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Hotels with Pool & Resorts in Shelter Island Heights

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Check availability on Shelter Island Heights Hotels with Pool

Tonight
19 Jul - 20 Jul
Tomorrow
20 Jul - 21 Jul
Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug

Best Shelter Island Heights Hotels with Pool

The Pridwin Hotel
Seasonal outdoor pool, pool umbrellas, pool loungers

The Pridwin Hotel

4.0 star property
9.6 out of 10, Exceptional, (65)
"The Pridwin is amazing for a shelter island getaway. The property is gorgeous and the access to the beach and
pool
, kayaking and pickleball courts leave nothing to be desired. The staff is wonderful and so accommodating. Don’t miss the summer Wednesday bbqs!"
Amanda
The Pridwin Hotel
Shelter Island House
Property amenity

Shelter Island House

3.5 star property
8.4 out of 10, Very good, (56)
"Very quiet, perfect for my short getaway, so peaceful! My second floor room was tucked away and LOVED the large cushy reading chair and ottoman. A/C super quiet! Bed was very comfortable (the pillows were like baby belugas so if you prefer a flatter pillow bring one?). Enjoyed the
pool
once the weather cooperated, nice and secluded. Suzanne (house manager) is so nice and very accommodating. I’d love to make a return visit! "
Christine
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.

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?
The Pridwin Hotel: Features a private beach, a seasonal outdoor pool and a full-service spa. The Chequit: Hotel, 6-minute walk from The Hamptons Beaches. Provides free self parking, a seasonal outdoor pool and sunloungers. Marram: Features buffet, an indoor pool and free self parking. Quality Inn Old Saybrook - Westbrook: Hotel, 1-minute walk from The Hamptons Beaches. Offers sunloungers, an indoor pool and complimentary wireless Internet access. Montauk Blue Hotel: Hotel, 5-minute walk from The Hamptons Beaches. Features 2 outdoor swimming pools, a children's pool and a private beach.
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.