Search Hotels with Pool in Shelter Island

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Check availability on Shelter Island Hotels with Pool

Our top choices for Shelter Island hotels with a pool

Exterior

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,293 reviews)
"Nice pool, great restaurant "
United States
April
The price is Rp2.329.173
Rp2.989.946 total
includes taxes & fees
17 Feb - 18 Feb
Montauk Manor
Outdoor pool

Offshore Montauk

Offshore Montauk
2.0 star property
Montauk
9.4 out of 10, Exceptional, (102 reviews)
"Hotel was beautiful !!"
United States
Erica
The price is Rp1.951.061
Rp3.189.073 total
includes taxes & fees
24 Feb - 25 Feb
Offshore Montauk
Seasonal outdoor pool, pool umbrellas, pool loungers

Kenny's Tipperary Inn

Kenny's Tipperary Inn
2.0 star property
Culloden Shores
8.4 out of 10, Very good, (885 reviews)
"Big room Clean Needs bathroom update In general, we had a good day"
United States
Raz
Kenny's Tipperary Inn
Seasonal outdoor pool, pool umbrellas, pool loungers

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (610 reviews)
"Nice place"
United States
Mateusz
The price is Rp2.570.501
Rp3.416.749 total
includes taxes & fees
24 Feb - 25 Feb
Sound View Greenport
Seasonal outdoor pool, open 8:00 AM to 7:00 PM, pool loungers

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (566 reviews)
"Lovely hotel with great location in town. Great free breakfast and wonderful staff. We will return! "
United States
Pamela
The price is Rp2.102.305
Rp2.881.835 total
includes taxes & fees
17 Feb - 18 Feb
The Harbor Front Inn
Seasonal outdoor pool

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (305 reviews)
"Quiet place, went off season, cooked all meals in the room, good home base to explore the area."
United States
Jerry
The price is Rp2.214.227
Rp2.895.333 total
includes taxes & fees
18 Feb - 19 Feb
Windward Shores Ocean Resort
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (434 reviews)
"Adorable room"
United States
Martin
The price is Rp2.119.551
Rp2.438.392 total
includes taxes & fees
17 Feb - 18 Feb
The Bentley Hotel Southampton
Seasonal outdoor pool

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (302 reviews)
"The room was comfortable and clean. A good value for the money."
United States
Michael
The price is Rp1.310.790
Rp1.507.409 total
includes taxes & fees
16 Feb - 17 Feb
Clinton Motel
Indoor pool, outdoor pool

Hyatt Place Long Island East End

Hyatt Place Long Island East End
3.0 star property
Riverhead
9.2 out of 10, Wonderful, (1,004 reviews)
"Tamara, who checked us in, made a great first impression. She was friendly, helpful, and very accommodating."
United States
Kameron
The price is Rp1.891.237
Rp2.160.739 total
includes taxes & fees
16 Feb - 17 Feb
Hyatt Place Long Island East End
Indoor pool, open 9:00 AM to 9:00 PM, pool loungers

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,001 reviews)
"Hotel was very clean, staff was wonderful and the pool was so relaxing. It was a quick visit but definitely would stay again if I was in that area. "
United States
Kathleen
The price is Rp1.699.826
Rp1.954.800 total
includes taxes & fees
18 Feb - 19 Feb
Quality Inn 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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Choose what matters most at hotels with a pool in Shelter Island

Breakfast included
Sea view

Top Shelter Island Hotel Reviews

Frequently asked questions

What are some accommodation options with pools in Shelter Island?
Gurney's Montauk Resort & Seawater Spa: Resort, 13-minute walk from The Hamptons Beaches. Features a seasonal outdoor pool, an indoor pool and a private beach. Pier Blue Inn Old Saybrook - Essex: Hotel, 1-minute walk from The Hamptons Beaches. Provides sunloungers, an indoor pool and complimentary wireless Internet access. Montauk Blue Hotel: Features a private beach, a seasonal outdoor pool and 2 bars. Sound View Greenport: Aparthotel, 14-minute walk from The Hamptons Beaches. Offers a seasonal outdoor pool, an indoor pool and 3 outdoor tennis courts. Montauk Manor: Features a seasonal outdoor pool, an indoor pool and a private beach.
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 Whale's Tail, Mashomack Preserve and Shell 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.