Beautiful, quiet and almost like a hidden gem, Shelter Island is an island and a town on Long Island in the American state of New York. Separated from Long Island by water, you can easily reach here via a regular ferry service. Home to pristine beaches, wetlands, marshes, woods and nature preserves, this island is very popular with outdoor enthusiasts interested in boating, yachting, hiking, swimming, kayaking, and more. A range of popular restaurants and bars are also located here. Visit Mashomack Preserve, Crescent Beach, Havens House, Wades Beach, and other attractions of this island with your family or friends. After a day of exploring the island, you’ll want to head back to a comfy room where you can rest and relax. Check out these 10 best Airbnb vacation rentals in Shelter Island, New York.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 09, 2024.
1. Renovated 19th-century cottage
Built in 1847, this cottage is one of the oldest homes on the island. Though it has been fully renovated, it has retained many original details, charm and character. Suitable for four guests, the cottage has a full kitchen with a dining area, a cosy living room with a fireplace, two comfortable bedrooms, a bathroom, laundry facilities, and more. Outside, there is a beautiful yard with seating. Several shops, restaurants and a beach are within a very short driving distance of the cottage.
Shelter Island, New York, United States
9.58 km (6.0 mi) from Orient Beach State ParkSuperhost
Accommodates: 4
Top guest reviews
Amenities & Room:
kitchen has all the amenities and the bed was so comfortablea comfortable and private cottagethis cottage is adorable spacious warm immaculate and so comfortableif a two-bed cottage is desired be wise and do not look elsewherecottage is adorable and charming and very comfortableCleanliness:
very clean nice outdoor spacevery clean private and homeyperfect little cottage sparkling clean and brightit is spotlessly clean with sumptuous towels sheets and pillowswhat an adorable spotless gemHost:
florence is a thoughtful hostflorence is an excellent hostflorence was a wonderful hostflorence was an amazing hostflorence is a amazing hostRead more reviewsLocation:
great place conveniently located to beacheswe also loved the locationamazing space located central to everything you need on shelter islandvery close to the ferry and easy to findgreat location for walking biking or driving
2. Beautiful house just steps from the beach (from USD 561)
Perfect for families or a group of six friends, this beautiful house is spacious and modern. It has five well-appointed bedrooms, a gourmet kitchen, elegant three and a half bathrooms, a bright and beautiful dining room, a lovely living room and an office space. Superb water views can be enjoyed from the office and the master bedroom. The house also offers plenty of outdoor amenities like a pool, a patio, barbecue facilities, and an alfresco dining on the deck. Located just across the street, the beach is easily accessible from this pet-friendly house.
Top guest reviews
Amenities & Room:
the pool is beautiful and privateCleanliness:
the house was clean and well furnished and spaciousnice place very spacious on a quaint and quiet islandHost:
karen was a gracious host and responded quickly to all my questionskaren was a great host her home was beautiful and had everything we neededRead more reviewsLocation:
a great house in a wonderful locationwhat a beautiful home and incredible locationthis house is absolutely gorgeous and in a terrific locationa great place to spend time outdoors
3. Modern home with a heated pool and a hot tub (from USD 315)
Make the most of your trip to Shelter Island by staying at this beautiful mid-century modern home that is close to a range of attractions. Ice Pond Park, a popular local ice cream spot and a public golf course are a short walk away, while a quick drive will take you to Sunset Beach, and the restaurants and bars around it. The house has a heated outdoor pool, a hot tub, a pool house, an outdoor shower, a large yard, a porch, a barbecue grill, hammock, and several other outdoor amenities. Inside, the house has an open-plan living and dining room, a full kitchen, three bedrooms and two bathrooms.
Top guest reviews
Amenities & Room:
the pool and yard at this property lives up the photos and is a nice respite on shelter islandthe beds were comfortable the kitchen well-stocked and everything we needed was at our fingertipsthe backyard well it was beyond amazing the pool and hot tub kept everyone entertained for hoursCleanliness:
such a lovely clean and beautiful homeHost:
and we were really excited in short she was everything a host can and should bejennifer was a wonderful host her house is absolutely beautiful and is a perfect weekend getawayRead more reviewsLocation:
there's a great deli that's also walkable from the house
4. Contemporary and elegant lake house (from USD 500)
Rent this serene lakehouse on Fresh Pond for a secluded stay for six guests. A private deck directly overlooks the lake and is perfect for alfresco dining. The house has a modern interior consisting of an open-concept living, dining and kitchen area, which opens out to the deck of the house. The bedrooms are spacious and offer views of the lake. Guests have easy access to the lake, which is perfect for paddle-boarding, kayaking or swimming.
