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1000+ Rentals · Shelter Island
1000+ Rentals · Shelter Island
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
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.
2 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...
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...
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...
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...
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 ...
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
We are available. Please call-email us if you need assistance Quite, peaceful Smart TV in the house. You would need your Netflix, Amazon prime or Hulu etc. account to watch your favorite shows.
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...
"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.
Water view home located near the South Ferry. This 2 story coastal home is perfect for families or small groups looking for a comfortable and peaceful place to vacation. The rental includes walking trails, beach cruiser, fire pit, large backyard and deck, trampoline, jungle gym, swing, books, toys and games for the kids, and short drive to town (restaurants, shops, Nature Conservancy). We look forward to making your stay as pleasant as possible! Learn More
Guest will have access to the main living spaces in our two story house as well as the grounds (including walking trails). The basement/garage and attic will be where we store our personal items so we would consider that space the only space to be inaccessible to guests.
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
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 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
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...
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...
I have a 1930's renovated farmhouse, I have one common room with continental breakfast included. 4 private bedrooms each contain private bath. For reservation call 631-466-2977 or 631-749-3208, all weekends have minimums Learn More
Front of home, by parking area I am available at any time of day!
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...
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