Shelter Island Holidays
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Top Flight + Hotel Deals in Shelter Island
Night Hotel Broadway
Reviewed on 2 Nov 2025
1 Hotel Central Park
Reviewed on 3 Nov 2025
Where to stay in Shelter Island
Coecles Harbor
While Coecles Harbor isn't home to many top sights, Shelter Island Whale's Tail and Gardiner's Bay Country Club are some notable places to visit nearby.
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
Unbelievable stay! Staff was very accommodating. Beautiful views. Redone very nicely
Reviewed on 26 Oct 2025
Pier Blue Inn Old Saybrook - Essex
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
Montauk Blue Hotel
Great view of the ocean with nice balcony.
Reviewed on 26 Oct 2025
What to do in Shelter Island
Long Island Wine and Food Day Trip with Sommelier host from NYC
