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1000+ Rentals · Southold
1000+ Rentals · Southold
Private cottage with nearby beach for an authentic East Hampton experience in the rural/bay area of historic Springs hamlet halfway between East Hampton village and Amagansett. Loft-like living space is on 2nd floor with garden views. Learn More
A newly remodeled, open style, roomy loft space with a bohemian vibe. Table nook looks out on a garden filled with song birds, bunny rabbits, and the occasional wild turkey. Kitchenette has microwave, mini-frig, coffee maker, toaster, and kitchen utensils for light meal preparation. In addition to the modern bathroom with tiled shower, hair dryer, and all towels and toiletries, there is a rustic outdoor shower. Private driveway and private gate lead to cottage. Living space is on the secon...
Come Join Mary Ann and Paul at their summer wonderland, share the house with them, kitchen, living room, the salt water pool, deck area, with gas grill; it's 10 min walk to Wades Beach! All the peace and quiet a body could want. Kayaks,bikes available, and sailing is an option! If you are interested in the whole house, please see "Peaceful artistic sheltered retreat". Learn More
Surrounded by trees and nature, and very private! Best outdoor shower ever, there are lots of different areas to chill out. In ground swimming pool, surrounded by flower gardens and trees. This is a four bedroom private home and occasionally there may be other guests, but it is spacious, so there will never be a crowded feeling! The kitchen and shared living areas, the outdoor decks, pool, borrow a bicycle, use a kayak! There is a gym downstairs. If you like to sail and the weather permi...
We Are Located On a peaceful part of the island with 2 beaches close by. Our home Is very welcoming, relax on our Front Porch or back deck, take a run or walk, run ,kayak, swim, enjoy dinner at local restaurants. We have 2 rooms. We Have Dogs. Learn More
This is a quiet part of the island, with access to private beachs Limited use of the kitchen, the porch, and TV in living room. I leave that up to them, as little or as much as they need. Try to give them their privacy. I love the location it is a short walk to a private bay beach and very wooded. Our property is full of oak and chestnut trees. We are a short ride to excellent restaurants. You can rent kayaks, paddle boards, or relax at the beach. You need to take a ferry to get here...
This open and spacious cottage with pool offers the perfect combination of indoor and outdoor vacationing. The open kitchen, living room & dining room are comfortable gather areas for all. Walk to private beach to watch the sunset or spend the day . Learn More
"The Grove" is a charming cottage located on our private estate overlooking West Neck Bay. Ideal for a family with children, couples or friends looking to enjoy some peace and tranquility. Full access to beach & dock. Learn More
Our property is vast, private and beautiful. Explore the sunken garden, enjoy morning coffee overlooking the pond, and sunset cocktails by the bay. Parking. Washer & dryer on site. We love our guests! I (Margaret) will be there to welcome you and available to you if you have any needs or questions about the farm, cottage or Shelter Island. Shelter Island is a great place for bikers, hikers and runners. A car is convenient, but there is also a reliable island taxi service.
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/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...
Lovely renovated home on a quiet street. Modern amenities, outdoor shower, two decks, screened-in porch and more, all on a sunny half acre lot. Short bike ride to restaurants, stores and the beach. Pets considered - please ask! Two weeks minimum. Learn More
Centrally located summer cottage on quiet cul-de-sac. Two open decks in addition to a screened dining porch with seating for eight. Newly renovated kitchen and bathrooms. Dishwasher, washer-dryer, gas stove with convection oven, barbecue grill, outdoor shower with hot and cold water. Master bedroom with king-size bed, en-suite bathroom with deep soaking tub and television. Two guest bedrooms, one with a king-size bed and one with a full-size (double) bed. New mattresses, towels and bed line...
Well appointed home, stone's throw to the bay. Nicely landscaped acre of property in a quiet neighborhood. 2 blocks to town to get your morning paper, 2 blocks to the bay to sit and read it. Great area for running and biking. Walk to playground. Learn More
Relax and serve brunch to your family on the large front porch. Barbeque and entertain on the expansive deck surrounding the 20x40 pool. Child safe fencing available when needed. Keep your drinks and ice-cream close in the full size fridge in the pool house. Connect with nature in the outdoor shower. Pick fresh herbs just outside the kitchen door! Office space with desk, printer and fax so that you can work from your vacation home! Locked poolhouse and garage provided for storing you...
Our property is on 1.5 acres across from water. Super Luxurious, clean, modern. Full Gourmet Kitchen, Wood burning fireplace. Two dining areas, 2 entertainment centers. Covered Porches, all towels, linens, kitchen essentials inc. Learn More
Extremely guest friendly. Family or romance friendly - Fireplace...Plenty of space, downstairs gameroom, surround sound in multiple locations, hi-end finishes, privacy, quiet, and always super clean. Check it out listing # 3505246 on H om Eaw ay d ot c o m. Multi star multi review rating on hom e awa y. Guest have full access to entire main house unless separate provision is made for guest house. 4 bedrooms + fold out couch in L.R. 1.5 acres of privacy and luxury. 1 X King beds. 2X Queen...
