Photo by tom owens

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. Sound View Greenport: Offers a private beach, a seasonal outdoor pool, and 2 bars. Gurney’s Montauk Resort & Seawater Spa: Provides a seasonal outdoor pool, an indoor pool, and a private beach. Pier Blue Inn Old Saybrook - Essex: Offers 2 outdoor pools, a children’s pool, and a private beach. Montauk Yacht Club: Features 2 outdoor pools, an indoor pool, and a full-service spa.
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 Shell 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.