Hotels with Swimming Pools in Shelter Island

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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, (311 reviews)
  • cleanliness
    Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
"The pool was great"
United States
Michelle
The price is S$129
includes taxes & fees
27 May - 28 May
Clinton Motel

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 pool area was amazing"
United States
Elissa
The price is S$182
includes taxes & fees
27 May - 28 May
Breakers Montauk

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 rooms were clean it a walk to town the pool area is great I will definitely book this hotel again"
United States
Jennifer
The price is S$212
includes taxes & fees
25 May - 26 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, (474 reviews)
  • cleanliness
    Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodation.
"Pool was open and, while small, it was clean and refreshing. The woman at the front desk was very kind and helpful - made me feel welcome. The property itself is a bit outdated but it looks like they are working to update it. the room was very clean and comfortable for our family of 3. Only issue was the AC system was VERY loud and woke me up every 20 minutes when it went off. I had to shut it off around 3 am and try to salvage my nights sleep. Not sure if this is all rooms or just bad luck on...
United States
Melissa
The price is S$119
includes taxes & fees
26 May - 27 May
Econo Lodge Inn & Suites Old Saybrook Westbrook

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.
"Pool is nice!"
United States
Cassidy
The price is S$183
includes taxes & fees
25 May - 26 May
Aqualina Inn Montauk

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 pool was so relaxing"
United States
Kathleen
The price is S$174
includes taxes & fees
21 Jun - 22 Jun
Quality Inn Old Saybrook - Westbrook

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.
"Great pool and patio area to gather with friends."
United States
barbara
The price is S$192
includes taxes & fees
26 May - 27 May
Kenny's Tipperary Inn

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.
"Having the the beach and a heated pool was terrific as was the room."
United States
Allan
The price is S$606
includes taxes & fees
31 May - 1 Jun
Marram

The Hampton Maid

The Hampton Maid
2.5 star property
Hampton Bays
9.2 out of 10, Wonderful, (700 reviews)
  • cleanliness
    Splash into summer at this Hampton motel, where the seasonal pool and massage services await.
"We left how cute and quaint the grounds were and had a beautiful pool and grass area with a playground."
United States
Mary
The price is S$319
includes taxes & fees
26 May - 27 May
The Hampton Maid

Offshore Spa & Residences

Offshore Spa & Residences
4.0 star property
Montauk
9.4 out of 10, Exceptional, (132 reviews)
"Great facilities with gym, sauna, cold plunge, pool."
United States
Sera
The price is S$514
includes taxes & fees
25 May - 26 May
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.

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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