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1000+ Rentals · Southold
1000+ Rentals · Southold
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...
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...
Just two hours from New York City, you can enjoy a quiet get-away on the North Fork of Long Island. The house is a late 19th-century farm house situated on the main road -- a convenient walk to/from the LIRR, Jitney Stop, 3 blocks to town, and 5 blocks to the town beach. Literally everything is located steps from the door: beach, harbor, SI ferry, transit, boutiques, restaurants, bars, cafes, antique shops, yoga, and the list goes on. This house was built in the late 1800's but it's now 2...
Lovingly restored and maintained historic home with antique furnishings throughout. Situated on a quiet residential street just steps from shops, galleries, restaurants and beaches - no car necessary! A perfect getaway just two hours from NYC. Learn More
Historic home with wood floors and antique furnishings throughout. Upstairs: three cozy bedrooms (two double bedrooms and two twin beds) plus an additional playroom/sitting room; three en-suite bathrooms. Downstairs: ample eat-in kitchen with glass doors opening onto the porch and garden; dining room with large dining table; living room with working fireplace; sun-lit office. Guests can access all rooms in the house. The backyard studio will not be available to guests. I will give you t...
Cozy secluded 1BD apartment; sleeps up to 6. Located in the exclusive Fleets Neck community in Cutchogue, the heart of the North Fork East End. Short walk to Cutchogue Harbor, Wickham Creek and/or Pequash Beach. Access to all area Fun Attractions. Learn More
Year round wooded sanctuary in the exclusive Fleet's Neck community of Cutchogue, on the East End of Long Island. With one bedroom featuring a queen size bed, the spacious main living space features comfortable queen and full size bed pull out sofa beds with a privacy curtain available. Refrigerator, microwave and coffee maker available. The apartment offers quiet wooded tranquility, only a walk away from Cutchogue Harbor, Wickham Creek and the exclusive Fleet's Neck beach as well as downt...
Our newly renovated beach cottage in the heart of the North Fork is minutes from wineries, golf, boating, antiques, organic farms, fishing, fabulous restaurants, yoga & more. Launch our kayaks at end of the block & great beaches just minutes away. 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...
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. ...
AVAILABLE TO RENT: Flexible Our family waits to go there and hates to leave! Our house located on the North Fork in the middle of beautiful beaches and wonderful vineyards and just two hours from New York City. Set on 1.9 acres it is Great for groups with a 5 bedroom, 5 bathroom newly renovated main house with a separate loft studio apartment (not renovated but nice) above the garage. Perfect for children and their endless adventures. The house is located on exclusive Nassau Point where y...
Our house is located in Cutchogue, the heart of the North Fork. Our half acre, two bedroom, 1.5 bath house has a private dock, two kayaks, outdoor shower, enclosed yard w/swing set, outdoor grill, fireplace, cable/ Internet and 1/2 mile to beach. Learn More
Our property is long, flat and gorgeous with the water out back. Guests can have a ball there being acitive such as fishing, kayaking, playing ball, badmitton, soccer and the list goes on. Guests have access to the property, dock, shed, basement and yard. Feel free to contact us via email, text or phone if you have any issues or questions. Our neighborhood is very quiet, friendly and close to beaches, stores and wineries. Car, bike or walking is the preferred mode of transportation ar...
Charming, bright and open 3 bedroom 2 bath ranch in peaceful Broadwaters Cove neighborhood. Boat launch 2 blocks away, and Nassau Point beaches just a short 10 minute walk! Centrally located in North Fork Wine Country! Learn More
Historic waterfront property in scenic North Fork wine country. Private beachfront with modern amenities, beautifully appointed and family friendly. The perfect summer getaway...memories are made here! Learn More
Built to preserve a late 19th century fishing club, a large brick hearth and wooden beams grace the living room. History and luxury combine to make this a one of a kind vacation home. Waterfront with private beach, beach chairs, kayak, hammock, gas grill, wifi, cable tv, washer/dryer, dishwasher, working fireplace. Wineries, fishing, boating, golf, great restaurants, quaint towns, farm stands, horseback riding all nearby. There is a jitney bus to and from NYC airports and daily trains t...
