Search Hotels with Swimming Pool in Shelter Island

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Check availability on Shelter Island Hotels with Swimming Pool

Our top choices for Shelter Island hotels with a pool

Outdoor pool
Offshore Montauk

Offshore Montauk

Offshore Montauk
2.0 star property
Montauk
9.2 out of 10, Wonderful, (77)
"Nice decoration, clean amenities, good stay"
United States
weihao
The price is ₹10,436
₹17,057 total
includes taxes & fees
1 Jan - 2 Jan 2026
Offshore Montauk
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, (878)
"Really clean and nice location"
United States
Tiara
Kenny's Tipperary Inn
Exterior
Montauk Manor

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1265)
"Great ambience. Very kind and friendly service. Wonderful luxe suite. Very homey and cozy. I really enjoyed my stay here. Just lovely. "
United States
Violet
The price is ₹12,458
₹15,992 total
includes taxes & fees
11 Dec - 12 Dec
Montauk Manor
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, (392)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
The price is ₹10,276
₹11,830 total
includes taxes & fees
14 Dec - 15 Dec
The Bentley Hotel Southampton
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, (440)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is ₹8,009
₹10,351 total
includes taxes & fees
12 Dec - 13 Dec
Hamlet 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, (544)
"Awesome stay!!! Great Location "
United States
Bryan
The price is ₹11,786
₹17,864 total
includes taxes & fees
24 Dec - 25 Dec
The Harbor Front Inn
Seasonal outdoor pool, pool umbrellas, pool loungers
Hero Beach Club

Hero Beach Club

Hero Beach Club
4.0 star property
Montauk
9.0 out of 10, Wonderful, (202)
"Great weekend trip "
United States
Timothy
The price is ₹12,865
₹23,837 total
includes taxes & fees
18 Dec - 19 Dec
Hero Beach Club
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, (460)
"🙂"
United States
Jared
The price is ₹6,025
₹6,929 total
includes taxes & fees
16 Dec - 17 Dec
Econo Lodge Inn & Suites Old Saybrook Westbrook
Seasonal outdoor pool
Clinton Motel

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (296)
"Great staff and clean rooms"
United States
Tyler
The price is ₹7,011
₹8,063 total
includes taxes & fees
11 Dec - 12 Dec
Clinton Motel
Exterior
Daunt's Albatross Motel

Daunt's Albatross Motel

Daunt's Albatross Motel
2.0 star property
Downtown Montauk
9.0 out of 10, Wonderful, (288)
"The staff is the best, made my birthday stay extra special. Love the room and how clean and cute it was. Best hotel in town."
United States
Tiffany
The price is ₹15,066
₹17,214 total
includes taxes & fees
1 Jan - 2 Jan 2026
Daunt's Albatross Motel
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.
View all properties

Top Shelter Island Hotel Reviews

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"My stay with Saybrook Point Resort & Marina was amazing. Clean room, amazing staff and amenities! I plan to return again!"
Michelle 2-night trip
Posted 2 days ago
Saybrook Point Resort & Marina

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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. Pier Blue Inn Old Saybrook - Essex: Provides a seasonal outdoor pool, an indoor pool and a private beach. Water's Edge Resort & Spa: Features a private beach, a seasonal outdoor pool and 2 bars. Sound View Greenport: Offers sunloungers, an indoor pool and complimentary wireless Internet access. Montauk Blue Hotel: Features 2 outdoor swimming pools, an indoor pool and a full-service spa.
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 Historical Society, Shelter Island Whale's Tail and Mashomack Preserve 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.