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Find Hotels with a Pool in Shelter Island, NY

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

Frequently asked questions

What are some accommodations with pools in Shelter Island?
Quality Inn Old Saybrook - Westbrook: Features buffet, an indoor pool, and free self parking. Gurney’s Montauk Resort & Seawater Spa: Offers a seasonal outdoor pool, an indoor pool, and a private beach. Montauk Manor: Provides sun loungers, an outdoor pool, and kitchens. Hyatt Place Long Island East End: Features a seasonal outdoor pool, an indoor pool, and 3 outdoor tennis courts. Saybrook Point Resort & Marina: Offers an indoor pool, an outdoor pool, and 2 bars.
What is there to see and do in Shelter Island?
Surround yourself with nature at Sunset Beach and Crescent Beach. Discover sights such as Shelter Island Historical Society, Mashomack Preserve, and Gardiner’s Bay Country Club 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.