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1000+ Rentals · Southold
1000+ Rentals · Southold
This historic Captain's house dates back to 1830 making it one of the oldest houses in Greenport. It has been beautifully renovated preserving the historic detail. It has a huge garden with mature trees, plants and a wonderful gazebo. Learn More
This is the garden wing of a beautifully renovated historic Greenport house dating back to 1830. It's one of the oldest in the Village of Greenport. The garden wing offers 2 bedrooms both with queen beds. One is next to the cozy living room on the ground floor. The second one is on the second floor off the big eat in kitchen with its vaulted ceiling. The garden wing is abundant with historic details, most notably the impressed tin ceilings and walls in the living room and first floor bedro...
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...
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...
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 ...
Walking distance to Micari Vineyards, among others, and the Village of Cutchogue, this cottage is a perfect getaway with great proximity to all that the North Fork has to offer. It is set back behind the main house with lots of space between. Learn More
My one bedroom cottage has the living room open to the kitchen area (with brand new stove and refridgerator), hardwood floors, full bathroom, all newly renovated. There is an air conditioner in the bedroom and ceiling fan in the living roomThe Cottage sits in the back of my property so you have privacy and your own outdoor space. It is truly quiet and peaceful. The only sounds are birds chirping.. And if you are going to a wedding I am minutes away from many Wineries!! I will be home for ...
Refined, contemporary style awaits you in the heart of wine country, just steps away from six local wineries. Newly renovated 1921 home features boutique style gust rooms with private baths, modern amenities and complimentary Wi-Fi. Learn More
Our newly designed guest rooms are equipped with organic toiletries, hair dryers and turkish cotton towels. To truly experience the North Fork, we intentionally keep our rooms clean and simple, without Televisions. Complimentary Wi-Fi is always available and Central Air is included from May through September. Common space includes: Dining & living area, front and side porch as well as backyard patio. For your safety Kitchen is private, we’re happy to keep items in the refrigerator for our...
Nestled in the heart of the North Fork this chic Cutchogue farm house is comfortable and spacious. It sleeps up to 9 adults with it's 4 large bedrooms. The guest bathroom has been renovated and features a reclaimed barn wood vanity and marble shower. The chefs kitchen was also recently remodeled and has a 5 burner gas range and wine fridge. But you won't just fall in love with the inside. The yard provides 2 very private acres, with a refurbished horse barn for outdoor entertaining. Learn More
Take it easy in the Over Easy Room!!! Sleep in a comfy bed and relax in your private pedestal tub. Recharge for the adventures that await on the North Fork... Learn More
A truly one of a kind B&B offers a great place to stay and and awesome breakfast to start your day. Sit back and watch the world go by on the front porch or relax on the back deck. There are many guest areas both inside and out to relax and enjoy. Wanna know what's around. We're here to help you make the best of your stay. Cutchogue is known as the "sunniest place" in New York. Come see the local wineries, beaches and farms. There's a little bit of everything. Feel like shopping? Check...
Gateway to Oregon Road's, Sophisticated Designer's Retro Art drenched 2 Bedroom, 1.5 bath ranch w/ porch on 1.5 acres borders farmland from the front yard, a tree farm from the back yard & vineyard. Ideal for couples or families. Child friendly! Learn More
Chic, ecclectic and comfortably designed for easy living on one floor with designer and retro details makes this home a perfect central location to explore the North Fork's beaches, vineyards, villages and nature or have a getaway. The house sleeps 6 with the Queen sleeper couch in the living room. Ideally two couples with a guest can sleep comfortably or a family of four for shorter stays. For longer stays, a family of three with an occasional guest. Whether a couple, couples or for a...
Beautiful bright Greenport village duplex in legal 2 family home. Large eat in kitchen, living room, 2 large bedrooms and bathrooms, laundry room. Max 4 people. 2 night minimum for weekend stays. No AC but good air flow and fans Learn More
Beautiful 19th century duplex in legal 2 family home Entire house. Front entrance to the house very private We have a caretaker on the premises Walking distance to restaurants and shops. Less than .75 mile from the nearest winery. 10-15 minute walk from the bus stop and train. The train is next to the ferry Since this is a 2 family there could be another renter in the other home. The homes are separate but both homes have the original plank flooring so its possible to hear one another ...
