Hotels with Swimming Pools in Shelter Island

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Check availability on Shelter Island Hotels with Swimming Pools

Tonight
4 Jan - 5 Jan
Tomorrow
5 Jan - 6 Jan
Next weekend
9 Jan - 11 Jan
In two weeks
16 Jan - 18 Jan

Our top choices for Shelter Island hotels with a pool

BBQ/picnic Area
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 S$244
includes taxes & fees
19 Jan - 20 Jan
Offshore Montauk
Exterior
Montauk Manor

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1279)
"Very beautiful place, staff are amazing. Thank you"
United States
Frank
The price is S$229
includes taxes & fees
6 Jan - 7 Jan
Montauk Manor
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, (882)
"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, (558)
"Room and staff were amazing. "
United States
Manuel
The price is S$235
includes taxes & fees
1 Feb - 2 Feb
The Harbor Front Inn
Exterior
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, (465)
"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 S$99
includes taxes & fees
14 Jan - 15 Jan
Econo Lodge Inn & Suites Old Saybrook Westbrook
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 S$145
includes taxes & fees
6 Jan - 7 Jan
Hamlet Inn
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 S$112
includes taxes & fees
6 Jan - 7 Jan
Clinton Motel
Seasonal outdoor pool, pool umbrellas, pool loungers
Sound View Greenport

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.6 out of 10, Excellent, (603)
"Nice place"
United States
Mateusz
The price is S$269
includes taxes & fees
14 Jan - 15 Jan
Sound View Greenport
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, (417)
"Adorable boutique hotel with charming unique touches. "
United States
Mary
The price is S$182
includes taxes & fees
22 Jan - 23 Jan
The Bentley Hotel Southampton
Indoor pool, outdoor pool
Hyatt Place Long Island East End

Hyatt Place Long Island East End

Hyatt Place Long Island East End
3.0 star property
Riverhead
9.2 out of 10, Wonderful, (1002)
"Loved this hotel. Rooms were spacious and clean and the area is very quaint!"
United States
Ryan
The price is S$156
includes taxes & fees
20 Jan - 21 Jan
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

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"Every time we go here it’s fantastic. The hotel is undergoing a renovation that will be completed the summer of 27. The rooms will have updated Wi-Fi and several other upgrades. This is still a fantastic destination. especially in the summer when you can sit outside and look at all the boats and enjoy a nice cold cocktail."
Mark 1-night trip
Posted 3 days ago
Saybrook Point Resort & Marina

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. Montauk Blue Hotel: Provides sunloungers, an indoor pool and complimentary wireless Internet access. Pier Blue Inn Old Saybrook - Essex: Offers free self parking, an outdoor pool and complimentary wireless Internet access. Offshore Montauk: Features free self parking, a seasonal 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 Crescent Beach, Gardiner's Bay Country Club and Shelter Island Historical Society 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.

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