Find Hotels with a Pool in Shelter Island, NY

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Check availability on Shelter Island Hotels with a Pool

Tonight
5 Dec - 6 Dec
Tomorrow
6 Dec - 7 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Shelter Island Hotels with a Pool

BBQ/picnic area
Offshore Montauk

Offshore Montauk

2.0 star property
Montauk
9.2 out of 10, Wonderful, (74)
"Excellent stay! Gorgeous views, very clean rooms, helpful staff and beautifully done. Will stay again!"
United States
Erica
The price is SAR 436
SAR 712 total
includes taxes & fees
18 Dec - 19 Dec
Offshore Montauk
Seasonal outdoor pool, pool umbrellas, sun loungers
Kenny's Tipperary Inn

Kenny's Tipperary Inn

2.0 star property
Culloden Shores
8.4 out of 10, Very Good, (878)
"Really clean and nice location"
United States
Tiara
Kenny's Tipperary Inn
Exterior
Montauk Manor

Montauk Manor

3.5 star property
Montauk
9.2 out of 10, Wonderful, (1265)
"Great ambience. Very kind and friendly service. Wonderful luxe suite. Very homey and cozy. I really enjoyed my stay here. Just lovely. "
United States
Violet
The price is SAR 520
SAR 668 total
includes taxes & fees
8 Dec - 9 Dec
Montauk Manor
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2.0 star property
Southampton
9.6 out of 10, Exceptional, (390)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
The price is SAR 414
SAR 477 total
includes taxes & fees
22 Dec - 23 Dec
The Bentley Hotel Southampton
Seasonal outdoor pool, open 8:00 AM to 7:00 PM, sun loungers
The Harbor Front Inn

The Harbor Front Inn

3.5 star property
Greenport
8.8 out of 10, Excellent, (540)
"Awesome stay!!! Great Location "
United States
Bryan
The price is SAR 492
SAR 746 total
includes taxes & fees
29 Dec - 30 Dec
The Harbor Front Inn
Exterior
Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook

2.0 star property
Old Saybrook
7.2 out of 10, Good, (460)
"🙂"
United States
Jared
The price is SAR 252
SAR 289 total
includes taxes & fees
5 Jan - 6 January 2026
Econo Lodge Inn & Suites Old Saybrook Westbrook
Seasonal outdoor pool
Clinton Motel

Clinton Motel

2.5 star property
Clinton
8.6 out of 10, Excellent, (296)
"Great staff and clean rooms"
United States
Tyler
The price is SAR 293
SAR 337 total
includes taxes & fees
8 Dec - 9 Dec
Clinton Motel
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Hamlet Inn

Hamlet Inn

2.0 star property
Southampton
8.6 out of 10, Excellent, (439)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is SAR 385
SAR 498 total
includes taxes & fees
18 Dec - 19 Dec
Hamlet Inn
Indoor pool, open 9:00 AM to 9:00 PM, sun loungers
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 star property
Old Saybrook
7.8 out of 10, Good, (1001)
"Staff was kind. Easy, comfortable stay."
United States
Jake
The price is SAR 380
SAR 437 total
includes taxes & fees
14 Dec - 15 Dec
Quality Inn Old Saybrook - Westbrook
Outdoor pool, sun loungers
Daunt's Albatross Motel

Daunt's Albatross Motel

2.0 star property
Downtown Montauk
9.0 out of 10, Wonderful, (287)
"The staff is the best, made my birthday stay extra special. Love the room and how clean and cute it was. Best hotel in town."
United States
Tiffany
Daunt's Albatross Motel
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

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"Lovely rooms and loved the fireplace. Great stay. Awesome few days away from real life!"
Andrew 2-night trip
Posted 5 days ago
Saybrook Point Resort & Marina

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Frequently asked questions

What are some accommodations with pools in Shelter Island?
Gurney's Montauk Resort & Seawater Spa: Features a seasonal outdoor pool, an indoor pool, and a private beach. Montauk Blue Hotel: Offers sun loungers, an indoor pool, and complimentary wireless internet access. Sound View Greenport: Provides a private beach, a seasonal outdoor pool, and 2 bars. Quality Inn Old Saybrook - Westbrook: Features buffet, an indoor pool, and free self parking. Saybrook Point Resort & Marina: 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 Mashomack Preserve. Discover sights such as Shelter Island Historical Society, Shelter Island Whale's Tail, and Crescent Beach 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.