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1000+ Rentals · Shelter Island
1000+ Rentals · Shelter Island
3 -night minimum. Learn More
a newly constructed, 600 square foot, 2nd floor cottage with oak floors, skylights, southern-facing wall of glass and large deck overlooking the treetops. there is a queen bedroom, and daybed in the living room, to sleep a total of 3 people. full kitchen, washer/dryer, large bathroom with shower, cable, wifi, iPod dock, grill, beach chairs etc. the bedroom walls are 8 feet, but do not reach the ceiling, for comfortable air circulation. the place is clean, comfortable and easy to spend...
Two recently renovated and very charming rooms in a separate and private wing of our home are available to rent on a daily or weekly basis. Each room has a separate entrance and private bathroom. All rates are for single or double occupancy. Learn More
Come and experience the elegance and beauty of Shelter Island. Shelter Island is nestled between the North and South Forks of Long Island. Shelter Island can be reached via ferry from Greenport to the north or from North Haven to the south. Room M1 can accommodate four people. +$25 for each additional person; Room M2 can accommodate two people. All rates are for single or double occupancy. There is a two night minimum on weekends and a three night minimum for Memorial Day, 4th of July, ...
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. Learn More
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.
Charming secluded Shelter Island Cottage. Three bedroom one and a half bath. Cozy and quirky, sleeping lofts in converted attic accessed by a spiral staircase built from a telephone pole. Half an acre surrounded by nature preserve and bamboo. Learn More
One bedroom dowstairs with queen sized bed, two quirky sleeping lofts/bedrooms in converted attic complete with skylights, accessed by hand hewn spiral staircase. Low ceilings upstairs! There is also a single bed on the porch. Filled with artwork and love. Complete with cotton sheets and duvets, towels and toiletries, beach chairs and beach towels, toys and umbrella, cereal and coffee. Fully outfitted kitchen with blender, microwave, toaster oven, dishes and pots and pans. D/W, W/D, and ru...
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 Sears and Roebuck classic beach house with water views from the living room, den, upstairs bedroom, kitchen and front porch. Very comfortable-- welcomes sandy bathing suits. 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 with a double bed, and a mas...
Newly renovated 4 bedroom/3.5 baths w/ plenty of room for entertaining extended families and friends! Open concept kitchen & dining - all new appliances 3 spacious living areas + finished Basement w/ TV & airhockey Wrap around front/back deck & pool Learn More
Large newly renovated home on a secluded 2 acres, offering maximum privacy for your stay. Brand new open concept kitchen with all new appliances, kitchen island with seating and farm table dining. Comfortable living room with TV and fireplace and two sun rooms to enjoy your morning coffee and a book. Each TV has digital cable, and house has hi speed WIFI extenders throughout to offer maximum range for work or entertainment. Beautiful master suite with king size bed and a brand new spa b...
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...
Contemporary, light filled,open plan, 3-bedroom, 3-bath home with a spacious deck overlooking an acre of green lawns, lush foliage and a small koi pond. Filled with modern art, designer furnishings, state of the art appliances, AC and no clutter. Learn More
The house has a modern and luxurious feel with designer furnishings and accessories. The open plan makes it perfect to entertain in along with the deck with sunlight all afternoon. Every bedroom has an en suite overlooking the garden. Guests will have access to everything including a two car garage and a bike. Getting on the South Ferry (only 4 mins) from North Haven to get to the island is quite unique. The South Ferry runs every 10 minutes from 6am to midnight and until 1:45am on the we...
Newly renovated 2 bedroom 2.5 bath with kitchen/LR hard wood floors, centrally located. Central AC, Parking, WIFI, Cable TV. Rental is one bedroom and private bath, access to living room SLEEPS 2 PEOPLE 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.
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.
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, take a run or walk our neighborhood,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 her...
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.
This newly furnished and elegantly decorated 4brd/3bath is an exciting new edition to the summer rental market. Boasts a wrap-around porch, two large decks, turrets, freshly painted open floor plan with abundant natural light, vaulted ceilings. Learn More
4 bedroom with A/C on Shelter Island. Open floor plan - great beach house feel. Kitchen, Basement, Living Room, Great Room Will be present from time to time. Amazingly clear view of the sky and stars at night No public transportation, but you can get around most of the island on a rented bike. Great place to go hiking
Enjoy your summer at this fresh and inviting completely renovated 3 bedroom, 4 bath home on 1.12 acres. Some of the many highlights are a sunny open layout including living room with elevated ceilings, dining area with ...... (continued below)... Learn More
......screened porch and entertainment deck overlooking beautiful dickerson pond, organic garden, kitchen with breakfast area, outdoor shower and finished lower level. The grounds are decidedly park-like, bordering a wonderful 8 acre preserve and tranquil pond, a favorite spot for migratory birds. Lounge by the pool and enjoy the natural scenery! There is deeded access to Menantic Creek for kayaking and boating and just a 5 minute stroll o the island boatyard marina and Salt restaurant
Rent 1 bdrm for 2 (daily) or entire 5 bdrm house (wkly/monthly) sleeps 8. Walk to Sunset Beach. 3 day min. 2 King, 2 Twins, 2 Full beds, 1.5 baths & outdoor shower. Glorious sun room, country kitchen. Grocery, Tuck Shop ice cream, beaches close by. Learn More
This home, built in 1888 by a sea captain, is listed in the historic register on exclusive Shelter Island. This is the first time in 40 years this house is open to the public. Each designer bedroom has comfort mattress, brand new 1,000 count cotton sheets, ceiling fans, plush towels for home and beach towels and chairs provided. Designed to help you exhale and unwind. Traditional wrap around porch. NYC guests can come via Jitney and take a 5 minute cab ride to house once the North Ferry ...
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 ...
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