Important: This destination may have COVID-19 travel restrictions in place, including specific restrictions for lodging. Check any national, local, and health advisories for this destination before you book.

tom owens on trover

Find Hotels in Shelter Island, NY

Search over 1 million properties and 550 airlines worldwide

Members save 10% more on select hotels, cars, activities and vacation rentals. Sign up.

Free cancellation on most hotels. Because flexibility matters.

Shelter Island hotels and places to stay

Brand New House in Beach Community on Shelter Island, NY
Private Hamptons Cottage
Shelter Island, NY
Get Rates
0.67 mi from city center
No reviews
Paradise

"Fantastic!"…"

Reviewed on Sep 9, 2019

Private Hamptons Cottage
Shelter Island Waterfront House With Dock And Private Beach
Get Rates
0.43 mi from city center
5/5Exceptional! (13 reviews)
Great stay

"Perfect location and great house. Has everything you need for your stay. 1 minute walk to the beach for swimming. Nice deck to enjoy coffee in morning and drinks in evening"…"

Reviewed on Aug 20, 2019

Shelter Island Waterfront House With Dock And Private Beach
New Listing: Renovated & Modern, Waterviews, Walk to Beach, Heated Pool/hot Tub
New Listing: Technicolor Paradise, Architectural Masterpiece Amidst Woodlands & Beaches, Pool
4.4/5Excellent! (5 reviews)

"Overpriced. Beds good. Uncomfortable and not well equipped."…"

Reviewed on Sep 24, 2019

New Listing: Technicolor Paradise, Architectural Masterpiece Amidst Woodlands & Beaches, Pool
NEW Listing: Farmhouse Renovated w/ Convenience + Comfort, Stylish and Charming Living
No reviews
Beautifully designed and plenty of amenities

"This home exceeded our expectations in every way. The house is meticulously designed and at the same time feels warm and homey - almost like staying at an Friends’ house that is an interior designer by trade. The kitchen/dining room was perfect for group dinners - had everything you could want and ..."…"

Reviewed on Aug 30, 2019

NEW Listing: Farmhouse Renovated w/ Convenience + Comfort, Stylish and Charming Living
Aqua by American Beech
2.5 out of 5
15 Bay Ave, Aquebogue, Riverhead, NY
The price is $239 per night
17.16 mi from city center
4.6/5Exceptional! (133 reviews)

"Extremely accommodating, very clean and comfortable."…"

Reviewed on May 18, 2020

Aqua by American Beech
Marram
4 out of 5
21 Oceanview Terrace, Montauk, NY
Free CancellationReserve now, pay when you stay
The price is $345 per night
19.69 mi from city center
4.4/5Wonderful! (30 reviews)

"The own beach access was awesome and also the friendliness of staff. You did not even have to ask for certain things, they were just provided."…"

Reviewed on May 30, 2020

Marram
Haven Montauk
2.5 out of 5
533 Westlake Drive, Montauk, Montauk, NY
Get Rates
19.4 mi from city center
4.4/5Wonderful! (130 reviews)

"Liked location. Toilet kept running and we had to adjust it many times. Would return to this property next time we were in Montauk."…"

Reviewed on Oct 26, 2019

Haven Montauk
Beachcomber at Montauk
3 out of 5
727 Old Montauk Highway, Montauk, NY
The price is $329 per night
18.59 mi from city center
4.5/5Wonderful! (167 reviews)

"The Beachcomber at Montauk is a condominium complex that rents out units to vacationers. It is not a hotel. There are, therefore, no hotel amenties like a restaurant, a lobby or any shops -- much less a desk. This was disappointing. The grounds of the property are beaitiful --with a large swimming ..."…"

Reviewed on Dec 6, 2019

Beachcomber at Montauk
Can't find the property you want?
See all available properties in Shelter Island
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Visiting Shelter Island

Visitors can enjoy all that Shelter Island has to offer including the parks, beaches, and museums. This city also attracts tourists with its scenic landscape.

  • There are 3 hotels and other accommodations in Shelter Island
  • The closest major airport is in East Hampton, NY (HTO), 7.6 mi (12.2 km) from the city center
  • The next closest is in Fishers Island, NY (FID-Elizabeth Field), 20 mi (32.2 km) away

Sightseeing and Staying in Shelter Island

Notable city landmarks like Havens House and Sylvester Manor might be worth a visit. The picturesque setting of Mashomack Preserve and Wades Beach exemplify the city's natural beauty. Additionally, you might want to add Shelter Island Historical Society to your agenda.

