Find hotels in Shelter Island, NY from ￥14,056

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Oct 24 - Oct 25
Tomorrow
Oct 25 - Oct 26
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Oct 24 - Oct 26
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Oct 31 - Nov 2

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Compare 4,707 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Front of property - evening/night
Montauk Manor
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1257)
"Beautiful grounds, excellent staff"
United States
Jess
The price is ￥23,072
￥29,350 total
includes taxes & fees
Nov 3 - Nov 4
Montauk Manor
Outdoor wedding area
Gurney's Montauk Resort & Seawater Spa
Gurney's Montauk Resort & Seawater Spa
4.0 star property
8.2 out of 10, Very Good, (675)
"Amazing resort, very friendly staff, food and drinks are Amazing! We enjoyed our stay. "
United States
Amandip
The price is ￥42,178
￥57,565 total
includes taxes & fees
Nov 24 - Nov 25
Gurney's Montauk Resort & Seawater Spa
Exterior
Saybrook Point Resort & Marina
Saybrook Point Resort & Marina
3.5 star property
9.4 out of 10, Exceptional, (1003)
"Beautiful property, we loved our room, friendly staff. "
United States
Natalie
The price is ￥36,644
￥45,955 total
includes taxes & fees
Nov 6 - Nov 7
Saybrook Point Resort & Marina
Outdoor pool
The Atlantic Hotel
The Atlantic Hotel
2.5 star property
7.2 out of 10, Good, (958)
"Love the area love the room size clean parking was perfect "
United States
Sherwood
The Atlantic Hotel
Deluxe Double Room, 1 King Bed, City View | In-room safe, individually decorated, individually furnished, desk
Hampton Bays Hotel on Main
Hampton Bays Hotel on Main
2.0 star property
7.0 out of 10, Good, (65)
"Needed a last minute place to stay and this was PERFECT!! Reasonably priced and the owner is lovely. The rooms have everything you need and there’s a bar on the property where you can play pool and have an after-dinner drink. Highly recommend!"
United States
Olivia
Hampton Bays Hotel on Main
Seasonal outdoor pool, pool umbrellas, sun loungers
Marram
Marram
4.0 star property
8.8 out of 10, Excellent, (238)
"It was an amazing relaxing weekend. We want to come back next year the same weekend!"
United States
Piera
The price is ￥30,281
￥48,543 total
includes taxes & fees
Nov 16 - Nov 17
Marram
Property grounds
Pier Blue Inn Old Saybrook - Essex
Pier Blue Inn Old Saybrook - Essex
2.0 star property
8.0 out of 10, Very Good, (1001)
"Staff was incredibly communicative, kind, and patient. Definitely recommend and we would stay again!"
United States
Laura
The price is ￥12,222
￥14,056 total
includes taxes & fees
Oct 26 - Oct 27
Pier Blue Inn Old Saybrook - Essex
View from property
Ocean Surf Resort
Ocean Surf Resort
2.0 star property
8.4 out of 10, Very Good, (221)
"Everything was great "
United States
Darryl
The price is ￥38,216
￥43,662 total
includes taxes & fees
Oct 25 - Oct 26
Ocean Surf Resort
Exterior
Water's Edge Resort & Spa
Water's Edge Resort & Spa
3.5 star property
8.8 out of 10, Excellent, (1009)
"We love the stay everything was perfect"
United States
angelica
The price is ￥33,197
￥40,809 total
includes taxes & fees
Oct 31 - Nov 1
Water's Edge Resort & Spa
One Bedroom Harbor View Terrace Suite | View from room
The Harbor Front Inn
The Harbor Front Inn
3.5 star property
8.8 out of 10, Excellent, (524)
"Great location ,beautiful hotel,nice staff"
United States
ROBERT
The price is ￥25,695
￥36,790 total
includes taxes & fees
Nov 23 - Nov 24
The Harbor Front Inn
Property grounds
The Hampton Maid
The Hampton Maid
2.5 star property
9.0 out of 10, Wonderful, (673)
"Love this place "
United States
Diane
The Hampton Maid
Indoor pool, open 9:00 AM to 9:00 PM, sun loungers
Quality Inn Old Saybrook - Westbrook
Quality Inn Old Saybrook - Westbrook
2.5 star property
7.8 out of 10, Good, (1002)
"Breakfast was bomb"
United States
Jostiena
The price is ￥14,204
￥16,335 total
includes taxes & fees
Nov 12 - Nov 13
Quality Inn Old Saybrook - Westbrook
Exterior
Zey Hotel
Zey Hotel
3.5 star property
9.2 out of 10, Wonderful, (280)
"Clean and quiet right on a main street with plenty of shopping and dining. Very close to the vineyards. Great stay."
United States
Alexandra
Zey Hotel
View from room
Offshore Montauk
Offshore Montauk
2.0 star property
9.4 out of 10, Exceptional, (62)
"Great place "
United States
Kevin
The price is ￥22,746
￥43,421 total
includes taxes & fees
Nov 9 - Nov 10
Offshore Montauk
King Ocean Front | Balcony view
Montauk Blue Hotel
Montauk Blue Hotel
2.0 star property
9.2 out of 10, Wonderful, (169)
"The beach view is spectacular the surrounding area has everything you need for a each getaway"
United States
Jason
The price is ￥18,158
￥20,746 total
includes taxes & fees
Nov 9 - Nov 10
Montauk Blue Hotel
View from property
Ocean Vista Resort
Ocean Vista Resort
2.5 star property
9.0 out of 10, Wonderful, (197)
"Such a beautiful place to stay. Pam at the front was so nice and welcoming. The room was clean it was quiet and everyone was friendly. Love that it has a private beach! Would 10/10 recommend it and deff will be going back."
United States
kayla c
Ocean Vista Resort
Exterior
Madison Beach Hotel
Madison Beach Hotel
4.0 star property
9.4 out of 10, Exceptional, (324)
"the staff was exceptional and our dinner was very good"
United States
john
The price is ￥37,412
￥43,023 total
includes taxes & fees
Oct 30 - Oct 31
Madison Beach Hotel
Front of property
The Preston House & Hotel
The Preston House & Hotel
3.5 star property
9.8 out of 10, Exceptional, (366)
"Staff was amazing, include the restaurants’ staff! 2nd time staying there, will be back for many more!"
United States
Nakia
The price is ￥30,651
￥35,019 total
includes taxes & fees
Nov 23 - Nov 24
The Preston House & Hotel
Indoor pool, 2 outdoor pools
Montauk Yacht Club
Montauk Yacht Club
4.0 star property
8.6 out of 10, Excellent, (1005)
"Wonderful hotel and location "
United States
FIONA
Montauk Yacht Club
Apartment, 2 Bedrooms | Private kitchen | Microwave, coffee/tea maker, cookware/dishes/utensils
Hampton's Vacation Inn
Hampton's Vacation Inn
2.5 star property
9.0 out of 10, Wonderful, (321)
"A great Hampton location that's less than a thirty minutes drive from Coopers Beach and South Hampton main street."
United States
Maggie
The price is ￥29,526
￥33,734 total
includes taxes & fees
Oct 26 - Oct 27
Hampton's Vacation Inn
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

