Shelter Island Hotels

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Top 10 trending Shelter Island hotels

Seasonal outdoor pool, pool umbrellas, pool loungers
The Pridwin Hotel
3.0 star property
10.0 out of 10, Exceptional, (20)
"Everything was exquisite! "
The price is €347
includes taxes & fees
19 May - 20 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 €554
includes taxes & fees
22 May - 23 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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Outdoor pool
Fairy Tale Guest Cottage in Magic Garden by Pool
10.0 out of 10, Exceptional, (47)
"Eunyoung and Mark have a beautiful home and have created the best “home away from home” for travelers. We thoroughly enjoyed our stay and look forward to returning next summer!"
Fairy Tale Guest Cottage in Magic Garden by Pool
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, (54)
"Beautiful property and Michael and Rosealind are some the nicest hosts we have ever encountered. "
The price is €798
includes taxes & fees
21 May - 22 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 €655
includes taxes & fees
21 May - 22 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
Outdoor pool
Sag Harbor Inn
3.5 star property
9.4 out of 10, Exceptional, (422)
"Kind and clean "
The price is €247
includes taxes & fees
19 May - 20 May
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 €673
includes taxes & fees
23 May - 24 May
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 €262
includes taxes & fees
19 May - 20 May
Colonial Shores Resort
View from property
House on Chase Creek
2.5 star property
9.4 out of 10, Exceptional, (64)
"543y"
The price is €289
includes taxes & fees
20 May - 21 May
House on Chase Creek
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 €418
includes taxes & fees
19 May - 20 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 €133
includes taxes & fees
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 €212
includes taxes & fees
20 May - 21 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 €358
includes taxes & fees
22 May - 23 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 €339
includes taxes & fees
29 May - 30 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 €519
includes taxes & fees
21 May - 22 May
Mill House Inn
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See all available properties in Shelter Island
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.

Where to stay in Shelter Island

Find the best Shelter Island areas and neighborhoods for the activities you enjoy most. Learn more about Shelter Island
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Menantic Creek

While there might not be top attractions in Menantic Creek, you can explore the larger area and discover places like Sunset Beach and Crescent Beach.

Find hotels in Menantic Creek

More cheap stays in Shelter Island

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

100 Essex Rd, Old Saybrook, CT
The price is €98 per night from May 22 to May 23
€98
per night
22 May - 23 May
7.4/10 Good! (957 reviews)

Near an Attraction

Image for Gardiner's Bay Country Club

Gardiner's Bay Country Club

Enjoy a round of golf in Shelter Island at Gardiner's Bay Country Club. Stroll along the area's waterfront or simply enjoy its wineries.

See properties
Gardiner's Bay Country Club

Shelter Island hotels information

Number of reviews
2,680
Accommodation
4,787 hotels
Lowest Price
€98
Highest Price
€1,155

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.

Recent Reviews in Shelter Island
Expedia verified reviews

Sag Harbor Inn

Sag Harbor Inn

5/5 Excellent
"Kind and clean "
A verified traveller stayed at Sag Harbor Inn
Posted 1 day ago
Sag Harbor Inn