Find hotels in Shelter Island, NY from ￥13,902

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Oct 16 - Oct 17
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Oct 17 - Oct 18
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Oct 17 - Oct 19
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Oct 24 - Oct 26

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Compare 4,730 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, (1254)
"Beautiful grounds, excellent staff"
The price is ￥30,559
￥37,869 total
includes taxes & fees
Nov 7 - Nov 8
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, (671)
"Amazing resort, very friendly staff, food and drinks are Amazing! We enjoyed our stay. "
The price is ￥39,789
￥54,305 total
includes taxes & fees
Nov 4 - Nov 5
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, (1012)
"Beautiful property, we loved our room, friendly staff. "
The price is ￥36,241
￥45,450 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, (955)
"Love the area love the room size clean parking was perfect "
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!"
Hampton Bays Hotel on Main
Seasonal outdoor pool, pool umbrellas, sun loungers
Marram
Marram
4.0 star property
8.8 out of 10, Excellent, (235)
"It was an amazing relaxing weekend. We want to come back next year the same weekend!"
The price is ￥29,347
￥47,322 total
includes taxes & fees
Oct 29 - Oct 30
Marram
Seasonal outdoor pool
Beachcomber Resort at Montauk
Beachcomber Resort at Montauk
3.0 star property
9.4 out of 10, Exceptional, (607)
"Lovely stay and great staff! "
Beachcomber Resort at Montauk
Property grounds
Pier Blue Inn Old Saybrook - Essex
Pier Blue Inn Old Saybrook - Essex
2.0 star property
7.8 out of 10, Good, (1014)
"Staff was incredibly communicative, kind, and patient. Definitely recommend and we would stay again!"
The price is ￥12,088
￥13,902 total
includes taxes & fees
Oct 19 - Oct 20
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, (217)
"Beach view "
The price is ￥18,931
￥21,630 total
includes taxes & fees
Oct 19 - Oct 20
Ocean Surf Resort
View from room
Offshore Montauk
Offshore Montauk
2.0 star property
9.2 out of 10, Wonderful, (59)
"Great place "
The price is ￥22,723
￥43,204 total
includes taxes & fees
Oct 30 - Oct 31
Offshore Montauk
Exterior
Water's Edge Resort & Spa
Water's Edge Resort & Spa
3.5 star property
8.8 out of 10, Excellent, (1008)
"We love the stay everything was perfect"
The price is ￥30,910
￥38,150 total
includes taxes & fees
Oct 19 - Oct 20
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, (523)
"Great location ,beautiful hotel,nice staff"
The price is ￥24,926
￥35,864 total
includes taxes & fees
Nov 2 - Nov 3
The Harbor Front Inn
Exterior
Zey Hotel
Zey Hotel
3.5 star property
9.2 out of 10, Wonderful, (279)
"Clean and quiet right on a main street with plenty of shopping and dining. Very close to the vineyards. Great stay."
Zey Hotel
Property grounds
The Hampton Maid
The Hampton Maid
2.5 star property
9.0 out of 10, Wonderful, (671)
"Love this place "
The price is ￥42,783
￥48,881 total
includes taxes & fees
Oct 17 - Oct 18
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
7.6 out of 10, Good, (1009)
"We have stayed there before so have been pleased with it."
The price is ￥14,110
￥16,227 total
includes taxes & fees
Nov 2 - Nov 3
Quality Inn Old Saybrook - Westbrook
View from property
Ocean Vista Resort
Ocean Vista Resort
2.5 star property
9.0 out of 10, Wonderful, (196)
"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."
Ocean Vista Resort
King Ocean Front | Balcony view
Montauk Blue Hotel
Montauk Blue Hotel
2.0 star property
9.2 out of 10, Wonderful, (161)
"The beach view is spectacular the surrounding area has everything you need for a each getaway"
The price is ￥17,600
￥20,108 total
includes taxes & fees
Nov 9 - Nov 10
Montauk Blue Hotel
Exterior
Madison Beach Hotel
Madison Beach Hotel
4.0 star property
9.4 out of 10, Exceptional, (323)
"the staff was exceptional and our dinner was very good"
The price is ￥37,000
￥42,550 total
includes taxes & fees
Oct 30 - Oct 31
Madison Beach Hotel
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, (318)
"A great Hampton location that's less than a thirty minutes drive from Coopers Beach and South Hampton main street."
The price is ￥19,015
￥21,724 total
includes taxes & fees
Oct 19 - Oct 20
Hampton's Vacation Inn
Front of property
The Preston House & Hotel
The Preston House & Hotel
3.5 star property
9.8 out of 10, Exceptional, (366)
"Everything about the Preston House was great the staff are amazing and they were so helpful throughout the booking and stay! "
The price is ￥30,792
￥35,179 total
includes taxes & fees
Nov 9 - Nov 10
The Preston House & Hotel
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 Crescent Beach and Sunset Beach.

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.

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 Sunset Beach and Crescent Beach.

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.
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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.
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Learn more about Shelter Island

Escape to Shelter Island! Enjoy its island views, natural setting, and beaches.

See all hotels in Shelter Island
Great shot of Sunset Beach on Shelter Island from our boat, before heading closer to anchor and swim in. A beautiful little slice of Southern France right here on Long Island Sound! If you get a chance, definitely check this place out.
Photo by tom owens
Open Photo by tom owens

Top Shelter Island Hotel Reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"We love the stay everything was perfect"
angelica 1-night trip
Posted 2 days ago
Water's Edge Resort & Spa

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 ￥12,088 per night from Oct 19 to Oct 20
￥12,088
￥13,902 total
Oct 19 - Oct 20
includes taxes & fees
7.8/10 Good! (1,009 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 Quality Inn Old Saybrook - Westbrook. See all available top hotels, or vacation rentals in Shelter Island.
What's the top vacation rental that Shelter Island has to offer?
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available: Visitors like this Shelter Island vacation home rental. It is located near the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, 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.
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: Offers a seasonal outdoor pool, an indoor pool, and a private beach. Quality Inn Old Saybrook - Westbrook and Montauk Blue Hotel 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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