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Hotels with Swimming Pool in Shelter Island Heights, New York

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Check availability on Shelter Island Heights Hotels with Swimming Pool

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Oct 2 - Oct 3
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Oct 3 - Oct 4
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Oct 3 - Oct 5
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Oct 10 - Oct 12

Top Shelter Island Heights Hotels with Swimming Pool

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

The Pridwin Hotel

4.0 star property
9.6 out of 10, Exceptional, (79)
"Shelter Island is definitely a gem"
The price is P16,172
P20,324 total
includes taxes & fees
Oct 19 - Oct 20
The Pridwin Hotel
Shelter Island House
Property amenity

Shelter Island House

3.5 star property
8.4 out of 10, Very Good, (56)
"We liked the areas for sitting outside, to sit with a coffee, talk and relax. It was convenient to have a fridge. A very different accommodation but typical for the island. We enjoyed our stay!"
The price is P11,713
P13,381 total
includes taxes & fees
Oct 5 - Oct 6
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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Top Shelter Island Heights Hotel Reviews

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

10/10 Excellent
"Liked having and using pool. didn't realize there would be a swimming lesson going on at same time. As this was a quick stop over on our way to Bar Harbor, it fit our needs. Since the room was on the street side it was a bit noisy even with fan running all the time. The room was clean and comfortable and we enjoyed the breakfast which was included. "
Michael 1-night trip
Posted 4 days ago
Quality Inn Old Saybrook - Westbrook

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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 10 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 Pridwin Hotel: Features a private beach, a seasonal outdoor pool, and a full-service spa. The Chequit: Resort, 13-minute walk from The Hamptons Beaches. Features a seasonal outdoor pool, an indoor pool, and a private beach. Pier Blue Inn Old Saybrook - Essex: Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Gurney's Montauk Resort & Seawater Spa: Hotel, 1-minute walk from The Hamptons Beaches. Features sun loungers, an indoor pool, and complimentary wireless internet access. Best Western Niantic - New London/Mystic Area: Offers a private beach, a seasonal outdoor pool, and 2 bars.
How many pool hotels will I find in Shelter Island Heights?
Expedia has 10 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.