Search Hotels with Pool in Shelter Island

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Check availability on Shelter Island Hotels with Pool

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, (306 reviews)
  • cleanliness
    Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
The price is ฿2,499
฿2,874 total
includes taxes & fees
15 Apr - 16 Apr
Clinton Motel
Indoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, pool loungers

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,006 reviews)
  • cleanliness
    Plunge into pool paradise at this welcoming hotel with sun loungers and a relaxing indoor retreat.
The price is ฿3,241
฿3,727 total
includes taxes & fees
19 Apr - 20 Apr
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, (470 reviews)
  • cleanliness
    Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodation.
The price is ฿2,292
฿2,635 total
includes taxes & fees
19 Apr - 20 Apr
Econo Lodge Inn & Suites 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 ฿5,959
฿6,808 total
includes taxes & fees
14 Apr - 15 Apr
North Fork Cottages & RV Resort
Seasonal outdoor pool, pool 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 ฿4,005
฿4,576 total
includes taxes & fees
3 May - 4 May
Ocean Resort 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, (469 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 ฿3,575
฿4,621 total
includes taxes & fees
16 Apr - 17 Apr
Hamlet Inn
Outdoor pool

Offshore Montauk

Offshore Montauk
4.5 star property
Montauk
9.4 out of 10, Exceptional, (123 reviews)
The price is ฿5,508
฿9,953 total
includes taxes & fees
20 Apr - 21 Apr
Offshore Montauk
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 ฿4,613
฿6,663 total
includes taxes & fees
29 Apr - 30 Apr
Cliffside Resort Condominiums
Front of property

Beach Plum Resort

Beach Plum Resort
3.0 star property
Montauk
9.0 out of 10, Wonderful, (161 reviews)
  • cleanliness
    Outdoor pool paradise offers relaxation and sunshine after coastal adventures.
The price is ฿6,289
฿7,882 total
includes taxes & fees
12 May - 13 May
Beach Plum 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

Sound View Greenport

Sound View Greenport

10/10 Excellent
"Loved our stay. Our room was gorgeous a s in the perfect location. Would recommend and plan on coming back in the future!"
Tara 2-night trip
Posted 11 hours ago
Sound View Greenport

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. 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 Historical Society and Havens House 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.