Hotels with Swimming Pool in Shelter Island, New York

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Check availability on Shelter Island Hotels with Swimming 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, (311 reviews)
  • cleanliness
    Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
The price is P4,876
P5,607 total
includes taxes & fees
May 26 - May 27
Clinton Motel
View from property

Breakers Montauk

Breakers Montauk
3.0 star property
Montauk
8.6 out of 10, Excellent, (189 reviews)
  • cleanliness
    Seaside poolside escape with sun loungers and umbrellas creates a summer sanctuary.
The price is P5,932
P8,789 total
includes taxes & fees
May 27 - May 28
Breakers Montauk
Seasonal outdoor pool, sun loungers

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 P10,800
P12,340 total
includes taxes & fees
Jun 2 - Jun 3
Ocean Resort Inn
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, (474 reviews)
  • cleanliness
    Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodations.
The price is P4,970
P5,716 total
includes taxes & fees
Jun 1 - Jun 2
Econo Lodge Inn & Suites Old Saybrook Westbrook
Seasonal outdoor pool, sun loungers

Aqualina Inn Montauk

Aqualina Inn Montauk
2.5 star property
Downtown Montauk
9.6 out of 10, Exceptional, (497 reviews)
  • cleanliness
    Dive into poolside luxury at this Montauk motel with summer splash fun and garden views.
The price is P7,715
P8,814 total
includes taxes & fees
May 27 - May 28
Aqualina Inn Montauk
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, (1,000 reviews)
  • cleanliness
    Plunge into pool paradise at this welcoming hotel with sun loungers and a relaxing indoor retreat.
The price is P7,292
P8,386 total
includes taxes & fees
Jun 14 - Jun 15
Quality Inn Old Saybrook - Westbrook
Seasonal outdoor pool, pool umbrellas, sun loungers

Kenny's Tipperary Inn

Kenny's Tipperary Inn
2.0 star property
Culloden Shores
8.4 out of 10, Very Good, (892 reviews)
  • cleanliness
    Splash into summer with a serene outdoor pool surrounded by lush gardens and sun-soaked relaxation spaces.
The price is P7,800
P9,268 total
includes taxes & fees
May 27 - May 28
Kenny's Tipperary Inn
Seasonal outdoor pool, pool umbrellas, sun loungers

Marram

Marram
4.0 star property
Montauk
8.8 out of 10, Excellent, (254 reviews)
  • cleanliness
    Cool ocean-adjacent pool getaway with loungers, umbrellas, and beach perks for the perfect summer splash.
The price is P17,497
P32,330 total
includes taxes & fees
May 28 - May 29
Marram
Seasonal outdoor pool

The Hampton Maid

The Hampton Maid
2.5 star property
Hampton Bays
9.2 out of 10, Wonderful, (701 reviews)
  • cleanliness
    Splash into summer at this Hampton motel, where the seasonal pool and massage services await.
The price is P13,423
P15,337 total
includes taxes & fees
Jun 1 - Jun 2
The Hampton Maid
Outdoor pool, pool umbrellas, sun loungers

Offshore Spa & Residences

Offshore Spa & Residences
4.0 star property
Montauk
9.4 out of 10, Exceptional, (132 reviews)
The price is P15,558
P24,826 total
includes taxes & fees
May 25 - May 26
Offshore Spa & Residences
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

Montauk Yacht Club

Montauk Yacht Club

10/10 Excellent
"Great view!"
Nicki 1-night trip
Posted 2 days ago
Montauk Yacht Club

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. Pier Blue Inn Old Saybrook - Essex: Hotel, 5-minute walk from The Hamptons Beaches. Features 2 outdoor pools, a children's pool, and a private beach. Montauk Yacht Club: Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. The Bentley Hotel Southampton: Hotel, 5-minute walk from The Hamptons Beaches. Features free self parking, a seasonal outdoor pool, and sun loungers.
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 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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