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Find Shelter Island Heights Hotels with Swimming Pool

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Top Hotels with Swimming Pools in Shelter Island Heights

The Pridwin Hotel
Seasonal outdoor pool, pool umbrellas, pool loungers
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
Terrace/patio
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 taking it easy by the pool is your idea of a great getaway, you may want to consider Shelter Island Heights, which offers 6 places to stay with pools. During your trip, you can explore sights such as Sunset Beach and Crescent Beach, and then relax poolside at one of the accommodation options in Shelter Island Heights that guests like for their pools.
What are some accommodation options with pools in Shelter Island Heights?
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 swimming pools, a children’s pool and a private beach. Montauk Yacht Club: Features 2 outdoor swimming pools, an indoor pool and a full-service spa.
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 that has an outdoor pool if you plan to visit Shelter Island Heights in the warmest months of August, July or September, when the average temp is 21°C. Accommodation offering an indoor pool may be the way to go if you come to town during the coldest months of January, February or March, when the average temp is 3°C.