Book Hotels in Shelter Island, NY

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Top Shelter Island hotels

Ocean Resort Inn

Ocean Resort Inn

2 out of 5
95 S Emerson Ave Montauk NY
$155 nightly
The price is $177 total per night from Sep 27 to Sep 28
$177 total
Sep 27 - Sep 28
Total with taxes and fees
A seasonal outdoor pool, free self parking, and concierge services are featured at this motel. WiFi in public areas is free. A garden and a picnic area are also ...
"Closest to beach and town"

Reviewed on Sep 21, 2026

Opens in a new windowOcean Resort Inn
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
$218 nightly
The price is $251 total per night from Oct 7 to Oct 8
$251 total
Oct 7 - Oct 8
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 ...
"The staff at the Bistro Bar weren't very good. Also the drinks sub par. I ordered a gin and tonic, they served me soda water twice."

Reviewed on Sep 23, 2026

Opens in a new windowWater's Edge Resort & Spa
Ocean Surf Resort

Ocean Surf Resort

2 out of 5
84 South Emerson Avenue Montauk NY
$130 nightly
The price is $148 total per night from Oct 19 to Oct 20
$148 total
Oct 19 - Oct 20
Total with taxes and fees
A seasonal outdoor pool, self parking, and concierge services are featured at this motel. WiFi in public areas is free. A terrace, a picnic area, and luggage ...
"it was a lovely stay at the Ocean surf resort. We went in September and the weather was spectacular. We really enjoyed watching the sea life from the deck. We saw so many whales, dolphins and seals too. It was quiet enough to get a night's sleep and the mattress was pretty good too. My only issue ..."

Reviewed on Sep 23, 2026

Opens in a new windowOcean Surf Resort
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39 Southampton NY
$119 nightly
The price is $136 total per night from Oct 25 to Oct 26
$136 total
Oct 25 - Oct 26
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 ...
"I expected at least a 3 star hotel type for this place. however it was pretty disappointed for my family. it is just a motel Inn. nothing more. staff was friendly. but they get off very early where we cannot reach anyone after certain time. no staff u can find near the Inn when it gets dark. so I ..."

Reviewed on Sep 23, 2026

Opens in a new windowThe Atlantic Hotel
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
$91 nightly
The price is $104 total per night from Sep 30 to Oct 1
$104 total
Sep 30 - Oct 1
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 ...
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
$450 nightly
The price is $514 total per night from Sep 29 to Sep 30
$514 total
Sep 29 - Sep 30
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 ...
Opens in a new windowGurney's Montauk Resort & Seawater Spa
Offshore Montauk

Offshore Montauk

4 out of 5
71 S Emerson Ave Montauk NY
$222 nightly
The price is $253 total per night from Sep 29 to Sep 30
$253 total
Sep 29 - Sep 30
Total with taxes and fees
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
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
$270 nightly
The price is $308 total per night from Oct 18 to Oct 19
$308 total
Oct 18 - Oct 19
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 ...
Opens in a new windowSound View Greenport
Montauk Blue Hotel

Montauk Blue Hotel

2 out of 5
108 South Emerson Avenue Montauk NY
$165 nightly
The price is $188 total per night from Oct 20 to Oct 21
$188 total
Oct 20 - Oct 21
Total with taxes and fees
This hotel features an indoor pool and a hot tub. WiFi in public areas is free. A terrace, a picnic area, and luggage storage are also on offer.
Opens in a new windowMontauk Blue 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 $104. 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 4,644 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

Zey Hotel

Zey Hotel

5 out of 5
Posted 2 hours ago
Travelocity Verified Review
"Lovely hotel, great location and lovely courtyard!"
A verified traveler stayed at Zey Hotel
Zey Hotel

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