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Hotels with Swimming Pool in Shelter Island, New York

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Top Shelter Island Hotels with Swimming Pool

Frequently asked questions

What are some accommodations with pools in Shelter Island?
Marram: Hotel, 6-minute walk from The Hamptons Beaches. Features free self parking, a seasonal outdoor pool, and sun loungers. Quality Inn Old Saybrook - Westbrook: Offers buffet, an indoor pool, and free self parking. Montauk Blue Hotel: Hotel, 1-minute walk from The Hamptons Beaches. Provides sun loungers, an indoor pool, and complimentary wireless internet access. Montauk Yacht Club: Hotel, 5-minute walk from The Hamptons Beaches. Features 2 outdoor pools, a children's 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.
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, Shelter Island Whale's Tail, and Wades Beach 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.