Find Hotels with a Pool in Shelter Island, NY

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Check availability on Shelter Island Hotels with a Pool

Our top choices for Shelter Island hotels with a pool

BBQ/picnic area
Offshore Montauk

Offshore Montauk

Offshore Montauk
2.0 star property
Montauk
9.4 out of 10, Exceptional, (79)
"Nice decoration, clean amenities, good stay"
United States
weihao
The price is NT$3,622
NT$5,920 total
includes taxes & fees
Jan 8 - 2026/1/9
Offshore Montauk
Seasonal outdoor pool, pool umbrellas, sun loungers
Kenny's Tipperary Inn

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

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1266)
"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 NT$4,324
NT$5,550 total
includes taxes & fees
Dec 15 - Dec 16
Montauk Manor
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
The Bentley Hotel Southampton

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (393)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
The price is NT$3,542
NT$4,077 total
includes taxes & fees
Dec 14 - Dec 15
The Bentley Hotel Southampton
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Hamlet Inn

Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (440)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is NT$2,780
NT$3,593 total
includes taxes & fees
Dec 14 - Dec 15
Hamlet Inn
Seasonal outdoor pool, open 8:00 AM to 7:00 PM, sun loungers
The Harbor Front Inn

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (546)
"Amazing property, rooms, and staff. Book a room with a balcony for amazing views!"
United States
Matthew
The price is NT$4,090
NT$6,200 total
includes taxes & fees
Dec 25 - Dec 26
The Harbor Front Inn
Sports facility
Hero Beach Club

Hero Beach Club

Hero Beach Club
4.0 star property
Montauk
9.0 out of 10, Wonderful, (202)
"Great weekend trip "
United States
Timothy
The price is NT$4,465
NT$8,273 total
includes taxes & fees
Dec 18 - Dec 19
Hero Beach Club
Exterior
Econo Lodge Inn & Suites Old Saybrook Westbrook

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 NT$2,091
NT$2,405 total
includes taxes & fees
Jan 4 - 2026/1/5
Econo Lodge Inn & Suites Old Saybrook Westbrook
Seasonal outdoor pool
Clinton Motel

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 NT$2,433
NT$2,798 total
includes taxes & fees
Dec 14 - Dec 15
Clinton Motel
Outdoor pool, sun loungers
Daunt's Albatross Motel

Daunt's Albatross Motel

Daunt's Albatross Motel
2.0 star property
Downtown Montauk
9.0 out of 10, Wonderful, (288)
"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

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent
"EVERYTHING about our stay at Gurneys was wonderful. The staff was outstanding and so accommodating. The room was beautiful looking out at the ocean. We have decided to make a family tradition to go to stay."
Rachel 1-night trip
Posted 4 days ago
Gurney's Montauk Resort & Seawater Spa

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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. Pier Blue Inn Old Saybrook - Essex: Provides a seasonal outdoor pool, an indoor pool, and a private beach. Water's Edge Resort & Spa: Features a private beach, a seasonal outdoor pool, and 2 bars. Sound View Greenport: Offers sun loungers, an indoor pool, and complimentary wireless internet access. Montauk Blue Hotel: Features 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 Shelter Island Historical Society, Shelter Island Whale's Tail, and Mashomack Preserve 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.