Find Hotels with a Pool in Shelter Island, NY

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Check availability on Shelter Island Hotels with a Pool

Tonight
Dec 29 - Dec 30
Tomorrow
Dec 30 - Dec 31
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

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, (89)
"Hotel was beautiful !!"
United States
Erica
The price is ￥18,178
￥29,713 total
includes taxes & fees
Jan 11 - Jan 12, 2026
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, (880)
"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, (1274)
"The room was very clean, comfortable and quiet. The hotel was decorated beautifully for the holidays. The pool area with hot tub was clean and enjoyable "
United States
Kathleen
The price is ￥21,701
￥27,858 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Montauk Manor
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, (445)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is ￥13,950
￥18,030 total
includes taxes & fees
Dec 30 - Dec 31
Hamlet Inn
Outdoor pool, a heated pool
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Water Mill
10.0 out of 10, Exceptional, (6)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
United States
Stephanie M.
The price is ￥656,373
￥1,157,219 total
includes taxes & fees
Jan 6 - Jan 7, 2026
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Seasonal outdoor pool
Clinton Motel

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (298)
"Great staff and clean rooms"
United States
Tyler
The price is ￥12,212
￥14,044 total
includes taxes & fees
Dec 30 - Dec 31
Clinton Motel
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, (412)
"Adorable boutique hotel with charming unique touches. "
United States
Mary
The price is ￥19,591
￥22,540 total
includes taxes & fees
Jan 4 - Jan 5, 2026
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

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (554)
"Room and staff were amazing. "
United States
Manuel
The price is ￥21,161
￥28,434 total
includes taxes & fees
Jan 28 - Jan 29, 2026
The Harbor Front Inn
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, (463)
"We came in for a family wedding in the area and this hotel was a great location. The mexican restaurant that was down the street is fantastic, great margaritas ! Would definitely use this location again if we were out this way. Thank you for a wonderful stay !"
United States
Robert
The price is ￥10,495
￥12,069 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Econo Lodge Inn & Suites Old Saybrook Westbrook
Seasonal outdoor pool, pool umbrellas, sun loungers
Sound View Greenport

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very Good, (601)
"Great view but a gas station has a better breakfast. "
United States
Michael
The price is ￥24,926
￥32,737 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Sound View Greenport
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
"Good room. Great view! Nice heating system. Friendly staff. "
Jessie 1-night trip
Posted 2 days ago
Gurney's Montauk Resort & Seawater Spa

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. Water's Edge Resort & Spa: Offers a seasonal outdoor pool, an indoor pool, and a private beach. Sound View Greenport: Provides a private beach, a seasonal outdoor pool, and 2 bars. Montauk Blue Hotel: Features sun loungers, an indoor pool, and complimentary wireless internet access. Pier Blue Inn Old Saybrook - Essex: Features free self parking, an outdoor pool, and complimentary wireless internet access.
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.

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