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Find Hotels with a Pool in Shelter Island, NY

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Check availability on Shelter Island Hotels with a Pool

Tonight
Aug 2 - Aug 3
Tomorrow
Aug 3 - Aug 4
Next weekend
Aug 8 - Aug 10
In two weeks
Aug 15 - Aug 17

Top Shelter Island Hotels with a Pool

Clinton Motel
Relax by the pool surrounded by lush greenery and comfortable lounge chairs.

Clinton Motel

2.5 star property
8.6 out of 10, Excellent, (261)
"For the money this reservation was a real win Clean lovely pool area convenient to everything"
The price is ₩109,768
₩126,233 total
includes taxes & fees
Aug 31 - Sep 1
Clinton Motel
Quality Inn Old Saybrook - Westbrook
Relax by the oval-shaped pool surrounded by lounge chairs and a high ceiling with a grid-like pattern.

Quality Inn Old Saybrook - Westbrook

2.5 star property
7.6 out of 10, Good, (1001)
"Great location and pool, close to a wonderful restaurant "
The price is ₩153,536
₩176,566 total
includes taxes & fees
Aug 10 - Aug 11
Quality Inn Old Saybrook - Westbrook
Econo Lodge Inn & Suites Old Saybrook Westbrook
Surrounded by lush greenery, a serene pond with a central fountain offers a peaceful escape.

Econo Lodge Inn & Suites Old Saybrook Westbrook

2.0 star property
7.2 out of 10, Good, (440)
"Room was very comfortable. I would definitely use again."
The price is ₩111,894
₩128,678 total
includes taxes & fees
Aug 10 - Aug 11
Econo Lodge Inn & Suites Old Saybrook Westbrook
Greenporter Hotel
Relax by the fire pit surrounded by comfortable seating and a serene pool view.

Greenporter Hotel

2.0 star property
9.2 out of 10, Wonderful, (154)
"Great place "
The price is ₩211,408
₩241,533 total
includes taxes & fees
Sep 2 - Sep 3
Greenporter Hotel
Ocean Vista Resort
Swimmers can enjoy the large indoor pool with a clear blue water surface, surrounded by a tiled floor and marked depth indicators.

Ocean Vista Resort

2.5 star property
9.0 out of 10, Wonderful, (183)
"It waa great for traveling with kids. Close to the beach and my kids loved the indoor pool!"
The price is ₩270,460
₩309,018 total
includes taxes & fees
Sep 1 - Sep 2
Ocean Vista Resort
Breakers Montauk
Relax by the oceanfront pool surrounded by lush greenery and comfortable lounge chairs.

Breakers Montauk

3.0 star property
8.4 out of 10, Very Good, (155)
"Wonderful, well kept place. Convenient to the ocean. The pool is nice and it was great having a restaurant on site!"
The price is ₩264,138
₩347,062 total
includes taxes & fees
Sep 1 - Sep 2
Breakers Montauk
Harborside Motel
Enjoy waterfront views and access to a marina from this coastal property, featuring a swimming pool and lush surroundings.

Harborside Motel

2.5 star property
8.8 out of 10, Excellent, (110)
"I booked last minute and the owner could not have been nicer. She was lovely and the room was immaculate. "
The price is ₩270,947
₩309,560 total
includes taxes & fees
Sep 1 - Sep 2
Harborside Motel
Hampton's Vacation Inn
Relax by the pool with lounge chairs and a shaded seating area nearby.

Hampton's Vacation Inn

2.5 star property
9.0 out of 10, Wonderful, (293)
"Great place highly recommended. Quiet and cozy atmosphere. Pool, tennis court, volleyball court and onsite parking made the stay that much better. Amazing staff and super professional. "
The price is ₩281,368
₩321,468 total
includes taxes & fees
Aug 3 - Aug 4
Hampton's Vacation Inn
Budget Host East End Hotel in Riverhead
Relax by the rectangular pool surrounded by a tiled deck and lounge chairs.

Budget Host East End Hotel in Riverhead

2.0 star property
6.6 out of 10, (729)
"Nice place"
The price is ₩143,810
₩164,302 total
includes taxes & fees
Aug 10 - Aug 11
Budget Host East End Hotel in Riverhead
Ocean Resort Inn
Relax by the pool surrounded by lush greenery and comfortable lounge chairs.

Ocean Resort Inn

2.0 star property
9.6 out of 10, Exceptional, (434)
"We will return here its a great Location "
The price is ₩318,189
₩386,175 total
includes taxes & fees
Sep 1 - Sep 2
Ocean Resort Inn
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.

Top Shelter Island Hotel Reviews

Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

10/10 Excellent
"Absolutely loved our stay. I can’t wait to go back next year! "
Tracey 3-night trip
Posted 2 days ago
Beachcomber Resort at Montauk

Frequently asked questions

What are some accommodations with pools in Shelter Island?
Marram: Hotel, 6-minute walk from The Hamptons Beaches. Features free self parking, a seasonal outdoor pool, and sun loungers. Quality Inn Old Saybrook - Westbrook: Offers buffet, an indoor pool, and free self parking. Montauk Yacht Club: Hotel, 5-minute walk from The Hamptons Beaches. Provides 2 outdoor pools, a children's pool, and a private beach. Pier Blue Inn Old Saybrook - Essex: Resort, 13-minute walk from The Hamptons Beaches. Offers a seasonal outdoor pool, an indoor pool, and a private beach. 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.
What is there to see and do in Shelter Island?
Surround yourself with nature at Sunset Beach and Crescent Beach. Discover sights such as Shelter Island Whale's Tail, Gardiner's Bay Country Club, and Shelter Island Historical Society during your stay.
When is the best time to book a hotel with a pool in Shelter Island?
You may want to think about an accommodation that has an outdoor pool if you will be visiting Shelter Island in the hottest months of August, July, or September when the average temp is 70°F. Lodging offering an indoor pool may be what you want if you come to town during the coldest months of January, February, or March when the average temperature is 38°F.