Book Hotels in Shelter Island, NY

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Top Shelter Island hotels

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
2 Bridge St, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
$277 nightly
The price is $318 total per night from Nov 19 to Nov 20
$318 total
Nov 19 - Nov 20
Total with taxes and fees
A full-service spa, a marina, and 2 outdoor pools are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public ...
"Location"

Reviewed on Oct 14, 2025

Opens in a new windowSaybrook Point Resort & Marina
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
$148 nightly
The price is $169 total per night from Oct 22 to Oct 23
$169 total
Oct 22 - Oct 23
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 ...
"It was very spacious!"

Reviewed on Oct 17, 2025

Opens in a new windowThe Bentley Hotel Southampton
Montauk Blue Hotel

Montauk Blue Hotel

2 out of 5
108 South Emerson Avenue, Montauk, NY
$119 nightly
The price is $136 total per night from Nov 9 to Nov 10
$136 total
Nov 9 - Nov 10
Total with taxes and fees
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.
"Didn’t get to stay the night had a family emergency had to leave an hour after I checked in. Hope to get credited for another stay in the future. Staff was very nice."

Reviewed on Oct 13, 2025

Opens in a new windowMontauk Blue Hotel
Marram

Marram

4 out of 5
21 Oceanview Terrace, Montauk, NY
$283 nightly
The price is $323 total per night from Oct 29 to Oct 30
$323 total
Oct 29 - Oct 30
Total with taxes and fees
A seasonal outdoor pool, free self parking, and wedding services are featured at this hotel. WiFi in public areas is free. A terrace, a garden, and luggage storage ...
"We came during terrible weather and couldn’t enjoy the amenities but the view and overall property is beautiful. Johnny at the front desk was very friendly and helpful."

Reviewed on Oct 13, 2025

Opens in a new windowMarram
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48, Greenport, NY
$266 nightly
The price is $304 total per night from Oct 26 to Oct 27
$304 total
Oct 26 - Oct 27
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 ...
"There was some deck furniture that needed repair. No microwave?? Why?"

Reviewed on Oct 9, 2025

Opens in a new windowSound View Greenport
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway, Montauk, NY
$330 nightly
The price is $377 total per night from Nov 4 to Nov 5
$377 total
Nov 4 - Nov 5
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 ...
"We had a lovely one night stay. Everyone was very friendly. Having my dogs there was a treat. The spa was great and relaxing. GIGI’s restaurant is a must. The only complaint I have is that the bedclothes need to be updated. They were torn/frayed in multiple places. Other than that it was a great ..."

Reviewed on Oct 11, 2025

Opens in a new windowGurney's Montauk Resort & Seawater Spa
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
$80 nightly
The price is $92 total per night from Oct 23 to Oct 24
$92 total
Oct 23 - Oct 24
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 staff were super nice. The room was clean. For the price point it was a good value."

Reviewed on Oct 17, 2025

Opens in a new windowPier Blue Inn Old Saybrook - Essex
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
$94 nightly
The price is $108 total per night from Nov 2 to Nov 3
$108 total
Nov 2 - Nov 3
Total with taxes and fees
This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. ...
"Our stay was just what we needed. Breakfast was full of choices and and plenty to eat and drink. A perfect stop in a lovely town."

Reviewed on Oct 12, 2025

Opens in a new windowQuality Inn Old Saybrook - Westbrook
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39, Southampton, NY
$138 nightly
The price is $158 total per night from Nov 3 to Nov 4
$158 total
Nov 3 - Nov 4
Total with taxes and fees
This hotel's 2 outdoor tennis courts and outdoor pool are among the featured amenities. Guests will appreciate free perks like free self parking and WiFi in ...
"Great stay overall. Only suggestion would be to put a light on the side of the building."

Reviewed on Oct 13, 2025

Opens in a new windowThe Atlantic Hotel
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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 $92. 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 4,723 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

Offshore Montauk

Offshore Montauk

5 out of 5
Posted 3 days ago
Travelocity Verified Review
"Beautifully renovated , super clean property. High quality sheets, towels, very comfortable bed. We enjoyed easy access to the beach and short distance to many dining options. Had wonderful stay and can't wait to come back."
A verified traveler stayed at Offshore Montauk
Offshore Montauk

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