As you make plans for a getaway to Shelter Island, your ideal accommodation may not be in the heart of the city but you'll find 241 hotels and lodging options locally. Below are places to stay in the area:

  • Immaculate New Construction Summer Getaway Home on Shelter Is. With Heated Pool is 1.5 mi (2.4 km) from the center of Shelter Island. This 3.5-star resort in Westbrook features a full-service spa, a private beach, and 3 restaurants. Our customers like its bar and clean, comfortable rooms.
  • Summer On Shelter Isle is 1.3 mi (2.1 km) from central Shelter Island. Guests who stay at this 4-star resort in Montauk can enjoy access to a full-service spa and a private beach, along with free WiFi. It's a favorite with Expedia travelers for its helpful staff and clean, comfortable rooms.
  • Joyful and Chic on Shelter Island is located 1.4 mi (2.2 km) from the heart of Shelter Island. This 3.5-star hotel in Montauk features a marina, 2 outdoor pools, and a private beach. It's a favorite with Expedia travelers for its family-friendly amenities and dining options.

Dressing for Shelter Island

  • Between January and March, daytime temperatures average 52°F, while nighttime temperatures stay around 19°F
  • From April to June, the average is 79°F during the day and 31°F at night
  • July through September sees average temperatures of 81°F during the day and 46°F at night
  • In October-December, you can expect 68°F as the daytime average and 21°F as the nighttime average
  • About 46.85 inches of rain falls on Shelter Island each year
  • July and August are usually the hottest months averaging 80°F, while February and January are usually the coldest with an average temperature of 20°F

Frequently asked questions

Where is the best place to stay in Shelter Island?
If I need to cancel my hotel reservation in Shelter Island, will I receive a refund?
Yes, the majority of hotel room reservations are fully refundable as long as you cancel before the accommodation’s cancellation deadline, which is often 24 or 48 hours before your scheduled arrival. If you booked a non-refundable reservation, you might be able to still cancel and get a refund within a 24-hour period of your booking. Enter dates in and click on “Search”, then you can filter by “free cancellation” to get the best deals in Shelter Island.
Where can I learn more about changing or cancelling my trip to Shelter Island?
For additional details about picking new dates or cancelling your trip to Shelter Island, click here.
Where is the best hotel to stay with easy access to Mashomack Preserve?
The Chequit Inn is one of the top choices for your stay based on our traveler data, and this 4-star hotel offers free breakfast and a restaurant. It’s located 2.6 mi (4.2 km) from Mashomack Preserve. Other good choices within 5 miles include West Neck Guesthouse and Shelter Island House.
What about the best place to stay near Havens House?
One of the top choices for your stay is The Chequit Inn, located 1.8 mi (3 km) from Havens House, and this 4-star hotel offers free breakfast and a restaurant. West Neck Guesthouse and Sound View Greenport are a couple of other good options within a few miles.
What are some accommodations with pools in Shelter Island?
Montauk Manor: Offers an indoor pool, a seasonal outdoor pool, and a restaurant.
What is the best accommodation for staying close to John F. Kennedy International Airport (JFK)?
Holiday Inn Express Kennedy Airport is a popular hotel, featuring free breakfast and free WiFi. It’s located a short 1.5 mi (2.5 km) from John F. Kennedy Intl. Airport. Other options near the airport are Fairfield Inn by Marriott JFK Airport and Radisson Hotel JFK Airport.
What's it like to stay in Shelter Island?
Visitors can enjoy all that Shelter Island has to offer including the parks, beaches, and museums. This city also attracts tourists with its scenic landscape. A top sight in the area is Cooper’s Beach. In Shelter Island, there are 9 hotels and other accommodations to choose from.
What should I see while I'm in Shelter Island?
Landmarks like Havens House and Sylvester Manor might be worth a visit. The picturesque setting of Mashomack Preserve and Wades Beach exemplify the area’s natural beauty. Additionally, you’ll find Cooper’s Beach in the area.
What's the weather like in Shelter Island?
The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 33°F. Average annual rainfall for Shelter Island is 47 inches.

Recent reviews of Shelter Island hotels

More trip options