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Find Hotels with a Pool in Shelter Island, NY

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Check availability on Shelter Island Hotels with a Pool

Compare Shelter Island Hotels with a Pool room rates, reviews, and availability. Most hotels are fully refundable.

Frequently asked questions

What are some accommodations with pools in Shelter Island?
Water’s Edge Resort & Spa: Features a seasonal outdoor pool, an indoor pool, and a private beach. Gurney’s Montauk Resort & Seawater Spa: Resort, 13-minute walk from The Hamptons Beaches. Offers a seasonal outdoor pool, an indoor pool, and a private beach. Montauk Manor: Aparthotel, 14-minute walk from The Hamptons Beaches. Provides a seasonal outdoor pool, an indoor pool, and 3 outdoor tennis courts. Pier Blue Inn Old Saybrook - Essex: Offers an indoor pool, an outdoor pool, and 2 bars. Hyatt Place Long Island East End: Hotel, 5-minute walk from The Hamptons Beaches. Features 2 outdoor pools, a children’s pool, and a private beach.
What is there to see and do in Shelter Island?
Surround yourself with nature at Sunset Beach and Crescent Beach. Discover sights such as Gardiner’s Bay Country Club, Shelter Island Historical Society, and Havens House during your stay.
When is the best time to book a hotel with a pool in Shelter Island?
You may want to think about an accommodation that has an outdoor pool if you will be visiting Shelter Island in the hottest months of August, July, or September when the average temp is 70°F. Lodging offering an indoor pool may be what you want if you come to town during the coldest months of January, February, or March when the average temperature is 38°F.