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1000+ Rentals · Southold
1000+ Rentals · Southold
Sunny, large, 2,000 square feet, beautiful and spacious 4 bedroom second floor apartment in the HEART of downtown Greenport! Located on Main Street steps from the water! Everything inside this apartment is BRAND NEW! Experience a modern, hip feel in a historic, classic Greenport building! Enjoy beautiful Marina, Mitchell Park and Shelter Island views from the kitchen and bathroom! This recently upgraded early 20th Century building is full of charm. Steps from Noah's, Scrimshaw,The Frisky O...
In the Heart of picturesque Greenport and on a quiet and leafy block, this 2 Bedroom renovated apartment in a 2 family home offers an ideal retreat. There is a large living space and kitchen, a sunny deck with views and bedrooms at opposite sides. Learn More
A charming first floor apartment with a large, fully equipped, eat in kitchen , a large deck with views of the garden and a partial view of the marina. There is also a small enclosed porch where one can sit and relax with a cup of coffee in the morning. The living area is large enough for a dining room table and the two bedrooms are both spacious and on opposite sides of the apartment. There is a private deck off the kitchen with a small table and four chairs. The property is ideally l...
Available for a min 3 nights:This is the grnd fl of a 3 family vacation rental home. Perfect place to relax after the wineries, galleries, beach, boating and shopping. Easy 2 blk walk to all Greenport has to offer, yet far enough away to be quiet! Learn More
This is the entire ground floor of my 3 family vacation rental home. I live 4 doors down the street so I am always available. You enter thru the front door. The shared common foyer is for you and the upstairs front apartment guest. The first door on the right is the entrance to your apartment. You have digital keypad lock on the doors so no keys to play with. I am a local here so any question about anything to do, go,see, etc I can help and would be happy to do so...I love to share th...
Enjoy a spectacular view from the living room that extends to the gorgeous new saltwater gunite pool with spa. Beautifully decorated, comfortable home. Chef's kitchen and fabulous restaurants within minutes. Wineries, farms, beaches and exquisite small towns all nearby. Simply put, a peaceful paradise for you and your group. Learn More
Beautifully decorated, spectacular view, new saltwater gunite pool, new outdoor shower, cable, HD tvs, wi fi, DVD player, Apple TV, propane fireplace, BBQ grill, gourmet kitchen Pool, 1 acre of property, large driveway As often as they wish Peaceful beautiful wine country, nearby beaches, dining and shopping in several close by towns. Hampton Jitney bus stop is 3 minutes away, great for getting to or from New York City. This is beautiful property that really must be seen in person. Loo...
Second floor apartment overlooking Greenport Harbor and Front Street on the beautiful North Fork of Long Island. In walking distance to all the action. Live music at Claudio's Clam Bar, dining at top notch restaurants like The Frisky Oyster, Biere, and Noah's Restaurant. Stroll to Aldo's for your morning cup of coffee and relax in Mitchell Park Marina and ride Greenport's own carousel. Walk to Greenport Brewery for local art, music and Greenports finest brew! Walking distance from the Jitn...
Long Island Wine Country, Pumpkin & Christmas Tree Farms, Beaches, Boating, Shopping, Cafe's, Art Galleries, Biking, Night Life, Dancing, Tours, Fishing, Boutiques, Ice Cream Shops, Famous Carousel, Dockside Dining & Entertainment, Ice Rink Learn More
Second floor apartment in the heart of the Greenport Village where all the action takes place! Walking distance to top rated restaurants, clam bars, art galleries, boating, beaches, swimming, biking, Greenport’s own carousel, brewery, tea and coffee cafes, live music, dancing, night life, ice cream shops, boutiques, grocery shopping, farmers market, local farm stands, tour rides, and wine tasting! A short distance from several local seafood markets. Something for people of all ages! This...
Charming, sunny 2,300 sq. foot home in a quiet corner of downtown Greenport. This 1890's house has 4 bedrooms, 2 bathrooms and an eat-in kitchen overlooking a large, gracious fenced in yard. Just steps away from Greenport's finest! Family friendly!!! Learn More
Starting June 22, we will be requiring a 5 night stay for the rest of the summer. May be able to make certain accommodations for mid-weeks and therefore have a few weekends available. Always ask! :) Charming, sunny and spacious 2,300 sq. foot home with 4 bedrooms and a gorgeous yard in a quiet corner of downtown Greenport. Built in 1890, this home features impeccable hard wood floors, beautiful tin ceilings and walls and an adorable window seat- all within steps of Greenport’s finest. This...
Well located Greenport 2 family home. Both homes accommodate 12 adults. total 5 bedrooms, 4 baths, 2 newly renovated kitchens, 2 laundry. VERY large open kitchen, living room, sunroom and dining room spaces. BBQ and large yard. Learn More
Newly renovated 2 family in the heart of Greenport Village. A perfect space for a family vacation or a group getaway. All bedrooms have new beds and bathrooms are recently renovated. Very large open kitchen, sunroom, living room and dining room is perfect for entertaining. Large patio and backyard as well as outdoor shower. One home has 3 beds, 2 baths as well as a queen sleeper and the second duplex on 3rd and 4th floors offers a separate living space with 2 beds, 2 baths. Each house can ...
