Find Shelter Island Hotels with Swimming Pool

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Top Hotels with Swimming Pools in Shelter Island

Frequently asked questions

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 accommodation that has an outdoor pool if you’ll be visiting Shelter Island in the hottest months of August, July or September, when the average temp is 21°C. Accommodation 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 3°C.