Hotels with Pool & Resorts in Shelter Island from AU$126

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Check availability on Shelter Island Hotels with Pool

Tonight
1 Feb - 2 Feb
Tomorrow
2 Feb - 3 Feb
Next weekend
6 Feb - 8 Feb
In two weeks
13 Feb - 15 Feb

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, (1,290 reviews)
"Nice pool, great restaurant "
United States
April
The price is AU$256
includes taxes & fees
4 Feb - 5 Feb
Montauk Manor
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, (608 reviews)
"Nice place"
United States
Mateusz
The price is AU$261
includes taxes & fees
3 Feb - 4 Feb
Sound View Greenport
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
Outdoor pool

Offshore Montauk

Offshore Montauk
2.0 star property
Montauk
9.4 out of 10, Exceptional, (98 reviews)
"Hotel was beautiful !!"
United States
Erica
The price is AU$273
includes taxes & fees
16 Feb - 17 Feb
Offshore Montauk
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, (563 reviews)
"Everything was Great Immaculate hotel very good location sraff was great"
United States
latoya
The price is AU$261
includes taxes & fees
3 Feb - 4 Feb
The Harbor Front Inn
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, (1,001 reviews)
"Tamara, who checked us in, made a great first impression. She was friendly, helpful, and very accommodating."
United States
Kameron
The price is AU$188
includes taxes & fees
11 Feb - 12 Feb
Hyatt Place Long Island East End
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas

Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (448 reviews)
"Room was in good condition however I found the shower to be extremely small despite having great water pressure and extremely nice temperature."
United States
gail
The price is AU$160
includes taxes & fees
3 Feb - 4 Feb
Hamlet Inn
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, (432 reviews)
"Adorable room"
United States
Martin
The price is AU$181
includes taxes & fees
8 Feb - 9 Feb
The Bentley Hotel Southampton
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 AU$167
includes taxes & fees
8 Feb - 9 Feb
Quality Inn Old Saybrook - Westbrook
Exterior

Southampton Long Island Hotel

Southampton Long Island Hotel
2.5 star property
Southampton
8.6 out of 10, Excellent, (206 reviews)
"Staff was amazing. The room was very clean. I've stayed here numerous times, even on the night before my wedding as I was married in the Hamptons and I highly recommend! "
United States
Martine
The price is AU$180
includes taxes & fees
3 Feb - 4 Feb
Southampton Long Island Hotel
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

Beach
Indoor pool

Top Shelter Island Hotel Reviews

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

10/10 Excellent
"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. "
Kathleen 1-night trip
Posted 5 days ago
Quality Inn Old Saybrook - Westbrook

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.