Hotels with Pool & Resorts in Shelter Island from AU$116

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Check availability on Shelter Island Hotels with Pool

Our top choices for Shelter Island hotels with a pool

Seasonal outdoor pool, pool umbrellas, pool 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
The price is AU$207
includes taxes & fees
4 Jan - 5 Jan 2026
Kenny's Tipperary Inn
Exterior
Montauk Manor

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1268)
"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 AU$268
includes taxes & fees
18 Dec - 19 Dec
Montauk Manor
BBQ/picnic Area
Offshore Montauk

Offshore Montauk

Offshore Montauk
2.0 star property
Montauk
9.2 out of 10, Wonderful, (81)
"Nice decoration, clean amenities, good stay"
United States
weihao
The price is AU$286
includes taxes & fees
1 Jan - 2 Jan 2026
Offshore Montauk
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, (443)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is AU$174
includes taxes & fees
18 Dec - 19 Dec
Hamlet Inn
Seasonal outdoor pool
Clinton Motel

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (297)
"Great staff and clean rooms"
United States
Tyler
The price is AU$135
includes taxes & fees
16 Jan - 17 Jan 2026
Clinton Motel
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 AU$11,264
includes taxes & fees
18 Dec - 19 Dec
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Seasonal outdoor pool, open 8:00 AM to 7:00 PM, pool loungers
The Harbor Front Inn

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (547)
"Awesome stay!!! Great Location "
United States
Bryan
The price is AU$305
includes taxes & fees
18 Dec - 19 Dec
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 AU$400
includes taxes & fees
28 Dec - 29 Dec
Hero Beach Club
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, (398)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
The price is AU$217
includes taxes & fees
4 Jan - 5 Jan 2026
The Bentley Hotel Southampton
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 AU$116
includes taxes & fees
4 Jan - 5 Jan 2026
Econo Lodge Inn & Suites Old Saybrook Westbrook
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 was perfect. Staff, room, experience. Will definitely stay again. "
Kristy 1-night trip
Posted 3 days ago
Gurney's Montauk Resort & Seawater Spa

Frequently asked questions

What are some accommodation options 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 sunloungers, an indoor pool and complimentary wireless Internet access. Montauk Blue Hotel: Features 2 outdoor swimming 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 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.