Find hotels in Shelter Island, NY from ₩121,890

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May 13 - May 14
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May 14 - May 15
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May 17 - May 19
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Compare 4,792 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Seasonal outdoor pool, pool umbrellas, sun loungers
The Pridwin Hotel
3.0 star property
10.0 out of 10, Exceptional, (20)
"Everything was exquisite! "
The price is ₩409,035
₩513,497 total
includes taxes & fees
May 14 - May 15
The Pridwin Hotel
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
Canoe Place Inn and Cottages
4.0 star property
10.0 out of 10, Exceptional, (26)
"Absolutely the nicest hotel in the area. "
The price is ₩737,358
₩883,590 total
includes taxes & fees
May 19 - May 20
Canoe Place Inn and Cottages
Aerial view
East Hampton Art House Bed & Breakfast
4.0 star property
9.8 out of 10, Exceptional, (53)
"Beautiful property and Michael and Rosealind are some the nicest hosts we have ever encountered. "
The price is ₩569,092
₩649,476 total
includes taxes & fees
May 14 - May 15
East Hampton Art House Bed & Breakfast
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Beach nearby, white sand, sun loungers, beach umbrellas
The Roundtree, Amagansett
4.5 star property
9.8 out of 10, Exceptional, (75)
"The best hotel in the Hamptons! Luxury hospitality without pretension. Quiet, simple and the only one worth the price tag. You will pay the same if not more at any other local hotel and receive the worst service. It would be so easy for Roundtree to just rely on the high summer months to make money and rob you because they can, but they don't. The whole team works with an integrity uncommon to the area. Easy walk to everything in town and while they don't have a restaurant or bar they make up...
The price is ₩813,966
₩975,382 total
includes taxes & fees
May 14 - May 15
The Roundtree, Amagansett
Reception
The 1770 House Restaurant & Inn
4.0 star property
9.8 out of 10, Exceptional, (135)
"beautiful inn with a scenic setting"
The price is ₩403,563
₩560,679 total
includes taxes & fees
May 21 - May 22
The 1770 House Restaurant & Inn
Property grounds
The Hedges Inn
3.5 star property
9.6 out of 10, Exceptional, (66)
"Beautiful location and lovely accommodation."
The Hedges Inn
Outdoor pool
Sag Harbor Inn
3.5 star property
9.4 out of 10, Exceptional, (421)
"We found the staff very welcoming. The room was clean & neat. The view from our little balcony was awesome. It’s a quiet spot this time of the year and we enjoyed our welcome very much. We look forward to staying here on our return.."
The price is ₩320,114
₩365,330 total
includes taxes & fees
May 16 - May 17
Sag Harbor Inn
Outdoor pool
Topping Rose House
4.5 star property
9.4 out of 10, Exceptional, (105)
"Noise from other guests."
The price is ₩950,767
₩1,089,852 total
includes taxes & fees
May 22 - May 23
Topping Rose House
Aerial view
Colonial Shores Resort
2.5 star property
9.4 out of 10, Exceptional, (81)
"This is our second 8 day stay. Here for work (Hanging Wallpaper) we really enjoyed our time here. Around the corner from everything. "
The price is ₩342,003
₩390,321 total
includes taxes & fees
May 15 - May 16
Colonial Shores Resort
Terrace/patio
The Bentley Hotel Southampton
2.0 star property
9.2 out of 10, Wonderful, (69)
"We had a great stay"
The price is ₩238,855
₩330,309 total
includes taxes & fees
May 16 - May 17
The Bentley Hotel Southampton
Exterior
The Rams Head Inn
3.0 star property
9.2 out of 10, Wonderful, (7)
"It's traditional, quaint, serene, and the air is fresh"
The price is ₩328,145
₩374,479 total
includes taxes & fees
May 19 - May 20
The Rams Head Inn
Front of property - evening/night
Baron's Cove
3.5 star property
9.0 out of 10, Wonderful, (133)
"We loved everything about our stay - the location, the cleanliness, the service, Kristen at the front desk :-), the food (we had breakfast and brunch at the hotel during our two days there) - can't wait to go back to Baron's Cove!!!!"
The price is ₩409,035
₩513,497 total
includes taxes & fees
May 15 - May 16
Baron's Cove
Children's activities
Hampton's Vacation Inn
2.5 star property
9.0 out of 10, Wonderful, (234)
"The bathroom was very clean with nice plush towels. The room was also very clean with a comfortable bed. I would definitely recommend this Inn to my friends and relatives. Great location as well!"
The price is ₩173,053
₩197,499 total
includes taxes & fees
May 28 - May 29
Hampton's Vacation Inn
Outdoor pool
A Room At The Beach
3.0 star property
9.0 out of 10, Wonderful, (70)
"nice location "
The price is ₩649,805
₩741,598 total
includes taxes & fees
May 14 - May 15
A Room At The Beach
Property grounds
Hampton Maid Motel
2.5 star property
9.0 out of 10, Wonderful, (522)
"The property is well kept and beautiful. I will definitely come back. "
The price is ₩277,022
₩316,152 total
includes taxes & fees
May 15 - May 16
Hampton Maid Motel
Deluxe Studio | Living area | TV
East Hampton House Resort
3.0 star property
8.8 out of 10, Excellent, (227)
"Very convenient with own entrance and back deck and parking right in front!! Can walk to dining and breakfast options or make in your own kitchen nook!! "
The price is ₩430,376
₩520,884 total
includes taxes & fees
May 16 - May 17
East Hampton House Resort
Exterior
Journey East Hampton
4.0 star property
8.8 out of 10, Excellent, (88)
"Loved the room, bed was comfortable, shower was lovely. Cindy gave great suggestions on where to go."
The price is ₩400,143
₩502,333 total
includes taxes & fees
May 27 - May 28
Journey East Hampton
Front of property - evening/night
Mill House Inn
5.0 star property
8.8 out of 10, Excellent, (50)
"Excellent facility and excellent service. Highly recommend. "
The price is ₩615,605
₩772,830 total
includes taxes & fees
May 14 - May 15
Mill House Inn
Front of property
The Wainscott Inn
3.0 star property
8.6 out of 10, Excellent, (92)
"Looks like the were in the process of updating? Lots of construction people and debris but we also went during off season so it made sense. Have to drive everywhere but still convenient!! "
The Wainscott Inn
Seasonal outdoor pool, open 8:00 AM to 8:30 PM, free cabanas
Bayview Resort
2.5 star property
8.6 out of 10, Excellent, (372)
"The view of the bay is incredible ( I was on 2nd floor) but the structure itself needs some t l c, fresh paint, more tables in room, etc. "
The price is ₩200,277
₩237,705 total
includes taxes & fees
May 14 - May 15
Bayview Resort
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Frequently asked questions

