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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
2 Oct - 3 Oct
Tomorrow
3 Oct - 4 Oct
This weekend
3 Oct - 5 Oct
Next weekend
10 Oct - 12 Oct

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, (79)
"Shelter Island is definitely a gem"
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!"
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

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent
"wonderful place only criticism is how far away rooms are from lobby and the rest of the facilities"
Darryl 3-night trip
Posted 3 days ago
Gurney's Montauk Resort & Seawater Spa

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 10 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: 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 sunloungers, 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 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.