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

Hotels with Swimming Pool in Shelter Island, New York

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Check availability on Shelter Island Hotels with Swimming Pool

Next weekend
Jul 10 - Jul 12
In two weeks
Jul 17 - Jul 19

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, (320 reviews)
  • cleanliness
    Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
The price is P5,467
P6,287 total
includes taxes & fees
Jul 6 - Jul 7
Clinton Motel
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 P7,258
P8,346 total
includes taxes & fees
Jul 26 - Jul 27
Quality Inn Old Saybrook - Westbrook
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, (482 reviews)
  • cleanliness
    Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodations.
The price is P4,947
P5,689 total
includes taxes & fees
Jul 12 - Jul 13
Econo Lodge Inn & Suites Old Saybrook Westbrook
Seasonal outdoor pool

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (26 reviews)
The price is P22,833
P26,086 total
includes taxes & fees
Jul 19 - Jul 20
North Fork Resort
Reception

The Penny Lane

The Penny Lane
3.0 star property
Hampton Bays
9.0 out of 10, Wonderful, (83 reviews)
  • cleanliness
    Seasonal poolside relaxation awaits at this oceanfront hotel with sun loungers, umbrellas, and gardens.
The price is P18,189
P20,781 total
includes taxes & fees
Jul 6 - Jul 7
The Penny Lane
Children's activities

Hampton's Vacation Inn

Hampton's Vacation Inn
2.5 star property
Hampton Bays
9.0 out of 10, Wonderful, (340 reviews)
  • cleanliness
    Soak in poolside bliss at this Hampton guesthouse with refreshing seasonal pool, tennis court, and nearby beach activities.
The price is P12,439
P14,212 total
includes taxes & fees
Jul 19 - Jul 20
Hampton's Vacation Inn
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, (486 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 P14,042
P18,150 total
includes taxes & fees
Jul 13 - Jul 14
Hamlet Inn
Seasonal outdoor pool

Budget Host East End

Budget Host East End
2.0 star property
Riverhead
6.8 out of 10, (828 reviews)
  • cleanliness
    Escape summer heat at this serene riverfront motel with a clean, seasonal pool.
The price is P7,679
P8,773 total
includes taxes & fees
Jul 8 - Jul 9
Budget Host East End
Seasonal outdoor pool

Ocean View Terrace Inn

Ocean View Terrace Inn
2.0 star property
Hampton Bays
8.6 out of 10, Excellent, (125 reviews)
  • cleanliness
    Beachside seasonal pool awaits with ocean adventures and relaxing massages nearby.
The price is P14,264
P20,708 total
includes taxes & fees
Jul 28 - Jul 29
Ocean View Terrace Inn
Seasonal outdoor pool, pool umbrellas, sun loungers

The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (91 reviews)
  • cleanliness
    Splash into coastal luxury at this beachfront hotel with a seasonal pool, spa, and private beach access.
The price is P46,424
P58,343 total
includes taxes & fees
Jul 12 - Jul 13
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

Aqualina Inn Montauk

Aqualina Inn Montauk

10/10 Excellent
"Clean room/ great staff/ walking distance to beach."
Joe 2-night trip
Posted 2 days ago
Aqualina Inn Montauk

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