Where is the best place to stay in Shelter Island?

Located 17.3 mi (27.9 km) from the heart of Shelter Island, Quality Inn Old Saybrook - Westbrook is a top choice for your stay based on our traveler data. Other good choices for your trip to the area are Gurney's Montauk Resort & Seawater Spa and Montauk Manor. See all available top hotels, or vacation rentals 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. Filter your search by fully refundable to find flexible hotel 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 Harborfront Inn is one of the top choices for your stay based on our traveler data, and this 3.5-star hotel offers free breakfast and a 24-hour fitness center. It's located 3.7 mi (6 km) from Mashomack Preserve.

What about the best place to stay near Havens House?

One of the top choices for your stay is The Harborfront Inn, located 3.1 mi (4.9 km) from Havens House, and this 3.5-star hotel offers free breakfast and a 24-hour fitness center.

What are some accommodations with pools in Shelter Island?

Quality Inn Old Saybrook - Westbrook: Features buffet, a pool, and free self parking. Gurney's Montauk Resort & Seawater Spa and Montauk Manor are a couple of other choices that feature an onsite pool. View all hotels with pools in Shelter Island.

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. In Shelter Island, there are 96 hotels and other accommodations to choose from. Find out more about Shelter Island.

What should I see while I'm in Shelter Island?

Natural beauty is on display at Sunset Beach, Crescent Beach, and Wades Beach. A couple of additional sights to add to your agenda are Gardiner's Bay Country Club and Shelter Island Historical Society. Check out what more to see and do in Expedia's Shelter Island guide.

What's the weather like in Shelter Island?

The hottest months are usually August and July with an average temp of 70°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Shelter Island is 57 inches.