A wooden gazebo by a pond with a large tree trunk nearby.

Find Hotels with a Pool in Shelter Island, NY

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Shelter Island Hotels with a Pool

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22

Choose what matters most at hotels with a pool in Shelter Island

Breakfast included
4 stars

Top Shelter Island Hotel Reviews

Ocean Vista Resort

Ocean Vista Resort

10/10 Excellent
"We love this place a lot, very beautiful beach and nice people"
Thanh 2-night trip
Posted 12 hours ago
Ocean Vista Resort

Frequently asked questions

What are some accommodations with pools in Shelter Island?
Pier Blue Inn Old Saybrook - Essex: Resort, 13-minute walk from The Hamptons Beaches. Offers a seasonal outdoor pool, an indoor pool, and a private beach. Gurney's Montauk Resort & Seawater Spa: Hotel, 1-minute walk from The Hamptons Beaches. Provides a sauna, a seasonal outdoor pool, and free self parking. Offshore Montauk: Features a seasonal outdoor pool, an indoor pool, and a private beach. Water's Edge Resort & Spa: Offers a private beach, a seasonal outdoor pool, and 2 bars. Sound View Greenport: Hotel, 1-minute walk from The Hamptons Beaches. Features sun loungers, an indoor pool, and complimentary wireless internet access.
What is there to see and do in Shelter Island?
Surround yourself with nature at Mashomack Preserve and Sunset Beach. Discover sights such as Shelter Island Historical Society, Wades Beach, and Crescent 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.

Explore a world of travel with Expedia