Find hotels in Shelter Island, NY from $89

Check Shelter Island hotel prices

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May 29 - May 30
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May 30 - May 31
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May 31 - Jun 2
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Jun 7 - Jun 9

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Compare 4,820 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Terrace/patio
Capri
3.5 star property
6.4 out of 10, (220)
"Loved it!"
The price is $359
$435 total
includes taxes & fees
Jun 2 - Jun 3
Capri
Front of property
The Wainscott Inn
3.0 star property
8.6 out of 10, Excellent, (93)
"The staff is wonderful and the rooms are nicely decorated. The hotel is going through a renovation so is not very presentable for now but should be all fixed bt July 1st. "
The price is $234
$302 total
includes taxes & fees
May 30 - May 31
The Wainscott Inn
Seasonal outdoor pool, pool umbrellas, sun loungers
The Pridwin Hotel
3.0 star property
10.0 out of 10, Exceptional, (21)
"Excellent Service"
The price is $296
$372 total
includes taxes & fees
May 30 - May 31
The Pridwin Hotel
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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 $762
$869 total
includes taxes & fees
May 30 - May 31
East Hampton Art House Bed & Breakfast
Cottage, 1 Bedroom (with porch - Pet Friendly + Fee) | Private kitchen | Dishwasher, coffee/tea maker
Hampton's Vacation Inn
2.5 star property
9.0 out of 10, Wonderful, (235)
"This was a very nice cottage in a great location. Very clean and spacious. Comfortable bed. Staff very helpful. Nice pool. Only issue was the tennis court was not available for our stay. They began power washing it after we arrived (after I texted about it when we arrived) and said it would be available at 1pm the next day. We had to check out at 10:30 that day. "
The price is $295
$337 total
includes taxes & fees
Jun 24 - Jun 25
Hampton's Vacation Inn
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 $321
$388 total
includes taxes & fees
Jun 13 - Jun 14
East Hampton House Resort
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, (375)
"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 $207
$246 total
includes taxes & fees
May 30 - May 31
Bayview Resort
Exterior
Journey East Hampton
4.0 star property
8.8 out of 10, Excellent, (89)
"Loved the room, bed was comfortable, shower was lovely. Cindy gave great suggestions on where to go."
The price is $325
$408 total
includes taxes & fees
May 30 - May 31
Journey East Hampton
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, (27)
"The room was beautiful.The grounds were amazing."
The price is $550
$659 total
includes taxes & fees
Jun 2 - Jun 3
Canoe Place Inn and Cottages
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 $595
$713 total
includes taxes & fees
Jun 2 - Jun 3
The Roundtree, Amagansett
Front of property - evening/night
Mill House Inn
5.0 star property
8.8 out of 10, Excellent, (51)
"Excellent facility and excellent service. Highly recommend. "
The price is $475
$542 total
includes taxes & fees
Jun 2 - Jun 3
Mill House Inn
Front of property - evening/night
The Maidstone
4.0 star property
7.8 out of 10, Good, (112)
"Staff was very friendly and engaging. Handled all of our needs wonderfully."
The Maidstone
Property grounds
Hampton Maid Motel
2.5 star property
8.8 out of 10, Excellent, (524)
"Always excellent. Property, staff and food are outstanding."
The price is $280
$320 total
includes taxes & fees
Jun 3 - Jun 4
Hampton Maid Motel
Aerial view
Colonial Shores Resort
2.5 star property
9.4 out of 10, Exceptional, (83)
"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 $260
$297 total
includes taxes & fees
May 30 - May 31
Colonial Shores Resort
2 restaurants, breakfast, lunch, dinner served; Mediterranean cuisine
EHP Resort & Marina
3.5 star property
7.8 out of 10, Good, (7)
"Beautiful property and the cottages were clean, gorgeous, and comfortable. It was just hard to get in touch with anyone for service related issues. The restaurant on site, Si Si was amazing and the staff there went above and beyond!"
The price is $429
$538 total
includes taxes & fees
May 30 - May 31
EHP Resort & Marina
View from property
House on Chase Creek
2.5 star property
9.4 out of 10, Exceptional, (64)
"Amazing location. Lovely lake. Serene and Tranquil experience. "
The price is $276
$315 total
includes taxes & fees
Jun 3 - Jun 4
House on Chase Creek
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
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 $450
$514 total
includes taxes & fees
May 30 - May 31
Southampton Village Motel
Deluxe Suite | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds
The Reform Club
2.0 star property
The price is $1,299
$1,661 total
includes taxes & fees
Jun 3 - Jun 4
The Reform Club
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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

If you're looking for some top things to see and do in Menantic Creek and surrounding area, you can visit Sunset Beach and Shelter Island Country Club.

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 $101 per night from Jun 5 to Jun 6
$101
$116 total
includes taxes & fees
Jun 5 - Jun 6
7.4/10 Good! (963 reviews)

Stay near popular Shelter Island attractions

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.

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Gardiner's Bay Country Club

Shelter Island Travel Info

Number of reviews
2,795
Accommodation
4,820 hotels
Highest price
$1,299
Lowest price
$89

Frequently asked questions

Where is the best place to stay in Shelter Island?

Located 18.4 mi (29.7 km) from the heart of Shelter Island, Gurney's Montauk Resort & Seawater Spa is a top choice for your stay based on our traveler data. Other good choices for your trip to the area are Pier Blue Inn Old Saybrook - Essex and Montauk Manor. See all available top hotels, or vacation rentals in Shelter Island.

What's the top vacation rental that Shelter Island has to offer?

Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool: Visitors like this Shelter Island vacation home rental. It offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation. See all 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's the best place to stay near the beach in Shelter Island?

Sunset Beach Hotel is a top beachfront accommodation located on Sunset Beach. See more stays near the beach in Shelter Island.

What are some accommodations with pools in Shelter Island?

Gurney's Montauk Resort & Seawater Spa: Resort, 13-minute walk from The Hamptons Beaches. Features a seasonal outdoor pool, an indoor pool, and a private beach. Montauk Manor and The Bentley Hotel Southampton are a couple of other choices that feature an onsite pool. View all hotels with pools in Shelter Island.

What is the best spa hotel in Shelter Island?

Waterfront House With Dock And Private Beach

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 100 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.

Recent reviews of Shelter Island hotels
Expedia verified reviews

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

5/5 Excellent
"It was a gem finding this property during our last minute memorial wknd . Booking . Expected goes above and beyond.luxury Property, amazing staff’s great restaurants & bars with amenities, friendly guests , we've met some guest also from NY extended stay due to fog issue in marina instead we enjoyed bonding at Cho Cho lounge on their Monday trivia . Jeff in that bar does a fantastic drinks ! Fresh Seafood meals we enjoyed as well facing marina . "
A verified traveler from Bayside stayed at Saybrook Point Resort & Marina
Posted 13 hours ago
Saybrook Point Resort & Marina