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
$144 nightly
The price is $165 total per night from May 20 to May 21
$165 total
May 20 - May 21
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 ...
Great for dogs - huge fenced yard

Reviewed on May 11, 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
$315 nightly
The price is $360 total per night from May 25 to May 26
$360 total
May 25 - May 26
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 ...
Great location, seemed a little outdated for the area. Breakfast was so so, didn't seem fresh. Late check-in was very helpful.

Reviewed on May 10, 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 May 27 to May 28
$192 total
May 27 - May 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 ...
Cute place great views would go back in the summer

Reviewed on May 11, 2026

Opens in a new windowMontauk Manor
Montauk Blue Hotel

Montauk Blue Hotel

2 out of 5
108 South Emerson Avenue Montauk NY
$230 nightly
The price is $263 total per night from May 18 to May 19
$263 total
May 18 - May 19
Total with taxes and fees
This hotel features an indoor pool and a hot tub. A terrace, a picnic area, and luggage storage are also on offer.
Beautiful ocean front room. However, I wasn’t aware I would be charged an extra 35 dollars per day. She said it was a facility fee

Reviewed on May 4, 2026

Opens in a new windowMontauk Blue Hotel
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
$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 ...
Great views from the restaurant and bar area. Staff were very friendly and attentive. Will stay here again.

Reviewed on May 8, 2026

Opens in a new windowWater's Edge Resort & Spa
Montauk Yacht Club

Montauk Yacht Club

4 out of 5
32 Star Island Rd Montauk NY
$299 nightly
The price is $341 total per night from May 14 to May 15
$341 total
May 14 - May 15
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 ...
Unhinged wacko

Reviewed on May 6, 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
$593 nightly
The price is $677 total per night from May 17 to May 18
$677 total
May 17 - May 18
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 ...
Stellar staff who made us feel most welcome. Loved the diversity of the team. Unforgettable scenery and experiences. We will definitely come back!

Reviewed on May 11, 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
$358 nightly
The price is $409 total per night from May 27 to May 28
$409 total
May 27 - May 28
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 ...
They charged us for parking in front of our room. Unbelievable. We stayed there in April, off season, the motel was empty.

Reviewed on May 11, 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 refundable
$87 nightly
The price is $100 total per night from May 25 to May 26
$100 total
May 25 - May 26
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 ...
The problem is that you can hear everything in all of the rooms above and to the right and left of you. I had a room on the first floor. I could hear every door shut, every step taken above me, and and most every conversation going on around me. It's a cute little place not far from the town center ...

Reviewed on May 11, 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 $100. 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 4,787 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

Ocean Surf Resort

Ocean Surf Resort

1 out of 5
Posted 9 hours ago
Travelocity Verified Review
"We were very disappointed after we got home and saw our card was charged about $40. When I called I was told it was a hotel tax. When I book through Expedia I assume it’s a One stop shop to book trips and pay what I owe at time of booking, not have a surprise charge for something made up. You work hard to try and afford a trip and then get charged more money. Expedia contacted them to try and remedy and they said to agent, it was for WiFi, CHAIRS, TOWELS! What does that even mean?! We were there one night in May, no chairs were used or towels, we didn’t even use the shower! Needless to say, that was our last time at this place. BEWARE OF EXTRA weird charges."
A verified traveler stayed at Ocean Surf Resort
Ocean Surf Resort

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