Find hotels in Shelter Island, NY from ¥11,792

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Our top choices for Shelter Island hotels

The Captain Stannard

The Captain Stannard
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (259)
"The Inn and staff were warm and welcoming, the facility exceptionally clean. Breakfast exceeded my expectations for a continental breakfast! Would absolutely stay again! "
United States
Lisa
The Captain Stannard

Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (176)
"Charming, beautiful inn; excellent food and service."
United States
Michael
The price is ¥33,612
¥37,309 total
includes taxes & fees
Dec 22 - Dec 23
Westbrook Inn B&B

Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook
2.0 star property
Old Saybrook
7.2 out of 10, Good, (461)
"A very clean and convenient hotel. It’s close to the beach and provides a parking pass for local beach with a refundable deposit."
United States
Anonymous traveler
The price is ¥10,574
¥12,160 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Econo Lodge Inn & Suites Old Saybrook Westbrook

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (298)
"Great staff and clean rooms"
United States
Tyler
The price is ¥12,305
¥14,151 total
includes taxes & fees
Dec 22 - Dec 23
Clinton Motel

Vine & Sand

Vine & Sand
3.0 star property
Southold
9.6 out of 10, Exceptional, (13)
"This B&B, and its hosts, were simply amazing. I cannot recommend this place enough."
United States
Sandra
Vine & Sand

Water's Edge Resort & Spa

Water's Edge Resort & Spa
3.5 star property
Westbrook Center
8.8 out of 10, Excellent, (1001)
"Everything was wonderful. Staff was friendly, very clean,we enjoyed it."
United States
Donna
The price is ¥28,725
¥35,755 total
includes taxes & fees
Dec 22 - Dec 23
Water's Edge Resort & Spa

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1001)
"The staff was friendly. The room was good. "
United States
Narida
The price is ¥15,956
¥18,349 total
includes taxes & fees
Dec 28 - Dec 29
Quality Inn Old Saybrook - Westbrook

Super 8 by Wyndham Old Saybrook

Super 8 by Wyndham Old Saybrook
2.0 star property
Old Saybrook
7.0 out of 10, Good, (908)
"A simple, affordable, conveniently located, and pleasant stay."
United States
Jason
The price is ¥12,636
¥14,967 total
includes taxes & fees
Dec 22 - Dec 23
Super 8 by Wyndham Old Saybrook

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina
3.5 star property
Old Saybrook Center
9.6 out of 10, Exceptional, (1001)
"Wonderful stay in a beautiful setting."
United States
Deborah
The price is ¥46,309
¥57,200 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Saybrook Point Resort & Marina

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
2.0 star property
Saybrook Manor
8.0 out of 10, Very Good, (1005)
"Staff was courteous, and bed was comfortable. The room hasn't had decor updated for decades. Fine for an overnight if you are just traveling through area for the price. "
United States
sue
Pier Blue Inn Old Saybrook - Essex

Harpoon House

Harpoon House
3.0 star property
Southampton
8.4 out of 10, Very Good, (148)
"Very cute location- rooms are very spacious. We were able to walk into town. Would definitely stay again. "
United States
Karissa
Harpoon House

Liberty Inn

Liberty Inn
2.0 star property
Old Saybrook
7.4 out of 10, Good, (640)
"Great little place to stay with friendly staff and clean room"
United States
Carolan
The price is ¥12,636
¥14,531 total
includes taxes & fees
Dec 22 - Dec 23
Liberty Inn

Lamplighter Motel - Clinton, Connecticut

Lamplighter Motel - Clinton, Connecticut
2.5 star property
Clinton
6.4 out of 10, (228)
"Would stay again. "
United States
pamela
The price is ¥10,254
¥11,792 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Lamplighter Motel - Clinton, Connecticut

Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (444)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is ¥15,617
¥20,185 total
includes taxes & fees
Dec 22 - Dec 23
Hamlet Inn

Southampton Long Island Hotel

Southampton Long Island Hotel
2.5 star property
Southampton
8.6 out of 10, Excellent, (203)
"Good location. Nice people!! "
United States
Theresa
The price is ¥18,733
¥22,341 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Southampton Long Island Hotel

Hero Beach Club

Hero Beach Club
4.0 star property
Montauk
9.0 out of 10, Wonderful, (202)
"Great weekend trip "
United States
Timothy
The price is ¥22,579
¥41,837 total
includes taxes & fees
Dec 28 - Dec 29
Hero Beach Club

James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast
4.0 star property
Old Saybrook Center
9.0 out of 10, Wonderful, (23)
"My husband and I stayed here for a quick weekend getaway and loved our experience! The location was perfect - located near restaurants, shops, and the beach - and the room was clean and charming. We will definitely be back!"
United States
Rachel
James Pharmacy Bed & Breakfast

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (401)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
The price is ¥19,739
¥22,710 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Bentley Hotel Southampton

Southampton Inn

Southampton Inn
3.0 star property
Southampton
8.6 out of 10, Excellent, (549)
"Such a great location!"
United States
Elizabeth
The price is ¥31,550
¥38,616 total
includes taxes & fees
Dec 22 - Dec 23
Southampton Inn

Canoe Place Waterfront Residences

Canoe Place Waterfront Residences
4.0 star property
Hampton Bays
10.0 out of 10, Exceptional, (1)
The price is ¥305,270
¥369,697 total
includes taxes & fees
Dec 23 - Dec 24
Canoe Place Waterfront Residences
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.
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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
Learn more about Shelter Island

Silver Beach

While Silver Beach might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Sunset Beach and Crescent Beach.

Coecles Harbor

When in Coecles Harbor, you can plan a visit to Shelter Island Whale's Tail and Gardiner's Bay Country Club, some noteworthy sights in the nearby area.

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 Crescent Beach.

Hay Beach

Hay Beach might not have many top sights, but Gardiner's Bay Country Club and Greenport Carousel are two attractions nearby that you can check out.

Shorewood

While there might not be top attractions in Shorewood, you can explore the larger area and discover places like Mashomack Preserve and Shelter Island Historical Society.

Stay near popular Shelter Island attractions

Learn more about Shelter Island

Nestled between Long Island's forks, this serene island offers pristine beaches and kayaking through Mashomack Preserve's coastal wetlands. Rent bikes to explore historic mansions and stop at Sunset Beach for seafood with spectacular evening views across Shelter Bay.

Central Park summer

Top Shelter Island Hotel Reviews

More cheap stays in Shelter Island

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 Water's Edge Resort & Spa and Pier Blue Inn Old Saybrook - Essex. See all available top hotels, or vacation rentals in Shelter Island.
What's the top vacation rental that Shelter Island has to offer?
Work and Play Special! Extended Stay Discount: This highly rated vacation home rental in Shelter Island is located near the beach and has an outdoor pool, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a garden. 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.
What's the best pet-friendly accommodation in Shelter Island?
Sunset Beach Hotel is a top hotel for people traveling with their pets, and offers a restaurant and free WiFi for its human guests. See more pet-friendly hotel accommodations in Shelter Island.
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 hotel with free WiFi and free parking, and it's 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: Features a seasonal outdoor pool, an indoor pool, and a private beach. Water's Edge Resort & Spa and Sound View Greenport 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 98 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, Mashomack Preserve, and Crescent Beach. A couple of additional sights to add to your agenda are Shelter Island Historical Society and Shelter Island Whale's Tail. 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.

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