Book Hotels in Shelter Island, NY

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Top Shelter Island hotels

The Bentley Hotel Southampton

The Bentley Hotel Southampton

2 out of 5
161 Hills Station Rd Southampton NY
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $145 total per night from Feb 25 to Feb 26
$145 total
Feb 25 - Feb 26
Total with taxes and fees
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this hotel. If you want to take your pet along, this pet-friendly property ...
The room was spacious and very clean.The hotel staff was very courteous and took care of your needs very quickly. Definitely will come back.

Reviewed on Feb 18, 2026

Opens in a new windowThe Bentley Hotel Southampton
Offshore Montauk

Offshore Montauk

2 out of 5
71 S Emerson Ave Montauk NY
$166 nightly
The price is $190 total per night from Mar 3 to Mar 4
$190 total
Mar 3 - Mar 4
Total with taxes and fees
An outdoor pool is featured at this hotel, along with free self parking. WiFi in public areas is free. A picnic area is also provided.
The room was very clean & had a nice view of the dunes & ocean. The best part was the comfy bed & pillows. It was easy to walk to restaurants & shops in town. We had a great time in Montauk!!

Reviewed on Feb 17, 2026

Opens in a new windowOffshore Montauk
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
$133 nightly
The price is $152 total per night from Mar 11 to Mar 12
$152 total
Mar 11 - Mar 12
Total with taxes and fees
3 outdoor tennis courts, an indoor pool, and a 24-hour gym are all featured at this smoke-free aparthotel. Enjoy the seasonal outdoor pool and perks like free ...
Room was very nice

Reviewed on Feb 17, 2026

Opens in a new windowMontauk Manor
Montauk Blue Hotel

Montauk Blue Hotel

2 out of 5
108 South Emerson Avenue Montauk NY
This hotel features an indoor pool and a hot tub. WiFi in public areas is free. Self parking, a terrace, and a picnic area are also offered.
Great view of sunrise and sunset

Reviewed on Jan 19, 2026

Get rates
Opens in a new windowMontauk Blue Hotel
Hyatt Place Long Island East End

Hyatt Place Long Island East End

3 out of 5
451 East Main Street Riverhead NY
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $135 total per night from Mar 2 to Mar 3
$135 total
Mar 2 - Mar 3
Total with taxes and fees
A marina, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and ...
Great view from the room. Nice, quiet and clean.

Reviewed on Feb 18, 2026

Opens in a new windowHyatt Place Long Island East End
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
$244 nightly
The price is $281 total per night from Feb 22 to Feb 23
$281 total
Feb 22 - Feb 23
Total with taxes and fees
This smoke-free resort features a private beach, a full-service spa, and 3 restaurants. Relax with beach cabanas and sun loungers, and cool off with a drink ...
The view of the ocean and gazebos were amazing. Everyone was so courteous and it wasn't a madhouse. Quiet and relaxing. The pool was also nice and warm

Reviewed on Feb 18, 2026

Opens in a new windowWater's Edge Resort & Spa
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
$344 nightly
The price is $393 total per night from Feb 22 to Feb 23
$393 total
Feb 22 - Feb 23
Total with taxes and fees
This resort features a private beach, a full-service spa, and 2 restaurants. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside ...
The room Was ready early and spotless The stuffy lobsters for the girls was a nice touch

Reviewed on Feb 16, 2026

Opens in a new windowGurney's Montauk Resort & Seawater Spa
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
$173 nightly
The price is $197 total per night from Mar 4 to Mar 5
$197 total
Mar 4 - Mar 5
Total with taxes and fees
A private beach and a restaurant are featured at this smoke-free hotel. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Unwind with ...
Hotel complaints Extra unknown/ non-disclosed charges- 13 arrival and 15 checkout **there are more charges than shown in Expedia Rooms not matching pictures (told to have an ocean view when not the case) Some ice on road/ sidewalk (seen someone slip) Disappointing “continental” breakfast Parking ...

Reviewed on Feb 15, 2026

Opens in a new windowSound View Greenport
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $91 total per night from Feb 22 to Feb 23
$91 total
Feb 22 - Feb 23
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers ...
Very nice check in and check out Room refurbished/clean and comfortable Would stay again

Reviewed on Feb 16, 2026

Opens in a new windowPier Blue Inn Old Saybrook - Essex
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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.

Frequently asked questions

What are the top kid-friendly hotels in Shelter Island?
From carefully considered amenities to rooms with bunk beds, kid-friendly hotels come with features that can help transform a routine family vacation into an extraordinary one. These Shelter Island properties make getting away with children a breeze: You'll be well looked after at Beautifully renovated Farmhouse sitting on a lush property. It comes with a nearby beach, a travel crib and a flair for making families feel at home. Alternatively, spend your Shelter Island getaway at Paradise found on Shelter Island. Make the most of a playground, a nearby beach and more here.
Where can I find cheap hotels in Shelter Island?
At Travelocity you'll find really nice hotels in Shelter Island at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Shelter Island rather than in Shelter Island. We may find you even better rates, too.
How do I find the best Shelter Island hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Shelter Island then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Shelter Island?
The cheapest hotel in Shelter Island is $91. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Shelter Island?
There are 4,702 hotels in Shelter Island on Travelocity.
What are the best hotels in Shelter Island?
Shelter Island has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Shelter Island for you!
When is the best time to visit Shelter Island?
If you want the joy of a fun-filled trip in peak season, visit Shelter Island during May, June and July. If you'd prefer the peace of off-season, book a stay during quieter months, such as January, October and December.
When is the cheapest time to stay in Shelter Island?
Based on historic data is usually the cheapest month to visit Shelter Island. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Shelter Island?
There are multiple hotels in Shelter Island that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Shelter Island. We have plenty of kid-friendly hotels in Shelter Island to choose from on Travelocity!
Why book a hotel in Shelter Island through Travelocity?
Because we have the top hotels in Shelter Island! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Shelter Island on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Shelter Island hotel reviews by fellow wanderers

Water's Edge Resort & Spa

Water's Edge Resort & Spa

5 out of 5
Posted 5 hours ago
Travelocity Verified Review
"The view of the ocean and gazebos were amazing. Everyone was so courteous and it wasn't a madhouse. Quiet and relaxing. The pool was also nice and warm"
A verified traveler stayed at Water's Edge Resort & Spa
Water's Edge Resort & Spa

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