Shelter Island Trip

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Photo by Brian V. Rowe
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Top Shelter Island Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza New York Times Square
Hotel Riu Plaza Manhattan Times Square
INNSiDE by Meliá New York Nomad
Eurostars Wall Street
Millennium Premier New York Times Square

Where to stay in Shelter Island

Find the best Shelter Island areas and neighborhoods for the activities you enjoy most. Learn more about Shelter Island

Shelter Island Beach Holiday

There's nothing like a Shelter Island holiday to give you a little extra bounce in your step. The sound of rolling surf and the smell of clean ocean air are sure to refresh your mind, body and soul. To be close to the town centre on your trip to Shelter Island, find a hotel around Wades Beach (2 kilometres away). If you're planning to stay for a bit, look into our Shelter Island packages. Not only can you save some cash, you'll also have other amazing beaches near you to explore, like Shell Beach and Menhadden Lane Beach.

Top hotels in Shelter Island

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 ₹22,184 per night from 2 Dec to 3 Dec
₹22,184
₹30,277 total
2 Dec - 3 Dec
includes taxes & fees
8.2/10 Very Good! (688 reviews)
Amazing experience.

Reviewed on 10 Nov 2025

Gurney'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
7.8/10 Good! (1,002 reviews)
The room was very clean with soft towels. The sheets were clean but a bit rougher than I'm used to (I like silky sheets, not rough cotton) but the bed was comfortable and warm. The staff is very friendly too. A nice "basic" room that took care of our needs, didn't gross me out with smell or dirt ...

Reviewed on 3 Nov 2025

Pier Blue Inn Old Saybrook - Essex
Montauk Blue Hotel

Montauk Blue Hotel

2 out of 5
108 South Emerson Avenue Montauk NY
9/10 Wonderful! (181 reviews)
Location - beautiful view

Reviewed on 10 Nov 2025

Montauk Blue Hotel
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.

Popular places to visit

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.