Hotels with Swimming Pool in Shelter Island, New York

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Check availability on Shelter Island Hotels with Swimming Pool

Tonight
Jan 8 - Jan 9
Tomorrow
Jan 9 - Jan 10
This weekend
Jan 9 - Jan 11
Next weekend
Jan 16 - Jan 18

Our top choices for Shelter Island hotels with a pool

Seasonal outdoor pool, pool umbrellas, sun 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, (882)
"Really clean and nice location"
United States
Tiara
Kenny's Tipperary Inn
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, (447)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is P5,114
P6,610 total
includes taxes & fees
Jan 11 - Jan 12
Hamlet Inn
Exterior
Montauk Manor

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1281)
"Very beautiful place, staff are amazing. Thank you"
United States
Frank
The price is P8,204
P10,531 total
includes taxes & fees
Jan 14 - Jan 15
Montauk Manor
Seasonal outdoor pool
Clinton Motel

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (299)
"Is good"
United States
Miguel
The price is P4,511
P5,188 total
includes taxes & fees
Jan 10 - Jan 11
Clinton Motel
Outdoor pool
Offshore Montauk

Offshore Montauk

Offshore Montauk
2.0 star property
Montauk
9.4 out of 10, Exceptional, (93)
"Hotel was beautiful !!"
United States
Erica
The price is P6,872
P11,232 total
includes taxes & fees
Feb 8 - Feb 9
Offshore Montauk
Seasonal outdoor pool, open 8:00 AM to 7:00 PM, sun loungers
The Harbor Front Inn

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (560)
"Everything was Great Immaculate hotel very good location sraff was great"
United States
latoya
The price is P7,963
P10,793 total
includes taxes & fees
Jan 13 - Jan 14
The Harbor Front Inn
Exterior
Southampton Long Island Hotel

Southampton Long Island Hotel

Southampton Long Island Hotel
2.5 star property
Southampton
8.6 out of 10, Excellent, (206)
"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 P6,215
P7,411 total
includes taxes & fees
Jan 10 - Jan 11
Southampton Long Island Hotel
Individually decorated, individually furnished, desk, laptop workspace
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, (466)
"All good it met our expectations as a budget hotel. Large clean room bed was comfortable although the pillows were past it. "
United States
Hilary
The price is P3,968
P4,563 total
includes taxes & fees
Jan 20 - Jan 21
Econo Lodge Inn & Suites Old Saybrook Westbrook
Seasonal outdoor pool, pool umbrellas, sun loungers
Sound View Greenport

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.6 out of 10, Excellent, (604)
"Nice place"
United States
Mateusz
The price is P8,743
P11,680 total
includes taxes & fees
Feb 1 - Feb 2
Sound View Greenport
Indoor pool, open 9:00 AM to 9:00 PM, sun loungers
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1001)
"The very friendly staff made this stay enjoyable from The beginning. The hotel was very clean and comfy. "
United States
Virginia
The price is P5,736
P6,596 total
includes taxes & fees
Jan 20 - Jan 21
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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Top Shelter Island Hotel Reviews

Hyatt Place Long Island East End

Hyatt Place Long Island East End

10/10 Excellent
"Clean and quiet. "
Jeffrey 1-night trip
Posted 4 days ago
Hyatt Place Long Island East End

Frequently asked questions

What are some accommodations 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. Montauk Blue Hotel: Provides sun loungers, an indoor pool, and complimentary wireless internet access. Pier Blue Inn Old Saybrook - Essex: Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. The Bentley Hotel Southampton: 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 Whale's Tail, Crescent Beach, 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 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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