Search Hotels with Pool in Shelter Island

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Check availability on Shelter Island Hotels with Pool

Tonight
30 Dec - 31 Dec
Tomorrow
31 Dec - 1 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Shelter Island hotels with a pool

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 ฿7,541
฿11,771 total
includes taxes & fees
31 Dec - 1 Jan 2026
Hero Beach Club
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 ฿4,301
฿5,522 total
includes taxes & fees
5 Jan - 6 Jan 2026
Montauk Manor
Seasonal outdoor pool, pool umbrellas, pool loungers
Journey East Hampton

Journey East Hampton

Journey East Hampton
4.0 star property
East Hampton North
9.0 out of 10, Wonderful, (160)
"We were able to access many beaches with the beach pass that came with the stay. That was the main reason we wanted to stay there. The rooms were very nice, spacious and comfortable. "
United States
Sarah
Journey East Hampton
Outdoor pool, pool 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, (291)
"Daunts is our home away from home when we visit Montauk. From the convenience to the superb hospitality and comfortable rooms. If you’re visiting MTK you have to stay at Daunts, and their pet friendly "
United States
Yohayna
Daunt's Albatross Motel
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 ฿2,709
฿3,502 total
includes taxes & fees
1 Jan - 2 Jan 2026
Hamlet Inn
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, (880)
"Really clean and nice location"
United States
Tiara
Kenny's Tipperary Inn
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, (554)
"Room and staff were amazing. "
United States
Manuel
The price is ฿4,278
฿5,678 total
includes taxes & fees
29 Jan - 30 Jan 2026
The Harbor Front Inn
Aerial view
Southampton Inn

Southampton Inn

Southampton Inn
3.0 star property
Southampton
8.6 out of 10, Excellent, (553)
"Beautiful small hotel with lots of parking , beautiful area "
United States
David
The price is ฿6,207
฿7,597 total
includes taxes & fees
5 Jan - 6 Jan 2026
Southampton Inn
Graybarn Cottage | Room amenity
Mill House Inn

Mill House Inn

Mill House Inn
5.0 star property
Pantigo Road Historic District
9.0 out of 10, Wonderful, (76)
"the rooms are outdated and the front desk staff was overbearing the location is great but it’s noisy the breakfast was awesome as was the chef "
United States
Sharon
The price is ฿15,034
฿18,894 total
includes taxes & fees
31 Dec - 1 Jan 2026
Mill House Inn
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 ฿3,817
฿4,392 total
includes taxes & fees
22 Jan - 23 Jan 2026
The Bentley Hotel Southampton
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 2 weeks ago
Gurney's Montauk Resort & Seawater Spa
The Atlantic Hotel

The Atlantic Hotel

10/10 Excellent
"Great hotel for a quick stay - very friendly staff"
Dianne 1-night trip
Posted 1 month ago
The Atlantic Hotel

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. 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 sunloungers, 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 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.