A pebbled beach with a sunset and a distant bridge.

Hotels with Swimming Pools in Shelter Island Heights

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Check availability on Shelter Island Heights Hotels with Swimming Pools

Our top choices for Shelter Island Heights hotels with a pool

Seasonal outdoor pool, pool umbrellas, pool loungers

The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (91 reviews)
  • cleanliness
    Splash into coastal luxury at this beachfront hotel with a seasonal pool, spa, and private beach access.
The price is S$1,221
includes taxes & fees
3 Aug - 4 Aug
The Pridwin Hotel
Beach nearby

West Neck Guesthouse

West Neck Guesthouse
3.5 star property
Shelter Island Heights
8.2 out of 10, Very good, (42 reviews)
  • cleanliness
    Charming B&B features seasonal outdoor pool and free bicycle rentals for guests.
The price is S$463
includes taxes & fees
15 Jul - 16 Jul
West Neck Guesthouse
Property amenity

Shelter Island House

Shelter Island House
3.5 star property
Shelter Island Heights
8.4 out of 10, Very good, (59 reviews)
  • cleanliness
    Relaxing seasonal pool oasis beckons at this Shelter Island retreat, where a poolside bar enhances sun-drenched afternoons.
The price is S$467
includes taxes & fees
30 Jul - 31 Jul
Shelter Island House
Seasonal outdoor pool

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (321 reviews)
  • cleanliness
    Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
The price is S$132
includes taxes & fees
13 Jul - 14 Jul
Clinton Motel
Lobby sitting area

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,001 reviews)
  • cleanliness
    Plunge into pool paradise at this welcoming hotel with sun loungers and a relaxing indoor retreat.
The price is S$176
includes taxes & fees
2 Aug - 3 Aug
Quality Inn Old Saybrook - Westbrook
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

Best Western Niantic - New London/Mystic Area

Best Western Niantic - New London/Mystic Area
2.5 star property
Niantic
9.0 out of 10, Wonderful, (557 reviews)
  • cleanliness
    Scenic oasis awaits at Niantic hotel featuring seasonal pool, sun loungers, and umbrella-shaded areas.
The price is S$210
includes taxes & fees
21 Jul - 22 Jul
Best Western Niantic - New London/Mystic Area
Indoor pool, a heated pool

Sleep Inn & Suites Niantic North

Sleep Inn & Suites Niantic North
2.5 star property
Niantic
8.4 out of 10, Very good, (1,007 reviews)
  • cleanliness
    Refreshing indoor pool retreat just steps from the beach makes a splash for aquatic adventures.
The price is S$163
includes taxes & fees
5 Aug - 6 Aug
Sleep Inn & Suites Niantic North
Exterior

Water's Edge Resort & Spa

Water's Edge Resort & Spa
3.5 star property
Westbrook Center
8.8 out of 10, Excellent, (1,002 reviews)
  • cleanliness
    Pristine waters await at this coastal retreat with private beach access and year-round pools.
The price is S$541
includes taxes & fees
22 Jul - 23 Jul
Water's Edge Resort & Spa
Reception

The Penny Lane

The Penny Lane
3.0 star property
Hampton Bays
9.0 out of 10, Wonderful, (86 reviews)
  • cleanliness
    Seasonal poolside relaxation awaits at this oceanfront hotel with sun loungers, umbrellas, and gardens.
The price is S$361
includes taxes & fees
10 Aug - 11 Aug
The Penny Lane
View from property

Breakers Montauk

Breakers Montauk
3.0 star property
Montauk
8.6 out of 10, Excellent, (208 reviews)
  • cleanliness
    Seaside poolside escape with sun loungers and umbrellas creates a summer sanctuary.
The price is S$519
includes taxes & fees
29 Jul - 30 Jul
Breakers Montauk
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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Choose what matters most at hotels with a pool in Shelter Island Heights

Breakfast included
4 stars

Top Shelter Island Heights Hotel Reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

8/10 Good
"Our room was lovely however it was on the second floor of the building with no elevator. There were 14 steep steps that had to be climbed. My husband (84) had trouble doing this. We were not notified of the steps when we made our reservations. When I asked for a different room, I was told they were all filled. Restaurant: Food good but expensive and took a long time to arrive. More stairs to get to the dining room. To use the elevator one needed to pass through the kitchen. Beach: Wall to wall deck chairs. One would have more room at a public beach."
Marjorie 2-night trip
Posted 20 hours ago
Water's Edge Resort & Spa

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. Gurney's Montauk Resort & Seawater Spa: Resort, 13-minute walk from The Hamptons Beaches. Offers a seasonal outdoor pool, an indoor pool and a private beach. Pier Blue Inn Old Saybrook - Essex: Hotel, 1-minute walk from The Hamptons Beaches. Features a sauna, a seasonal outdoor pool and free self parking. Offshore Montauk: Aparthotel, 14-minute walk from The Hamptons Beaches. Offers a seasonal outdoor pool, an indoor pool and 3 outdoor tennis courts. Montauk Manor: Features 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?
Explore places such as The Hamptons Beaches while you're in the area. Enjoy a stroll along the shore at Sunset Beach and Crescent Beach. 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.

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