A wooden gazebo by a pond with a large tree trunk nearby.

Shelter Island Hotels with Swimming Pool

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Check availability on Shelter Island Hotels with Swimming Pools

Next weekend
3 Jul - 5 Jul
In two weeks
10 Jul - 12 Jul

Our top choices for Shelter Island hotels with a pool

Seasonal outdoor pool

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (319 reviews)
  • cleanliness
    Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
The price is RM376
RM433 total
includes taxes & fees
29 Jun - 30 Jun
Clinton Motel
Seasonal outdoor pool

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.2 out of 10, Wonderful, (25 reviews)
The price is RM1,239
RM1,415 total
includes taxes & fees
29 Jun - 30 Jun
North Fork Resort
Individually decorated, individually furnished, desk, laptop workspace

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, (481 reviews)
  • cleanliness
    Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodation.
The price is RM329
RM379 total
includes taxes & fees
5 Jul - 6 Jul
Econo Lodge Inn & Suites Old Saybrook Westbrook
Lobby sitting area

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)
  • cleanliness
    Plunge into pool paradise at this welcoming hotel with sun loungers and a relaxing indoor retreat.
The price is RM483
RM556 total
includes taxes & fees
19 Jul - 20 Jul
Quality Inn Old Saybrook - Westbrook
Reception

The Penny Lane

The Penny Lane
3.0 star property
Hampton Bays
9.0 out of 10, Wonderful, (80 reviews)
  • cleanliness
    Seasonal poolside relaxation awaits at this oceanfront hotel with sun loungers, umbrellas, and gardens.
The price is RM1,090
RM1,245 total
includes taxes & fees
14 Jul - 15 Jul
The Penny Lane
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, (485 reviews)
  • cleanliness
    Serene seasonal pool retreat with private beach access just 2 miles away offers the perfect summer escape on Long Island.
The price is RM879
RM1,137 total
includes taxes & fees
6 Jul - 7 Jul
Hamlet Inn
Indoor pool, 2 outdoor pools, open 5:00 AM to 10:00 PM, pool umbrellas

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina
3.5 star property
Old Saybrook Center
9.6 out of 10, Exceptional, (1,001 reviews)
  • cleanliness
    Swim into serenity with three breathtaking pools and luxurious loungers for perfect poolside days at this resort.
The price is RM1,509
RM1,837 total
includes taxes & fees
21 Jul - 22 Jul
Saybrook Point Resort & Marina
Seasonal outdoor pool, open 9:00 AM to 7:00 PM, pool loungers

Hampton's Vacation Inn

Hampton's Vacation Inn
2.5 star property
Hampton Bays
9.0 out of 10, Wonderful, (339 reviews)
  • cleanliness
    Soak in poolside bliss at this Hampton guesthouse with refreshing seasonal pool, tennis court, and nearby beach activities.
The price is RM736
RM841 total
includes taxes & fees
29 Jun - 30 Jun
Hampton's Vacation Inn
Seasonal outdoor pool, pool umbrellas, pool loungers

The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (90 reviews)
  • cleanliness
    Splash into coastal luxury at this beachfront hotel with a seasonal pool, spa, and private beach access.
The price is RM2,419
RM3,040 total
includes taxes & fees
1 Jul - 2 Jul
The Pridwin 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

Breakfast included
4 stars

Top Shelter Island Hotel Reviews

Kenny's Tipperary Inn

Kenny's Tipperary Inn

10/10 Excellent
"Very pet friendly. Nice location and friendly staff. "
Ginger 1-night trip
Posted 2 days ago
Kenny's Tipperary Inn

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. Offshore Montauk: Hotel, 1-minute walk from The Hamptons Beaches. Offers a sauna, a seasonal outdoor pool and free self parking. Sound View Greenport: Provides a private beach, a seasonal outdoor pool and 2 bars. Montauk Manor: Aparthotel, 14-minute walk from The Hamptons Beaches. Features a seasonal outdoor pool, an indoor pool and 3 outdoor tennis courts. Pier Blue Inn Old Saybrook - Essex: Features a seasonal outdoor pool, an indoor pool and a private beach.
What is there to see and do in Shelter Island?
Explore places such as The Hamptons Beaches while you're in the area. Make a point to visit attractions such as Sunset Beach and Shelter Island Whale's Tail.
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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