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Tonight
May 12 - May 13
Tomorrow
May 13 - May 14
Next weekend
May 17 - May 19

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Top hotels and accommodation in Shelter Island

Seasonal outdoor pool, pool umbrellas, pool loungers
The Pridwin Hotel
3.0 star property
10.0 out of 10, Exceptional, (20)
"Very elegant "
The price is NZ$567
per night
14 May - 15 May
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 NZ$1,022
per night
19 May - 20 May
Canoe Place Inn and Cottages
Exterior
Chic & Serene in The Hamptons. 1 block to waterside dining and the best sunsets
10.0 out of 10, Exceptional, (1)
"Friends and I stayed the weekend at this rental and loved it! We cooked, watched a movie, played board games, and enjoyed the fall weather. It is in a quiet neighborhood that is an easy drive to town, beaches, and nature preserves. Lisa is a very responsive and gracious host! Would definitely recommend!"
Chic & Serene in The Hamptons. 1 block to waterside dining and the best sunsets
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Garden
The Farmhouse Bed and Breakfast
3.5 star property
10.0 out of 10, Exceptional, (5)
"The Farmhouse was a perfect stay for a relaxing weekend in beautiful surroundings. The Farmhouse is charming and impeccably kept. The hosts are friendly and amazing cooks. Added plus : a destination charger for our Tesla! Definitely recommend!"
The Farmhouse Bed and Breakfast
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 NZ$789
per night
14 May - 15 May
East Hampton Art House Bed & Breakfast
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 NZ$1,128
per night
14 May - 15 May
The Roundtree, Amagansett
Property grounds
The Hedges Inn
3.5 star property
9.6 out of 10, Exceptional, (66)
"Beautiful location and lovely accommodation."
The Hedges Inn
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 NZ$474
per night
14 May - 15 May
Colonial Shores Resort
View from property
House on Chase Creek
2.5 star property
9.4 out of 10, Exceptional, (63)
"543y"
The price is NZ$523
per night
14 May - 15 May
House on Chase Creek
Property grounds
Bridgehampton Inn
3.5 star property
9.4 out of 10, Exceptional, (205)
"I will never NOT stay there when I’m in the area. The restaurant should have a Michelin star and the cocktails were inventive and delicious. The rooms had fireplaces- it was perfect on a storm night. The coffee is was excellent and the beds soft. If I could give it 10 stars, I would."
The price is NZ$862
per night
14 May - 15 May
Bridgehampton Inn
Property entrance
Southampton Village Motel
2.5 star property
9.2 out of 10, Wonderful, (42)
"My room was unacceptable, there was mold and the shower was flooding the bathroom all the time, the wifi did not work very well and the owner/manager was not helpful. I had to call every time we needed more towels and she was not welcoming or friendly at all. When we told her about the shower she did not show any remorse"
The price is NZ$756
per night
14 May - 15 May
Southampton Village Motel
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 NZ$240
per night
28 May - 29 May
Hampton's Vacation Inn
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 NZ$384
per night
14 May - 15 May
Hampton Maid Motel
1 bedroom, WiFi, bed sheets
Sag Harbor Suite by the Beach
9.0 out of 10, Wonderful, (8)
"We were in town to celebrate thanksgiving. Nice cozy 1 bedroom apartment. 5 minute drive to town."
Sag Harbor Suite by the Beach
Outdoor spa tub
The Drake Inn
2.0 star property
9.0 out of 10, Wonderful, (77)
"The hotel was very clean and the location was very good. It was close to restaurants and beach."
The Drake Inn
Deluxe Studio | Living area
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 NZ$596
per night
14 May - 15 May
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 NZ$555
per night
27 May - 28 May
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 NZ$938
per night
14 May - 15 May
Mill House Inn
Seasonal outdoor pool, open 8:00 AM to 8:30 PM, free pool 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 NZ$278
per night
14 May - 15 May
Bayview Resort
Desk, free WiFi, bed sheets
Southampton Long Island Hotel
2.5 star property
8.4 out of 10, Very good, (165)
"Awesome stay -- room was very clean and bed was really comfortable. They also upgraded us to a deluxe room at no charge! Would stay again. "
The price is NZ$346
per night
14 May - 15 May
Southampton Long Island Hotel
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Frequently asked questions

If I need to cancel my hotel reservation in Shelter Island, will I receive a refund?

Yes! You'll find that most hotel bookings are fully refundable if you cancel before the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If your reservation is non-refundable, you might be able to cancel it and receive a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Shelter Island.

What is the best spa hotel in Shelter Island?

Waterfront House With Dock And Private Beach

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 accommodation options 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 itinerary are Gardiner's Bay Country Club and Shelter Island Historical Society. Take a look at what more there is to see and do in Expedia's Shelter Island guide.

What's the seasonal weather in Shelter Island?

The hottest months are usually August and July, with an average temperature of 21°C, while the coldest months are January and February, with an average of 3°C. Average annual precipitation for Shelter Island is 1452 mm.