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
$164 nightly
The price is $187 total per night from Apr 30 to May 1
$187 total
Apr 30 - May 1
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 ...
Excellent highly recommend

Reviewed on Apr 25, 2026

Opens in a new windowThe Bentley Hotel Southampton
Sag Harbor Inn

Sag Harbor Inn

3.5 out of 5
45 West Water Street Sag Harbor NY
$225 nightly
The price is $257 total per night from Apr 29 to Apr 30
$257 total
Apr 29 - Apr 30
Total with taxes and fees
An outdoor pool is featured at this hotel, along with free self parking. Enjoy the free continental breakfast each morning. A fireplace in the lobby and luggage ...
Clean room and easy parking

Reviewed on Apr 21, 2026

Opens in a new windowSag Harbor Inn
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
$168 nightly
The price is $192 total per night from Apr 27 to Apr 28
$192 total
Apr 27 - Apr 28
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 ...
The Montauk Manor is a beautiful charming

Reviewed on Apr 26, 2026

Opens in a new windowMontauk Manor
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
$264 nightly
The price is $304 total per night from May 20 to May 21
$304 total
May 20 - May 21
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 ...
Was very nice used hotels.com saved alot for both rooms. Enkoyed the pool and spa hot tub was great. Pricy but worth it the view was beautiful

Reviewed on Apr 25, 2026

Opens in a new windowWater's Edge Resort & Spa
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St Greenport NY
$224 nightly
The price is $256 total per night from Apr 28 to Apr 29
$256 total
Apr 28 - Apr 29
Total with taxes and fees
This hotel features a 24-hour gym and a seasonal outdoor pool. Business travelers can take advantage of the free WiFi in public areas. Enjoy the free continental ...
Great

Reviewed on Apr 23, 2026

Opens in a new windowThe Harbor Front Inn
Montauk Yacht Club

Montauk Yacht Club

4 out of 5
32 Star Island Rd Montauk NY
$279 nightly
The price is $319 total per night from Apr 27 to Apr 28
$319 total
Apr 27 - Apr 28
Total with taxes and fees
This hotel features a private beach, a marina, and 2 restaurants. Traveling on business? Take advantage of the 5 conference rooms, along with free WiFi in public ...
The Montauk Yacht Club is a beautiful and relaxing getaway with a true coastal luxury feel. The property is well-maintained, with scenic waterfront views that make the entire experience feel special and refreshing. The rooms are comfortable and thoughtfully designed, offering a clean and modern aesthetic. ...

Reviewed on Apr 21, 2026

Opens in a new windowMontauk Yacht Club
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
$478 nightly
The price is $546 total per night from May 10 to May 11
$546 total
May 10 - May 11
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 ...
I checked in during a severe snowstorm and had to leave the hotel within 30 minutes due to the conditions. Despite barely using the room, I was charged $304.50 as a “service fee.” I later reached out to the hotel to request clarification and a possible adjustment, but I have not received any response ...

Reviewed on Apr 20, 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
$252 nightly
The price is $288 total per night from May 3 to May 4
$288 total
May 3 - May 4
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 ...
This is a lovely motel located right on the Sound and all rooms face the water. The room was clean and relatively spacious, though most of the space was devoted to the kitchen and living areas. The bathroom was a bit small, as was the sleeping area. My family, including an elderly relative, traveled ...

Reviewed on Apr 21, 2026

Opens in a new windowSound View Greenport
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
100 Essex Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $130 total per night from Apr 28 to Apr 29
$130 total
Apr 28 - Apr 29
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will ...
I was first placed in a dirty room but they were very quick and efficient to move me which was great b/c I don’t like first floor rooms. In my second room on 2nd floor the window lock was broken so I couldn’t lock it. Uncomfortable but being in 2nd floor helped. Clock in the room nor working or unplugged?? ...

Reviewed on Apr 20, 2026

Opens in a new windowQuality Inn Old Saybrook - Westbrook
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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 $130. 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 4,761 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

Montauk Manor

Montauk Manor

5 out of 5
Posted 5 hours ago
Travelocity Verified Review
"The Montauk Manor is a beautiful charming"
A verified traveler stayed at Montauk Manor
Montauk Manor

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