Enjoy the beauty of old and new! Learn More
As you enter onto a long cobble stone driveway passing through 12 foot high privacy hedges to find a 1900 year old horse barn with beautiful farm views. The living area of the barn has two bedrooms with queen beds, full bath and mudroom with washer and dryer. The kitchen has soap stone counter tops, stainless steel appliances and butcher block center island with a porcelain farm sink opens up to the living room with French door leading into the court yard. There is ample parking for 10 cars...
Pool upon avail. Incl'd Wifi no stream, Cab, AC, He, Ele. Add clean avail+$50fee, req'd clean 3 days+$50fee, 3nts min for hol & hol wknds, No Pets, No Smoke, no diving/juming/pushing/run in around pool Learn More
Great location in the Hampton's, near the Ocean Beaches, Fishing and Boating in the Bay, Kayak the Ponds and River, Go to Wine Tastings at the Vineyards, Organic Farmers Markets and Pick Organic Foods at the farms, Close to many Hampton's Towns on the North and South Forks and Restaurants and Entertainment, Village shops, the Tanger Outlets, easy access from NYC, via car, Hampton a Jitney and Train, just to name a few points. The Main House Mini Studio The Gardens The Yard If you want to u...
Located on a quiet road, this 4-BR, 2 bath house is the perfect place for a week-long Hamptons retreat with a private backyard, htd pool and newly renovated kitchen and pool house. Just a 5 minute walk to town or bay and 10 minute drive to the beach. Learn More
The kitchen, bathrooms, basement and poolhouse are all newly renovated. The property is a five minute walk from the Hampton Jitney and a 10 minute drive to the Westhampton train station.
Steps from shops, restaurants and the bay, enjoy a relaxing stay at a charming Victorian. Private bedroom and bath with your own entrance and access to a sunny pool area. Ocean beaches are just a short drive away! Learn More
We live in an old Victorian that was added on to and previously run as a B&B. We are slowly making our own improvements! The guest accommodations are private, quiet and have their own entrance. We are happy share our pool area, garden and porch with our guests. The wrap-around porch or pool area are great for relaxing. We also have an outdoor dining table and a large backyard with fruit trees and flowering plants. If you are traveling with children, feel free to enjoy the playhouse, swing...
Beautiful, fully renovated waterfront home w/bay beach. Enjoy sweeping water views from every room including open kitchen & sunroom w/ TV & Wifi. Cool off in bay, kayak, collect shells & take quiet walks. Close to ocean beach, shopping & restaurants. Learn More
Beautiful, fully renovated bayfront home with beach, beachside playground, and nature preserve. Great for family or small group. Enjoy sweeping bay views from every room including open kitchen, swim in shallow bay waters, fish, kayak, and collect shells. Close to ocean beaches, hiking trail, wildlife refuge, deep water fishing, water sports, fresh seafood, aquarium, water park, and other eastern Long Island activities (North Fork and South Fork). Shopping and dining in villages of Westhampt...
Zen Cozy comfortable Artist home .Drinks by the fireplace for a romantic night. Room available comfortable queen size bed , mini fridge,cable, wi-fi, w/d, quite neighborhood near all shopping accommodations, and Beaches.Transportation available. Learn More
Local ARTIST HOME : freshly painted. Room-Queen size bed , wall unit for lost of storage, closet which houses TV and dresser.Mini fridge in room optional for short stay ,wi-fi, cable. Room rented for Summer or Yr, round if needed Master Bedroom- Available for weekends only 2-3 days depending on the weekend just ask....if available higher rate $110 for off season .Summer $145 per night sleeps two WASHER DAYER , MASTER BATH. KITCHEN, LIVINGROOM. COFFEE MACHINE. MICROWAVE, You much clean af...
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