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
$140 nightly
The price is $160 total per night from Apr 27 to Apr 28
$160 total
Apr 27 - Apr 28
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 ...
Fridge and microwave, coffe

Reviewed on Apr 19, 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 21 to Apr 22
$257 total
Apr 21 - Apr 22
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 ...
We had a nice stay in room 106. Unfortunately, we asked for a wakeup call. The front desk crew went to room 107. The breakfast was quite extensive, and we had a good meal before we left. We would stay there again.

Reviewed on Apr 19, 2026

Opens in a new windowSag Harbor Inn
Offshore Montauk

Offshore Montauk

2 out of 5
71 S Emerson Ave Montauk NY
$258 nightly
The price is $295 total per night from Apr 30 to May 1
$295 total
Apr 30 - May 1
Total with taxes and fees
This hotel features an outdoor pool and a gym. Enjoy the steam room and perks like free self parking and free WiFi. Express check-out and luggage storage are ...
This hotel was very convenient, comfortable, and clean. It is right by the beach and close to restaurants and a market. Also pet friendly. I am glad I stayed here.

Reviewed on Apr 19, 2026

Opens in a new windowOffshore Montauk
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 21 to Apr 22
$192 total
Apr 21 - Apr 22
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 ...
We stayed in a 1 bedroom deluxe loft. Only downfall is how much and how loud the noise travels throughout the unit. Next stay will definitely be a 2 bedroom.

Reviewed on Apr 17, 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
$294 nightly
The price is $338 total per night from Apr 22 to Apr 23
$338 total
Apr 22 - Apr 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 ...
pleasant visit staff very friendly

Reviewed on Apr 16, 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
$223 nightly
The price is $255 total per night from Apr 26 to Apr 27
$255 total
Apr 26 - Apr 27
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 ...
Really nice property!

Reviewed on Apr 16, 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 21 to Apr 22
$319 total
Apr 21 - Apr 22
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 ...
Great stay.

Reviewed on Apr 16, 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
$541 nightly
The price is $618 total per night from Apr 21 to Apr 22
$618 total
Apr 21 - Apr 22
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
$244 nightly
The price is $279 total per night from May 3 to May 4
$279 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 ...
View is stunning but rooms feel dated. Bathroom is extremely tiny and terrace had uncomfortable furniture.

Reviewed on Apr 18, 2026

Opens in a new windowSound View Greenport
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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 $160. 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 4,737 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.

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