very nice touches and was a super cozy suite that is a lot bigger than you would have thought. Best part of the room was the amazing, huge shower with 4 jets! We were only there for one night but it was very relaxing for a winter stay in Greenport. Would definitely come back in the summer time!

    Melissa2020-02-16T00:00:00Z
  • Spacious and clean rooms...close to village of Greenport... private parking... next door to Kontacosta winery too!

    Chris2020-02-09T00:00:00Z
  • Great place to stay in Greenport!

    Alan2020-02-02T00:00:00Z
  • Great space

    Emily2020-01-23T00:00:00Z
  • Bianca’s room at Lin’s Beach House was lovely. The room and shower were huge and beautifully decorated. Pictures are accurate, room was very quiet, check-in was the easiest and the hotel overall was gorgeous. We didn’t get a chance to enjoy the bar as it is closed on Sundays, so we’ll have to come back for that. Note to travelers without cars: the house is about a 30 minute walk from the train station and port area where most of the restaurants and bars are, but getting an Uber is no issue. We really enjoyed our quick trip and look forward to returning to Greenport and Lin’s.

    Johanna2020-01-20T00:00:00Z
  • Room Type

    Hotel room


    Property Type

    Boutique hotel


    Accommodates

    2


    Bedrooms

    1

    Greenport, NY, United States

    A room in our Bed and Breakfast with a queen size bed and a shared bath. Five quest rooms share two baths. Continental breakfast included in the downstairs lounge. Second story deck for the quests to use.
    Season rates: $106 on weekdays Weekend rate is $106 to $129/night, with a 2 or 3 night minimum on season. Minimum stay requirements vary between seasons. Off season rates vary. Shelter Island is nestled between the two Forks (South Fork, the Hamptons) and the North Fork. Island is ideal for vacationing, just a quick trip from NYC, but a world away. Beautiful beaches, nature walks, biking, kayaking... also fine dining and nightlife.
  • I have never experienced staying in a shared home before, but it turned out much better than what I was expecting. It was nice to see how clean the place was kept and the taxi service was very convenient. I would recommend anybody looking for a place to stay at Anu's place.

    James2019-09-29T00:00:00Z
  • Well situated for access to Wades Beach, Anu’s place is quiet and tranquil, great if you are looking for wedding-weekend accommodation!

    Samuel2019-09-08T00:00:00Z
  • Easy check in...and out. Very clean and close to everything. Can’t beat it for the price.

    Jennifer2019-08-26T00:00:00Z
  • You know it doesn't matter if it's a hotel, a B & B or a tent...clean is clean is clean...Anu's place is very clean and I really appreciate that...I had no problem sleeping and the coffee with half/half was excellent...place was a perfect fit for me and what I needed to accomplish.

    Anne2019-08-24T00:00:00Z
  • Anu's place in clean and affordable and the breakfast was a nice touch.

    David2019-08-13T00:00:00Z
  • Great location, easy booking and check-in. Overall a very nice experience. Thanks!

    Mary2019-08-08T00:00:00Z
  • GREAT value and location. Easily accessible. Great parking.

    Megan2019-07-28T00:00:00Z
  • Great place for a one night getaway!

    Steph2019-07-21T00:00:00Z
  • Room Type

    Private room


    Property Type

    Bed and breakfast


    Accommodates

    2


    Bedrooms

    1

    Shelter Island, NY, United States

    Play. Sip. Stay. Welcome to the Guest House and sister hotel of Matchbook Distilling Co. Here you can find the traditional vineyard and beach resort reimagined into a guest house, where creativity, relaxation and indulgence can all be found in equal measure.
    Five oversized guest rooms with en suite bathrooms are each available to rent throughout the year. Rooms may include clawfoot bathtubs and balconies that overlook the garden, barn and neighboring Kontokosta Winery. Downstairs you can find Days Like These, Matchbook Distilling Co.’s bar and tasting room, open Tuesday - Saturday. We’ll offer serve-yourself coffee & tea during the day and we’ll open for cocktails at 5pm. Rooms are check yourself in and out with keypads that allow you to immerse and emerge yourself at your total convenience. We’re delighted to host guests aged 21 and over.
    The Lin Beach House is surrounded by pebble beaches and 54 wineries. In addition, you're just a walk away from downtown Greenport - which is home to a great food and beverage scene as well as some shopping.
  • Great place! Eclectic and perfect location. The beach is amazing and really is within walking distance! Plenty of nearby restaurants/ bars. There is a “hidden” tasting room that is worth a visit even if you’re not staying there. Enjoy!

    Irv2020-02-17T00:00:00Z
  • The Lin Beach house was a great spot for a weekend getaway. Very close to downtown and walking distance to a winery behind the place. Will definitely be back!

    Gregory2020-02-16T00:00:00Z
  • We had a really lovely time staying here. Check-in was seamless and the bartenders were really helpful and hospitable. Room was sparse but nice. Bathroom is huge. A few quirks about the Jane Suite: 1. It’s right above the bar area so expect to hear music and voices in your room until about midnight. 2. The room gets really bright in the morning at sunrise. Those sensitive to light should be aware. 3. The room faces the Main Street. Not a big deal for us but some might care.

    Kho2020-02-09T00:00:00Z
  • So nice we booked it again for next month

    Christopher2020-01-26T00:00:00Z
  • The Lin Beach House is a true treasure and hidden gem on the north fork. Gorgeous rooms, the bar downstairs is beautiful and the bartenders were very kind. Coffee station in the morning was great too!

    Lauren2020-01-11T00:00:00Z
  • My husband and I loved Leslie’s place. Our room was stylish and the bed was very comfortable. Also, the bar downstairs is perfect for a nightcap or to get your evening started. Delicious and creative cocktails. Overall a wonderful stay. Highly recommend.

    Jocelyn2020-01-01T00:00:00Z
  • Loved staying here. Very large and clean rooms, easy check in process and about 1 mile to the village center where there are plenty of bars and restaurants. The bar downstairs was really nice and had a vintage feel to it. Excellent cocktails. Didnt try any food here, so cant really comment, but it sound like everything was amazing. Will definitely come back here. I'd highly recommend staying here

    Jaydev2019-12-15T00:00:00Z
  • nice simple and clean

    Rosario2019-12-14T00:00:00Z
  • Room Type

    Hotel room


    Property Type

    Boutique hotel


    Accommodates

    2


    Bedrooms

    1

    Greenport, NY, United States

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