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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
Oct 30 - Oct 31
Tomorrow
Oct 31 - Nov 1
This weekend
Oct 31 - Nov 2
Next weekend
Nov 7 - Nov 9

Top Shelter Island Hotels with a Pool

Outdoor pool, a heated pool
Work and Play Special! Extended Stay Discount
Work and Play Special! Extended Stay Discount
10.0 out of 10, Exceptional, (52)
"Really great property, had a relaxing lovely time!"
United States
Nava S.
The price is ￥109,562
￥202,541 total
includes taxes & fees
Nov 5 - Nov 6
Work and Play Special! Extended Stay Discount
Seasonal outdoor pool
Clinton Motel
Clinton Motel
2.5 star property
8.6 out of 10, Excellent, (289)
"Great staff and clean rooms"
United States
Tyler
The price is ￥11,907
￥13,693 total
includes taxes & fees
Nov 2 - Nov 3
Clinton Motel
Indoor pool, open 10:00 AM to 6:00 PM, sun loungers
Montauk Blue Hotel
Montauk Blue Hotel
2.0 star property
9.2 out of 10, Wonderful, (174)
"The beach view is spectacular the surrounding area has everything you need for a each getaway"
United States
Jason
The price is ￥17,022
￥19,447 total
includes taxes & fees
Nov 9 - Nov 10
Montauk Blue Hotel
Seasonal outdoor pool, pool umbrellas, sun loungers
Kenny's Tipperary Inn
Kenny's Tipperary Inn
2.0 star property
8.4 out of 10, Very Good, (870)
"Really clean and nice location"
United States
Tiara
Kenny's Tipperary Inn
Exterior
Montauk Manor
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1258)
"Always excellent, even suring my eleventh stay."
United States
Daryl
The price is ￥23,008
￥29,268 total
includes taxes & fees
Nov 3 - Nov 4
Montauk Manor
Indoor pool, 2 outdoor pools
Montauk Yacht Club
Montauk Yacht Club
4.0 star property
8.6 out of 10, Excellent, (1005)
"Wonderful hotel and location "
United States
FIONA
Montauk Yacht Club
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Hamlet Inn
Hamlet Inn
2.0 star property
8.6 out of 10, Excellent, (433)
"A solid inexpensive stay in the Hamptons. Staff are very accommodating, they helped guide us when there was an upcoming storm. Room was comfortable and clean. "
United States
Michelle
The price is ￥16,297
￥21,064 total
includes taxes & fees
Nov 2 - Nov 3
Hamlet Inn
Outdoor pool, a heated pool
New and Modern Bridgehampton Accommodations
New and Modern Bridgehampton Accommodations
2.0 star property
9.6 out of 10, Exceptional, (15)
"Great home, as pictured, perfect place to stay!"
United States
Peter R.
The price is ￥26,706
￥65,980 total
includes taxes & fees
Nov 3 - Nov 4
New and Modern Bridgehampton Accommodations
Aerial view
Harborside Motel
Harborside Motel
2.5 star property
8.8 out of 10, Excellent, (122)
"I loved this family owned hotel, they really made sure to make you feel at home and gave great recommendations as locals!"
United States
Seth
The price is ￥23,662
￥27,034 total
includes taxes & fees
Oct 31 - Nov 1
Harborside Motel
BBQ/picnic area
Offshore Montauk
Offshore Montauk
2.0 star property
9.4 out of 10, Exceptional, (63)
"Great place "
United States
Kevin
The price is ￥17,547
￥37,488 total
includes taxes & fees
Nov 18 - Nov 19
Offshore 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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Top Shelter Island Hotel Reviews

The Atlantic Hotel

The Atlantic Hotel

10/10 Excellent
"Perfect "
Anthony 1-night trip
Posted 2 days ago
The Atlantic Hotel

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Frequently asked questions

What are some accommodations with pools in Shelter Island?
Gurney's Montauk Resort & Seawater Spa: 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: Hotel, 1-minute walk from The Hamptons Beaches. Features sun loungers, an indoor pool, and complimentary wireless internet access. Montauk Blue Hotel: Offers buffet, an indoor pool, and free self parking. Quality Inn Old Saybrook - Westbrook: Hotel, 6-minute walk from The Hamptons Beaches. Features free self parking, a seasonal outdoor pool, and sun loungers. Marram: Offers 2 outdoor pools, an indoor pool, and a full-service spa.
What is there to see and do in Shelter Island?
Surround yourself with nature at Sunset Beach and Crescent Beach. Discover sights such as Gardiner's Bay Country Club, Shelter Island Historical Society, and Havens House 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.