Coecles Harbor

When in Coecles Harbor, you can plan a visit to Gardiner's Bay Country Club and Mashomack Preserve, 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.

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 Crescent Beach and Sunset Beach.

Shorewood

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

Stay near popular Shelter Island attractions

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

Shelter Island Whale's Tail

You can take time to visit Shelter Island Whale's Tail during your travels to Shelter Island. Wander the beaches and waterfront in the area.
See properties

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.

See all hotels in Shelter Island
Central Park summer

Top Shelter Island Hotel Reviews

The Sagaponack

The Sagaponack

10/10 Excellent
"The room was spotless and had everything that you would need. Would stay here again."
Marjorie 1-night trip
Posted 5 days ago
The Sagaponack

More cheap stays in Shelter Island

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd, Old Saybrook, CT
The price is ￥12,222 per night from Oct 26 to Oct 27
￥12,222
￥14,056 total
Oct 26 - Oct 27
includes taxes & fees
7.8/10 Good! (1,000 reviews)

Frequently asked questions

Where is the best place to stay in Shelter Island?
Located 15.5 mi (24.9 km) from the heart of Shelter Island, Pier Blue Inn Old Saybrook - Essex 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 Blue Hotel. See all available top hotels, or vacation rentals in Shelter Island.
What's the top vacation rental that Shelter Island has to offer?
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor: 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 patio, a garden, and a hot tub 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.
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: Resort, 13-minute walk from The Hamptons Beaches. Offers a seasonal outdoor pool, an indoor pool, and a private beach. Montauk Blue Hotel and Marram 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 95 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 Mashomack Preserve. 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.

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