This charming cottage is located on a private estate on West Neck Bay. You will have full views of the bay and access to beach & dock. Cottage is a 1 bedroom, 1 bathroom, w/ queen bed and full-size pull-out couch. Fully equipped kitchen. Wireless. Learn More
Private grounds, beach & dock. Lounge chairs overlooking West Neck Bay. Laundry on site. The cottage is located on Westmoreland Farm, a private estate. The area is quiet and peaceful, with little to no traffic. Shelter Island is a great place for bikers, hikers and runners. A car is convenient, but there is also a reliable island taxi service.
Beach ranch within walking distance of Silver Beach. Sunny, private deck with seating for 6. Large yard on quiet street. Contemporary furnishings and fresh touches throughout. Roomy living room & dining room. Master has ensuite bath. Twin bunk room and double room share hall bath with tub. Neat & clean! Learn More
Our house is 5 minutes from town by car, close to two bodies of water, and in a beautiful, quiet neighborhood. Two bikes, one kayak, beach towels. Fire pit in backyard. I can leave a key or welcome guests in person. I will be on the island in case assistance is needed but I will not be on site. The quiet street is perfect for biking or rolling the kayak down the block to West Neck Bay. Walk to nearby Silver Beach via Bootleggers Alley. There is a taxi service on the island. 3-night min...
This is a perfect getaway for families or couples, always quiet. Less than a block walk to the private Bailie Beach. If your looking to get away from the hustle and bustle, this is where you will find it - Surrounded by the Vineyards on Long Island. Learn More
Private, fully furnished 4 BR Summer home available in the Village of Mattituck, on Long Island's beautiful North Fork. Located on a quiet, no outlet residential street 10 meters away from beautiful Bailey Beach. Minutes away from the town, LIRR, finest wineries and activities. The home features 4 bedrooms with one king-size bed, two with full sized beds and 1 BR with two single beds. Each bedroom has a dresser & desk. Two full bathrooms in the home, extra large kitchen, and living room ...
This light, spacious and beautiful home is terrific for a weekend escape. Four big bedrooms and 4 bathrooms, walking distance to docks, kayaking and magnificent hiking. High ceilings, amazing stone fireplace, great chef's kitchen, and more. Learn More
Around Thanksgiving we are offering a discounted rate of $300 per night for bookings of 3 nights or more in our very quiet, tranquil retreat-like home. With a beautiful fireplace, a nearby nature preserve, not too mention fine dining around the corner this is a special place this time of year.
Upscale Country Charmer available for Weekly or Long Weekends offers 3 Bedrooms 2.5 Bathrooms plus 2 twin sleepers . This lovely home offers you the Quiet Country setting with minutes to everywhere Come enjoy and Relax in the Hampton's . Learn More
The whole house you may enjoy with respect and consideration. Except where closets are locked . I'm reachable while your a guest at my house .
Very Large Shelter Island Hts Beauty: 4 bdrms, 2 baths, + outdoor shower, large kitchen, full dining room + parlor, large living room w fireplace, wraparound porches. Walk to all: town, ferry, shops. Beach Club + Tennis + 2 kayaks included. Serenity. Learn More
Very large historic home, comfortable four bedroom, two bath + outdoor shower, large kitchen, parlor, living room, full dining room, 1885 Victorian Gingerbread Summer Home in the heart of Shelter Island Heights (11 Spring Garden Avenue at Waverly Place). Located 100 feet from the Chequit Hotel, three first floor wraparound porches (one screened in porch off the living room), two upper bedroom porches, Heights Tennis courts and private beach are a two minute walk away. Large yard + garden w...
This classic beach cottage across the street from a beach and kayak access, features a living room with den, country kitchen and large screened rocking chair porch. Enjoy dining overlooking the water and kayaking to shell beach. 4 kayaks 4 bikes. Learn More
It is a 1926 Sears and Roebuck kit beach house with water views from the living room, den, upstairs bedroom, kitchen and front porch. Very comfortable-- welcomes sandy bathing suits. Many original details As one guest remarked "it's like Maui in the sixties." The owner grew up in Hawaii and tries to maintain that true beachy feel. There is a bathroom and bedroom with twin beds downstairs. There is a second bathroom upstairs. Upstairs there is a bedroom with twin beds, a bedroom w...
One bedroom with a king size bed, adjoining large living room with a sleeper sofa, a fridge and a coffee maker, private bath. One of three apartments ( with "one bedroom with full kitchen" & "three bedroom apartment") in a two story Greek revival house in the center of Shelter Island (a short ferry ride from the Hamptons or the North Fork of Long Island, NY). Each apartment has it's own outside entrance and is rented out separately. Large grounds. Rates: weekdays from $123 to $180/night ...
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 rate $129/weekend night. Learn More
Shelter Island is the jewel of the East End of Long Island, situated between the South Fork (Hamptons) and the North Fork. Island offers beautiful beaches, kayaking, golf, tennis, hiking, biking... as well as fine dining and nightlife.
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