Shelter Island Packages (Flight + Hotel)
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Where to stay in Shelter Island
Silver Beach
While Silver Beach may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Sunset Beach and Crescent Beach.
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
Staying at Gurney's after their many renovations was surprising !! The rooms don't look outdated anymore including the Spa / Pool area - for the price you're paying per night, I appreciated the face lift. Oceanviews from any angle of this hotel site will always be incredible !
Reviewed on 12 Jan 2026
Pier Blue Inn Old Saybrook - Essex
muy limpias
Reviewed on 8 Jan 2026
Montauk Blue Hotel
Great view of sunrise and sunset
Reviewed on 19 Jan 2026
Popular places to visit
Shell Beach
Why not spend a care-free afternoon at Shell Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums.
Wades Beach
Why not spend a care-free afternoon at Wades Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums.
What to do in Shelter Island
