Book Hotels in Shelter Island, NY

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Top Shelter Island hotels

Montauk Yacht Club

Montauk Yacht Club

4.5 out of 5
32 Star Island Rd Montauk NY
The price is $901 total per night from Jul 30 to Jul 31
$901 total
per night
Jul 30 - Jul 31
This luxury hotel features a private beach, a marina, and 2 restaurants. Traveling on business? Take advantage of the 5 conference rooms, along with free WiFi ...
"It was not user-friendly for handicap people my mother used a Rollator there were stairs everywhere, uneven blocks, etc. you always had to go take steps to your room up or down The serving staff was excellent But be careful of additional charges as I had to really review my folio and was refunded ..."

Reviewed on Jul 22, 2026

Opens in a new windowMontauk Yacht Club
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is $426 total per night from Aug 12 to Aug 13
$426 total
per night
Aug 12 - Aug 13
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 ...
"Room has a porch but it wasn’t private, people from next room had to walk through our porch to get to stairs to the beach. Room has no dresser or shelves for clothing, no shelf in bathroom for toiletries or anything else. One glass in room for beverages, no other glasses in room or bathroom. Area ..."

Reviewed on Jul 27, 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
The price is $76 total per night from Jul 28 to Jul 29
$76 total
per night
Jul 28 - Jul 29
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 ok. Air conditioning worked but noisy."

Reviewed on Jul 26, 2026

Opens in a new windowPier Blue Inn Old Saybrook - Essex
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
The price is $1,219 total per night from Jul 29 to Jul 30
$1,219 total
per night
Jul 29 - Jul 30
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 ...
Opens in a new windowGurney's Montauk Resort & Seawater Spa
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39 Southampton NY
The price is $281 total per night from Aug 10 to Aug 11
$281 total
per night
Aug 10 - Aug 11
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 ...
Opens in a new windowThe Atlantic Hotel
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
The price is $350 total per night from Jul 29 to Jul 30
$350 total
per night
Jul 29 - Jul 30
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 ...
Opens in a new windowWater's Edge Resort & Spa
Marram

Marram

4 out of 5
21 Oceanview Terrace Montauk NY
The price is $996 total per night from Aug 9 to Aug 10
$996 total
per night
Aug 9 - Aug 10
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 ...
Opens in a new windowMarram
Offshore Montauk

Offshore Montauk

4 out of 5
71 S Emerson Ave Montauk NY
The price is $622 total per night from Jul 29 to Jul 30
$622 total
per night
Jul 29 - Jul 30
This hotel features a gym and a seasonal outdoor pool. Enjoy the sauna and perks like free self parking and free WiFi. Express check-out and luggage storage ...
Opens in a new windowOffshore Montauk
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
The price is $549 total per night from Aug 10 to Aug 11
$549 total
per night
Aug 10 - Aug 11
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 ...
Opens in a new windowMontauk Manor
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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 $76. 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 4,734 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

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

4 out of 5
Posted 23 hours ago
Travelocity Verified Review
"Room was ok. Air conditioning worked but noisy. "
A verified traveler stayed at Pier Blue Inn Old Saybrook - Essex
Pier Blue Inn Old Saybrook - Essex

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