Shelter Island Hotels with Swimming Pool

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Check availability on Shelter Island Hotels with Swimming Pools

Our top choices for Shelter Island hotels with a pool

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (309 reviews)
  • cleanliness
    Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
The price is RM307
RM353 total
includes taxes & fees
14 May - 15 May
Clinton Motel

Ocean Resort Inn

Ocean Resort Inn
2.0 star property
Downtown Montauk
9.6 out of 10, Exceptional, (492 reviews)
  • cleanliness
    Soak in coastal charm at the heated saltwater pool steps from Montauk's sandy shores.
The price is RM530
RM605 total
includes taxes & fees
20 May - 21 May
Ocean Resort Inn

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, (473 reviews)
  • cleanliness
    Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodation.
The price is RM316
RM363 total
includes taxes & fees
20 May - 21 May
Econo Lodge Inn & Suites Old Saybrook Westbrook

The Penny Lane

The Penny Lane
2.0 star property
Hampton Bays
9.0 out of 10, Wonderful, (77 reviews)
  • cleanliness
    Seasonal poolside relaxation awaits at this oceanfront hotel with sun loungers, umbrellas, and gardens.
The price is RM885
RM1,011 total
includes taxes & fees
17 May - 18 May
The Penny Lane

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
9.0 out of 10, Wonderful, (14 reviews)
The price is RM1,039
RM1,187 total
includes taxes & fees
17 May - 18 May
North Fork Cottages & RV Resort

Sun N Sound

Sun N Sound
2.5 star property
Culloden Shores
9.0 out of 10, Wonderful, (269 reviews)
  • cleanliness
    Splash into refreshing waters at this beach-adjacent retreat with sun-soaked outdoor pool.
The price is RM398
RM519 total
includes taxes & fees
18 May - 19 May
Sun N Sound

Marram

Marram
4.0 star property
Montauk
8.8 out of 10, Excellent, (253 reviews)
  • cleanliness
    Cool ocean-adjacent pool getaway with loungers, umbrellas, and beach perks for the perfect summer splash.
The price is RM806
RM1,707 total
includes taxes & fees
19 May - 20 May
Marram

Aqualina Inn Montauk

Aqualina Inn Montauk
2.5 star property
Downtown Montauk
9.6 out of 10, Exceptional, (496 reviews)
  • cleanliness
    Dive into poolside luxury at this Montauk motel with summer splash fun and garden views.
The price is RM530
RM605 total
includes taxes & fees
20 May - 21 May
Aqualina Inn Montauk

Offshore Montauk

Offshore Montauk
4.0 star property
Montauk
9.4 out of 10, Exceptional, (132 reviews)
The price is RM893
RM1,469 total
includes taxes & fees
26 May - 27 May
Offshore Montauk

Ocean Surf Resort

Ocean Surf Resort
2.0 star property
Downtown Montauk
8.4 out of 10, Very good, (241 reviews)
  • cleanliness
    Seasonal Montauk retreat with sun-drenched pool deck offering ocean views, just steps from city centre.
The price is RM859
RM982 total
includes taxes & fees
21 May - 22 May
Ocean Surf 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.

Choose what matters most at hotels with a pool in Shelter Island

Top Shelter Island Hotel Reviews

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. Montauk Yacht Club: Hotel, 5-minute walk from The Hamptons Beaches. Provides 2 outdoor swimming pools, a children's pool and a private beach. The Bentley Hotel Southampton: Features free self parking, a seasonal outdoor pool and complimentary wireless Internet access. Pier Blue Inn Old Saybrook - Essex: Features a private beach, a seasonal 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, Mashomack Preserve and Shell Beach 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.

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