Book Hotels in Shelter Island, NY

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Top Shelter Island hotels

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

Opens in a new windowMontauk Blue Hotel
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
$148 nightly
The price is $169 total per night from Feb 12 to Feb 13
$169 total
Feb 12 - Feb 13
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 ...
Beautiful room and beautiful setting. Love the fireplace!

Reviewed on Feb 9, 2026

Opens in a new windowMontauk Manor
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
$113 nightly
The price is $129 total per night from Feb 16 to Feb 17
$129 total
Feb 16 - Feb 17
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 ...
Clean cozy always enjoy our stay

Reviewed on Feb 7, 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 12 to Feb 13
$281 total
Feb 12 - Feb 13
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 room and staff

Reviewed on Jan 14, 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
$163 nightly
The price is $186 total per night from Feb 17 to Feb 18
$186 total
Feb 17 - Feb 18
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 ...
Lovely hotel with great location in town. Great free breakfast and wonderful staff. We will return!

Reviewed on Feb 6, 2026

Opens in a new windowThe Harbor Front Inn
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
$178 nightly
The price is $203 total per night from Feb 23 to Feb 24
$203 total
Feb 23 - Feb 24
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 our fourth trip back to the Soundview Inn, and we are big fans! The atmosphere is simple, modern, with a laid-back vibe. The rooms are well appointed and are finished with an indoor/outdoor use in mind. The room can be chilly in the winter, but it’s easy to get cozy. The included breakfast ...

Reviewed on Jan 10, 2026

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
$368 nightly
The price is $420 total per night from Feb 22 to Feb 23
$420 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 ...
Room was spotless, staff were great and the resort is top notch!!

Reviewed on Feb 2, 2026

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
$79 nightly
The price is $91 total per night from Feb 12 to Feb 13
$91 total
Feb 12 - Feb 13
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 ...
Room was clean and warm and the staff was very friendly

Reviewed on Feb 1, 2026

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
$101 nightly
The price is $116 total per night from Feb 17 to Feb 18
$116 total
Feb 17 - Feb 18
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. ...
Hotel was very clean, staff was wonderful and the pool was so relaxing. It was a quick visit but definitely would stay again if I was in that area.

Reviewed on Jan 28, 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 $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 4,688 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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