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1000+ Rentals · Shelter Island
1000+ Rentals · Shelter Island
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...
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.
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...
Shelter Island Cottage Quite getaway - 2 Br / 2 Bath cottage on Shelter Island. Close to everything. Contact me for weekly and monthly rental pricing. Learn More
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 (no d/w), 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...
Come Join Mary Ann and Paul at their summer wonderland, share the whole house with them, kitchen, LR, the pool, deck area; 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! 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. 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 permits, we could do that! Depends on the guests, and how they want to spend their time, we are amenable to sharing meals, and have a gas grill; t...
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 and 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, and Labor da...
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.
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...
Charming, comfortable beach home decorated with great style. Fantastic in and outdoor entertainment spaces, wide water views and striking sunsets from the deck. Large gunite pool, steps from best south facing (Wades) beach on Shelter Island. Learn More
Steps from beautiful south facing bay beach, (beach has pick nick tables & facilities) Large eat in kitchen with all modern appliances Charming sitting room with fireplace for cozy evenings Separate playroom with TV Spacious master bedroom with stunning waterviews from large deck which is also great for entertaining! Large outdoor covered porch for eating and terrace with outdoor sofas for relaxing and entertaining Large garden, lots of room for playing sports Vegetable and herb garden - pl...
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.
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 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
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...
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, 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 linens. Walking distance ...
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...
Beautiful post and beam house on an acre presents as the quintessential Shelter Island living. Wrap around porch enhances all outdoor entertaining and provides a vantage of the gunite pool. The kitchen and bathrooms are newly renovated. Learn More
Smart TV in the house. You would need your Netflix, Amazon prime or Hulu etc. account to watch your favorite shows.
A room in our centrally located Bed and Breakfast with two twin size beds 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 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 F...
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