Photo by Erisa Dilo

Find Hotels with a Pool in Shelter Island Heights, NY

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Pick from 3 Shelter Island Heights Hotels with a Pool and compare room rates, reviews, and availability. Most hotels are fully refundable.

The Pridwin Hotel
Pool

The Pridwin Hotel

4.0 star property
9.6 out of 10, Exceptional, (57)
"Fantastic property. Rooms are beautifully appointed, decor is super chic and comfortable. Gorgeous views and amenities. Absolutely enjoyed our second stay at The Pridwin!"
The Pridwin Hotel
Shelter Island House
Outdoor pool

Shelter Island House

3.5 star property
8.4 out of 10, Very Good, (56)
"Everything was excellent. However, it would have been nice if there had been something offered for breakfast."
Shelter Island House
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Frequently asked questions

What's it like visiting Shelter Island Heights?
If lounging by a pool is your idea of a great vacation, you may want to check out Shelter Island Heights, which has 6 places to stay with pools. While you’re visiting, you can explore sights such as Sunset Beach and Crescent Beach, and then kick back and relax poolside at one of the accommodations in Shelter Island Heights that guests like for their pools.
What are some accommodations with pools in Shelter Island Heights?
The Rams Head Inn: Offers buffet, an indoor pool, and free self parking. Quality Inn Old Saybrook - Westbrook: Features a seasonal outdoor pool, an indoor pool, and a private beach. Pier Blue Inn Old Saybrook - Essex: Offers sun loungers, an outdoor pool, and kitchens. Gurney’s Montauk Resort & Seawater Spa: Features 2 outdoor pools, an indoor pool, and a full-service spa. Saybrook Point Resort & Marina: Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access.
How many pool hotels will I find in Shelter Island Heights?
Expedia has 6 hotels in Shelter Island Heights for your poolside break.
What is there to see and do in Shelter Island Heights?
Spend some time experiencing the great outdoors at Sunset Beach and Crescent Beach. Discover sights such as Shelter Island Country Club, Sylvester Manor, and Menhadden Lane Beach during your stay. Take in the natural beauty of Shelter Island Heights with the island views and beaches.
When is the best time to book a hotel with a pool in Shelter Island Heights?
You may want to think about a place to stay with an outdoor swimming pool if you will be visiting Shelter Island Heights in the warmest months of August, July, or September when the average temp is 70°F. Lodging offering an indoor pool may be the way to go if you are visiting during the coldest months of January, February, or March when the average temp is 38°F.