Top guest reviews
Cleanliness:
the house is as described clean organized and with everything you could possibly needthe house was very comfortable clean and conveniently locatedHost:
laurie was an excellent host very responsive and provided great tips and local recommendationsRead more reviewsLocation:
the location is perfect very quaint lots of privacy and a beautiful setting
5. Charming home with plenty of outdoor amenities (from USD 300)
Bring your family along when you visit Shelter Island and stay at this charmingly pretty home that can accommodate eight guests. Experience peace and beauty as you relax in the beautiful garden or spend time in the front and back yards that have a deck, a barbecue grill, a gorgeous alfresco dining area, an outdoor shower, and a heated hot tub. Inside, there’s a modern and inviting living room, an elegant dining room, a bar, a piano, a media room, a garage full of bikes and a ping pong table, a home gym, a library, four bedrooms, a full kitchen and two bathrooms. A short walk from this house will take you to the beautiful Coecles Harbor.
Top guest reviews
Amenities & Room:
the yard hammock deck outdoor shower are beautifulit's a relaxing place plenty of space has everything you need (including an amazing outdoor shower )the beds are super firmthe only improvement i can think of is to have a little better lighting in the kitchenCleanliness:
but otherwise everything was clean and functionalhot tub was clean and easy to useisaac´s place was very clean charming and with a lot of characterplenty of space and the house was nice and clean for our arrivalHost:
his recommendations were very helpful tooisaac was a great hostisaac was a great host super responsive communicative and warmisaac is a great host and this is a hidden gem of an airbnbhe was very kind in the way he catered to our needsRead more reviewsLocation:
isaac's house was very comfortable and the perfect location for the wedding we attended this weekendthe location is great secluded quiet and serenewonderful place for a weekend away from nyc and a very good records selection on top of itthe location is very good we did enjoy a lot of biking on shelter islandgreat and cozy weekend getaway great location on the island glorious fall foliage
6. Centrally located studio (from USD 171)
Those travelling to Shelter Island as a couple will enjoy staying at this centrally located studio. Bring your furry friends along, too, for this rental is a pet-friendly one. The studio is spacious and well-furnished, with a living area, a kitchenette, a dining area, a full bathroom and a comfortable bed. You will also have access to an outdoor deck with seating. A five-minute drive will take you to the beach.
Top guest reviews
Cleanliness:
very clean and well equippedwe had a lovely stay despite a couple a cleanliness issuesHost:
karen was a wonderful host easy to communicate with and helpful overallkaren was very responsive and friendlykaren was incredibly responsive and answered any questions right awayRead more reviewsLocation:
cute place and great locationgreat central location that’s convenient to anywhere on shelter islandkaren’s studio was located in a central but beautiful part of shelter islandgreat central location private and everything you need relax and get away from it allcozy clean and in a great location of the island
7. Gorgeous farmhouse close to creek and beach (from USD 450)
With its convenient central location, this renovated farmhouse is ideal for those who want to escape the hubbub of the city. Find peace and tranquility as you relax in the inviting outdoor spaces of this farmhouse from the 1800s. There is a covered porch, a landscaped yard and plenty of seating to unwind in the natural surroundings of this lovely house. The interior is stunningly elegant, complete with an open-plan living and dining area, a modern kitchen, two chic bathrooms and three contemporary bedrooms. A creek and several conveniences like a supermarket, a bank, some restaurants and a bakery are at a walking distance, while the beach is a five-minute drive away.
