Search Hotels with Pool in Shelter Island

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Our top choices for Shelter Island hotels with a pool

Offshore Montauk

Offshore Montauk
2.0 star property
Montauk
9.4 out of 10, Exceptional, (85)
"Hotel was beautiful !!"
United States
Erica
The price is 3.051.340 ₫
4.987.516 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Offshore Montauk

Kenny's Tipperary Inn

Kenny's Tipperary Inn
2.0 star property
Culloden Shores
8.4 out of 10, Very good, (879)
"Really clean and nice location"
United States
Tiara
Kenny's Tipperary Inn

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1272)
"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 3.642.685 ₫
4.676.094 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Montauk Manor

Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (444)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is 2.344.756 ₫
3.030.551 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Hamlet Inn

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 2.049.996 ₫
2.357.495 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Clinton Motel

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (405)
"Room was beautiful and spacious. Staff was courteous and on point. "
United States
Ron
The price is 3.288.550 ₫
3.783.450 ₫ total
includes taxes & fees
9 Jan - 10 Jan 2026
The Bentley Hotel Southampton

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (549)
"Awesome stay!!! Great Location "
United States
Bryan
The price is 3.552.012 ₫
4.772.780 ₫ total
includes taxes & fees
25 Jan - 26 Jan 2026
The Harbor Front Inn

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 1.761.682 ₫
2.025.934 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Econo Lodge Inn & Suites Old Saybrook Westbrook

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.6 out of 10, Excellent, (600)
"Staff was amazing , room clean view phenomenal "
United States
Denise
The price is 3.410.769 ₫
4.611.410 ₫ total
includes taxes & fees
4 Jan - 5 Jan 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.

Top Shelter Island Hotel Reviews

Frequently asked questions

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 accommodation that has an outdoor pool if you'll be visiting Shelter Island in the hottest months of August, July or September, when the average temp is 21°C. Accommodation 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 3°C.