As part of the strip of historic homes along Main Road in Cutchogue village , this tastefully restored antique cape offers all the charm you seek of a North Fork home with many added conveniences of the village location. Learn More
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...
Our adorable 2 BR cottage in the heart of wine country in LI's North Shore is impeccably decorated with a separate breezy, sunny dinning room and screened in porch. We are less than 1/2 mile walking distance to two beaches or less via our kayak! Wifi Learn More
Charming beach house, impeccably decorated yet still homey, warm and comforting, Kitchen, bath redone; sun room with windows open; rarely need A/C. Close to the beach (1/2 mile), closer to water access for kayak (200 yards), wineries and great restaurants! Just added a Tempurpedic mattress in the master bedroom! Enjoy our beer garden porch! House has a storage attic that is not included. I our garage, find Kayak, bicycles, gas grill, fire pit all included! You have free reign to everything...
Beautiful summer rental available on Long Island’s North Fork. Three-bedroom cottage located in Cutchogue, NY. -The heart of wine country -Sleeps six to eight -Indoor and outdoor showers -One block from lifeguard-protected beach Learn More
Beautiful summer rental available on Long Island’s unspoiled North Fork. Three-bedroom cottage located in Cutchogue, New York, in the heart of wine country; sleeps six to eight; indoor and outdoor showers. The cottage is one block from a lifeguard-protected beach on Little Peconic Bay. Local attractions include swimming, fishing, boating, kayaking, numerous wineries, fruit and vegetable farms, outlet shopping (one half-hour away), Splish-Splash water park (one half hour away), the fishin...
This newly renovated cottage has a spacious living room, large eat-in-kitchen, 2 bedrooms; one with queen-sized bed, the other with two twins, and one full and one half bath. Learn More
This newly renovated cottage has a spacious living room, large eat-in-kitchen, 2 bedrooms; one with queen-sized bed, the other with two twins, and one full and one half bath. There is a waterview across the street from the relaxing 'pebble lounge' the garden seating area in front of the house. There are a/c units in the bedrooms and living room. The house is located in the middle of wine country and 5 minutes by car from Cutchogue beach on Pequash Ave., off the Main Road, with small park, p...
Charming 3br/2ba farmhouse with porch heart of North Fork wine country. Bike to Peconic Bay life guarded sand beach beautiful Cutchogue Harbor. Greenport & Shelter Island, favorite summer destinations, nearby. Hamptons ocean beach half hour drive. Learn More
Cutchogue is said to be the sunniest town in NYS. House sleeps 8 (king bed, 3 twins, trundle under twin & pull out full size sofa bed). Central AC, fully equipped kitchen, laundry, piano, board games, Wii, Xbox, cable TV, movies, internet, patio furniture, fire pit, gas grill, charcoal grill and outdoor ping pong table. Bedrooms are upstairs. Bathroom on first floor has a bathtub. Basement bathroom has a sit down shower. There's also an outdoor shower. Laundry is in the basement. ...
Newly renovated beach cottage - less than 10 min to 10+ wineries! Near great beaches, fabulous restaurants, farm stands, golf, boating, antiques, yoga & more. Walk the tranquil, peaceful neighborhood, launch our kayaks @ end of block. Relax/enjoy! Learn More
Our charming beach cottage has hard wood floors throughout and is bright and airy. It sleeps up to 5 in our 2-3 bedrooms. The 1st bedroom is the spacious master with queen bed, ceiling fan, alcove & walk in closet. The 2nd bedroom is cozy with a full size bed, ceiling fan & closet. We also have a lovely room we call the blue room that during the day is set up with a new queen size sleeper sofa. At night just close the french doors, open the couch to a bed and relax taking in the North F...
Perfect family vacation home and those seeking a quiet relaxing setting. Guests will have access to the complete home, deck, pool, grill and beach privileges Completely private to renters The bay is I mile away and you are able to walk to Main Street. Accessible by LIRR at Mattituck Station. Please inquire about special pricing Guests will have access to the complete home, deck, pool, grill and beach privileges. Completely private to renters The bay is I mile away and you are able...
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