Top guest reviews
Amenities & Room:
the beds are super comfortable with nice beddingCleanliness:
the beds were fabulous and everything was very cleanlynn’s farmhouse was perfect for our needs—adorable very clean and in a great locationHost:
lynn is such a lovely communicative hostRead more reviewsLocation:
the place was immaculately clean and located right in the middle of the island which was nicethis house is perfect for a quiet visit to the island
8. Family-friendly luxury beach house
Stay in style and luxury on Shelter Island by booking this amazing beach house. It can accommodate up to eight guests and is perfect for families. The highlight of this luxury house is its gorgeous heated pool. Plus, there’s a hot tub, an outdoor deck with plenty of seating, an upper-floor deck with alfresco dining facilities, and a treehouse for kids. Inside, the house is very modern and has a contemporary kitchen, an open-plan living and dining area, four elegant bedrooms and a luxurious den. Wades Beach is a three-minute walk away from this beautiful house and Mashomack Preserve is at a walking distance, too.
Shelter Island, New York, United States
10.4 km (6.5 mi) from Orient Beach State ParkTop guest reviews
Cleanliness:
very clean plenty of spaceyou can expect a beautiful comfortable home and a clean nice poolit was clean perfect location and great outdoor spacethe house was super clean the beds very comfy and the location was fantasticRead more reviewsHost:
and his property manager were responsive and helpfulthe property manager kim is super responsive and knows the island wellkim and scott were responsive approachable and warm property managersappreciated direct and fast communications with them and jc the owner
9. Furnished apartment in a Greek Revival house
Located in a lovely Greek Revival house, this apartment is fully furnished and provides comfortable accommodation for four guests. A welcoming living area, a cosy dining space, a beautiful bedroom with a king-size bed and a full bathroom are available in the apartment. Guests staying here will also have access to the beautiful grounds and an outdoor deck with seating. Many restaurants and ferries are easily accessible from this apartment.
Shelter Island, New York, United States
8.91 km (5.6 mi) from Orient Beach State ParkTop guest reviews
Amenities & Room:
the kitchen was fully equipped and we had a terrific night's sleep in the bedwe felt instantly comfortable and had everything we neededanu allowed en early check in which i really appreciated:) highly recommend this apartmentwe enjoyed the large living room and large bedroom with a very comfortable king bedCleanliness:
clean and cozyvery clean and cozy and anu made communication very easysuper beautiful and clean suitclean smooth check-in great communication and a great staysimple clean and easyHost:
the host was available and gave us good directionsanu was an amazing host - quick to help us upon check in and made us feel extra welcomegreat space great area helpful ownersanu is really helpfulanu was a great host and the place was nice and cozyRead more reviewsLocation:
great location & beautiful groundsvery comfortable and well locatedit's centrally located to many great places though they are more in driving than walking distancegreat location in center of shelter islandgreat location right in walking distance of two excellent local restaurants and the local brewery
10. Spacious apartment in the centre of the island
Explore all the attractions of Shelter Island by booking yourself and your group of six into this centrally located apartment. Located on the upper level of a Greek Revival home, the apartment offers three spacious bedrooms, one full bathroom, a fully furnished living room, a kitchen-cum-dining area and a private entrance. The house is situated on large grounds that are landscaped and ideal for relaxing or taking a leisurely walk. A charcoal grill is also available for guest use. Many shops and restaurants are at a walking distance from this Airbnb.
Shelter Island, New York, United States
8.88 km (5.6 mi) from Orient Beach State ParkTop guest reviews
Amenities & Room:
3 team members fit very comfortably in the upstairs apartmentwe had a comfortable stay the apartment is spacious with lovely light and good based for exploring the islandwe had a fantastic stay at anu's apartmenta group of friends rented out the 3br apartment and the downstairs 1brit was large and the rooms were quite charming and bright with sunlightCleanliness:
very clean and cozyclean & tidy simple decoroverall house was clean bathroom was cleanthe bathroom is cleanthe apartment is very clean and spaciousHost:
the hosts were very relaxedgreat place very nice hostanu was an excellent hosther island info was very helpfulanu was kind enough to pick us up straight from the ferryRead more reviewsLocation:
the apartment was comfortable and centrally located on the island close to the grocery store and to restaurantsthe location is great - right in the center of shelter island with easy access to either ferrygreat apartment smooth process awesome location thanksanu's place was perfect for our professional yet creative offsite workshopher house is easy to reach and walkable to shops and restaurants
Awesome Airbnbs in Shelter Island
Shelter Island is a great place to hang out with your friends and family. Due to its easy accessibility from New York City, the island is perfect for weekend getaways or day trips, too. And while planning your visit, do remember to stay at one of our recommended Airbnbs in Shelter Island, New York.
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