Find Hotels with a Pool in Shelter Island, NY

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Check availability on Shelter Island Hotels with a Pool

Tonight
Jan 28 - Jan 29
Tomorrow
Jan 29 - Jan 30
This weekend
Jan 30 - Feb 1
Next weekend
Feb 6 - Feb 8

Our top choices for Shelter Island hotels with a pool

Outdoor pool

Offshore Montauk

Offshore Montauk
2.0 star property
Montauk
9.4 out of 10, Exceptional, (97 reviews)
"Hotel was beautiful !!"
United States
Erica
The price is NT$3,653
NT$5,971 total
includes taxes & fees
Feb 11 - Feb 12
Offshore Montauk
Exterior

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,287 reviews)
"The room was clean and nice. Breakfast was good and the service was great. The pool and Jacuzzi was nice and clean. We would definetly stay again. "
United States
Athena
The price is NT$4,361
NT$5,598 total
includes taxes & fees
Feb 5 - Feb 6
Montauk Manor
Seasonal outdoor pool, pool umbrellas, sun 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 NT$4,225
NT$5,727 total
includes taxes & fees
Feb 2 - Feb 3
Sound View Greenport
Seasonal outdoor pool, pool umbrellas, sun 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, open 8:00 AM to 7:00 PM, sun 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 NT$3,958
NT$5,421 total
includes taxes & fees
Jan 29 - Jan 30
The Harbor Front 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 boutique hotel with charming unique touches. "
United States
Mary
The price is NT$3,437
NT$3,959 total
includes taxes & fees
Feb 8 - Feb 9
The Bentley Hotel Southampton
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 NT$2,719
NT$3,514 total
includes taxes & fees
Feb 11 - Feb 12
Hamlet Inn
Indoor pool, open 9:00 AM to 9:00 PM, sun loungers

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,002 reviews)
"Room was very clean and staff was wonderful"
United States
Joseph
The price is NT$3,049
NT$3,506 total
includes taxes & fees
Feb 16 - Feb 17
Quality Inn Old Saybrook - Westbrook
Seasonal outdoor pool

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (301 reviews)
"The room was comfortable and clean. A good value for the money."
United States
Michael
The price is NT$2,391
NT$2,750 total
includes taxes & fees
Jan 29 - Jan 30
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, (1,006 reviews)
"Clean and quiet. "
United States
Jeffrey
The price is NT$3,511
NT$4,012 total
includes taxes & fees
Feb 11 - Feb 12
Hyatt Place Long Island East End
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

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

10/10 Excellent
"From the front desk to the rest of the staff, everyone was very friendly but also very professional and very helpful. I called the front desk about 5 straight times to ask questions I was waiting for the receptionist to e upset ,to my surprise she was laughing it up with me. That alone made my stay great"
PEDRO 1-night trip
Posted 6 days ago
Quality Inn Old Saybrook - Westbrook

Frequently asked questions

What are some accommodations 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 sun loungers, 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: Offers a seasonal outdoor pool, an indoor pool, and a private beach. Water's Edge Resort & Spa: Features an indoor pool, an outdoor pool, and 2 bars.
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 Whale's Tail, Crescent Beach, and Gardiner's Bay Country Club during your stay.
When is the best time to book a hotel with a pool in Shelter Island?
You may want to think about an accommodation that has an outdoor pool if you will be visiting Shelter Island in the hottest months of August, July, or September when the average temp is 70°F. Lodging 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 38°F.

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