Find Hotels with a Pool in Shelter Island, NY

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Check availability on Shelter Island Hotels with a Pool

Tonight
Apr 5 - Apr 6
Tomorrow
Apr 6 - Apr 7
Next weekend
Apr 10 - Apr 12
In two weeks
Apr 17 - Apr 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, (305 reviews)
  • cleanliness
    Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
The price is ￥12,135
￥13,955 total
includes taxes & fees
Apr 7 - Apr 8
Clinton Motel
Indoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,002 reviews)
  • cleanliness
    Plunge into pool paradise at this welcoming hotel with sun loungers and a relaxing indoor retreat.
The price is ￥16,151
￥18,573 total
includes taxes & fees
Apr 19 - Apr 20
Quality Inn Old Saybrook - Westbrook
Property map

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
8.6 out of 10, Excellent, (11 reviews)
The price is ￥31,441
￥35,921 total
includes taxes & fees
Apr 8 - Apr 9
North Fork Cottages & RV 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, (469 reviews)
  • cleanliness
    Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodations.
The price is ￥10,703
￥12,309 total
includes taxes & fees
Apr 12 - Apr 13
Econo Lodge Inn & Suites Old Saybrook Westbrook
Seasonal outdoor pool, sun loungers

Ocean Resort Inn

Ocean Resort Inn
2.0 star property
Downtown Montauk
9.6 out of 10, Exceptional, (487 reviews)
  • cleanliness
    Soak in coastal charm at the heated saltwater pool steps from Montauk's sandy shores.
The price is ￥19,959
￥22,804 total
includes taxes & fees
May 3 - May 4
Ocean Resort Inn
Outdoor pool

Offshore Montauk

Offshore Montauk
4.5 star property
Montauk
9.4 out of 10, Exceptional, (119 reviews)
The price is ￥28,311
￥50,587 total
includes taxes & fees
Apr 7 - Apr 8
Offshore Montauk
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, (465 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 ￥17,819
￥23,031 total
includes taxes & fees
Apr 16 - Apr 17
Hamlet Inn
Front of property

Beach Plum Resort

Beach Plum Resort
3.0 star property
Montauk
9.0 out of 10, Wonderful, (159 reviews)
  • cleanliness
    Outdoor pool paradise offers relaxation and sunshine after coastal adventures.
The price is ￥33,627
￥41,890 total
includes taxes & fees
Apr 12 - Apr 13
Beach Plum Resort
Seasonal outdoor pool, open 9:00 AM to 7:00 PM, pool umbrellas

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (249 reviews)
  • cleanliness
    Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
The price is ￥22,992
￥33,206 total
includes taxes & fees
Apr 29 - Apr 30
Cliffside Resort Condominiums
Front of property

Sea Crest Resort

Sea Crest Resort
2.5 star property
Amagansett
9.2 out of 10, Wonderful, (509 reviews)
  • cleanliness
    Coastal serenity awaits at this oceanfront hotel with an inviting pool and comfortable loungers for relaxation.
The price is ￥22,625
￥29,323 total
includes taxes & fees
Apr 23 - Apr 24
Sea Crest Resort
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

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

6/10 Okay
"Room was clean…ish. Food was alright but overpriced for what it was. Amenities were the highlight. Overall good experience but could have been had at much lower of a price tag."
Mohanram 2-night trip
Posted 9 hours ago
Gurney's Montauk Resort & Seawater Spa

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. Montauk Manor: Aparthotel, 14-minute walk from The Hamptons Beaches. Offers a seasonal outdoor pool, an indoor pool, and 3 outdoor tennis courts. Water's Edge Resort & Spa: Provides a seasonal outdoor pool, an indoor pool, and a private beach. Sound View Greenport: Features a private beach, a seasonal outdoor pool, and 2 bars. Hyatt Place Long Island East End: Offers an indoor pool, an outdoor pool, and 2 bars.
What is there to see and do in Shelter Island?
Surround yourself with nature at Sunset Beach and Crescent Beach. Discover sights such as Gardiner's Bay Country Club, Shelter Island Whale's Tail, 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 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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