Private bungalow, with a separate entrance, in a historical tudor home with spacious bedroom, kitchen and bathroom. Walking distance to beach, restaurants, shopping, vineyard, farm & fish markets. Jitney stop within a block, bikes, Apple TV, internet & private parking all provided. Perfect NoFo getaway! Learn More
Private bungalow in a beautiful historic home with private entrance - the space is completely separate from the main home. Bedroom with queen-sized bed includes internet and television with Apple TV. Sweet kitchenette with table & chairs, refrigerator, freezer, microwave, coffee maker and sink. There is a full private bathroom with tub & shower, sink and toilet. All fresh linens, towels and complimentary snacks and water included. Access from the private entrance on the Main Road in Cutch...
Fabulously cozy room in a laid back Victorian home 127 steps to Main St in the vibrant seaport village of Greenport. Enjoy the rest of the house including wraparound porch, spacious common areas and free bikes. Brewery next door. group rentals too. Learn More
Why just rent a room when you can have an experience? Ruby’s Cove’s is all about it 's awesome location in the downtown vibrant and walkable seaport, great dining, shopping, art galleried, 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...
New house with private beach access and a 5-min drive to historic downtown. This 4 bed, 4 bath sleeps up to 10 and features two masters. Large common areas for cooking, eating and vegging out with a 55" flatscreen. Large yard for BBQs and relaxing. You'll love your stay! Learn More
The house is in a nice beach community neighborhood with great access to town and recreation. Plenty of parking at the house. Manhattan to downtown Greenport via Hamptons Jitney and LIRR. Details: - Private access to neighborhood beach 3 blocks away - Beach towels - Bath towels - Iron - Ceiling fans in all bedrooms - Pull-out sofa in den area (sleeps 2) - King-size beds in master bedrooms (2) - WiFi - Wireless keypad entry - Fully equipped kitchen - 55" TV - Games - Washer/dryer - Charco...
This beautiful, one-of-a-kind beach house is located on 4 acres with a private beach spanning 1,100' on either side of the Greenport Jetty. The property faces the spectacular view of Shelter Island and the Peconic Bay and Greenport Harbor. Learn More
This beautiful, one-of-a-kind beach house is located on 4 acres with a private beach spanning 1,100' on either side of the Greenport Jetty. The property faces the spectacular view of Shelter Island and the Peconic Bay (to the East) and Greenport Harbor (to the South). Breakwater Cottage offers a beautiful outdoor lawn and panoramic water views from every room in the house that are enhanced by the evening sunsets. Breakwater was completely renovated in 2006 and features a fully equipped ...
Walk from the Jitney to this cute Victorian home in Greenport. Car is optional! Steps to the beach, harbor, coffee shops, restaurants, bars, and vintage carousel. Private patio and garden, Central AC, Laundry, Full kitchen, WI-Fi & Bose. Learn More
Relaxing, comfortable B&B in the heart of the North Fork. Enjoy the vineyards, beaches and farms and revive in a cozy little farmhouse. The Florentine room offers a soft Queen bed with own private bathroom. Learn More
Newly renovated room with en suite bathroom. Sip coffee on the front porch. Kick back on the back deck and enjoy the views of the North Fork Country Club golf course. Common areas are available to stretch out and meet the other guests. Wanna find something fun to do? We're here to help you make the most of your stay. Cutchogue is in the heart of the North Fork. It is know as the "sunniest" place in New York. The Hampton Jitney is walking distance away. Drive in or rent a car to get the...
Lovely 1890's farmhouse located conviently in historic Greenport Village. Take a 3 minute walk into town and enjoy the best restaurants, art galleries and shopping. Newly renovated kitchen with stainless steel appliances and custom cabinetry. Learn More
2 full queen size beds up stairs with full bathroom. Downstairs, beautiful open living room with original wide planked hardwood floors and .5 bathroom. The kitchen is a chefs dream with state of the art appliances and work space. Outside, huge lawn, full bbq and gorgeous cedar planked dining table for grilling your catch of the day. End your day in one of the 2 rocking chairs on the front porch. Guests will have access to entire house and backyard. We check all guests in. There is a...
Built in 1828 for a ship’s captain, this historic property remains as one of the oldest structures in the village. Original details abound. Large, bright & airy rooms. Brand new furnishings. Learn More
Located on a tree lined street this sun-filled two story house sleeps up to 9 people. It features 3 bedrooms, 2 full bathrooms, a large eat in-kitchen, a lounge room with a queen size sleeper couch and a spacious living area with TV and wifi. The private fenced-in backyard offers plenty of space to unwind with a covered porch, BBQ facilities, deck chairs and a brick enclosed fire pit. Steps away from Greenport Village and walking distance to restaurants, cafes, Greenport Brewery, the Shel...
Explore Long Island Wine country. Peaceful, private, relaxing, comfortable, super clean and spacious studio apt. with private bath, private balcony, close to all. Walk to vineyard, bike to beach. Learn More
Huge, modern, eco friendly guest studio suite in luxury private home. Self contained with separate entrance, private bathroom and private outdoor terrace with woodland views. We provide quality linens and towels, including European duvet with linen covers, freshly laundered between guests, not blankets. The suite has CAC (central air conditioning) as well as ceiling fans, and is fully heated with its own thermostatic controls. There is a 36" LCD TV, no Cable TV, but media player with Netf...
This charming schoolhouse, built in the 1880's, has an open floor plan, and is perfect for relaxing and entertaining. The house was updated in 2013, so has all of the modern amenities amidst the old world charm. Learn More
The Old Schoolhouse tells a family story, dating back to the 1880's. Although the house is old, it was moved and a new foundation was built in the 1940's to support the structure. The prior owners updated the house in 2005 with the most energy efficient systems, so the charm is intact, but the house is supported by a modern infrastructure. This house has an open floor plan and the light is bright. Perfect place to hang out and relax, cook, read and just enjoy. The three bedrooms are q...
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