Find Hotels with a Pool in Hillsdale, NY from CA $120

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Our top choices for Hillsdale hotels with a pool

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,003 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
"Helpful and friendly staff, clean room, great pool amd jaccuzzi."
United States
Zina
The price is CA $141
CA $157 total
includes taxes & fees
May 6 - May 7
The Yankee Inn

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (559 reviews)
  • cleanliness
    Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
"A nice little motel close to Catamount ski resort!"
United States
Benjamin
The price is CA $149
CA $167 total
includes taxes & fees
May 6 - May 7
The Little Lion

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (853 reviews)
  • cleanliness
    Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
"Plenty of parking and nice pool."
United States
Dan
The price is CA $107
CA $120 total
includes taxes & fees
May 6 - May 7
Howard Johnson by Wyndham Lenox

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (923 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
"Spacious, clean, and the pool was warm and perfect for family swimming"
United States
Danielle
The price is CA $119
CA $164 total
includes taxes & fees
May 24 - May 25
Berkshire Mountain Lodge

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (77 reviews)
  • cleanliness
    Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.
"We look forward to returning and using the pool."
United States
Evelyn
The price is CA $207
CA $231 total
includes taxes & fees
May 11 - May 12
Little Cat Lodge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (25 reviews)
  • cleanliness
    Modern comforts and year-round indoor pool await at Element Lenox Berkshires near Tanglewood.
"The room we stayed in was extremely clean and comfy. The whole hotel was very nice and had an awesome breakfast. Will be staying here again for sure. "
United States
Keith
The price is CA $242
CA $270 total
includes taxes & fees
May 11 - May 12
Element Lenox Berkshires

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,004 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
"The pool and hot tube were open, maybe bring a swimsuit if you are up for a soak in the hot tub on a cold snowy day or night."
United States
Judith Pauline
The price is CA $200
CA $284 total
includes taxes & fees
May 18 - May 19
The Red Lion Inn

Private Yacht on Catskill Creek

Private Yacht on Catskill Creek
Catskill
9.8 out of 10, Exceptional, (28 reviews)
  • cleanliness
    Aquatic adventures await at this waterfront houseboat with outdoor pool and water park on serene Catskill Creek.
"what a fabulous getaway idea! to be right on the water - fishing, kayaking, eating, drinking... there is a nice restaurant/bar with a patio overlooking the water that was very nice and convenient as well as the showers and the pool. We trailered our motorcycles with us and were able to enjoy ourselves immensely"
United States
Jeanette G.
The price is CA $202
CA $387 total
includes taxes & fees
May 6 - May 7
Private Yacht on Catskill Creek

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,006 reviews)
  • cleanliness
    Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
"Nice pool and gym facility."
United States
Melanie
The price is CA $173
CA $193 total
includes taxes & fees
May 25 - May 26
Hampton Inn & Suites Berkshires-Lenox
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 Hillsdale

Top Hillsdale Hotel Reviews

Frequently asked questions

What are some accommodations with pools in Hillsdale?
Berkshire Mountain Lodge: Features free self parking, an indoor pool, and complimentary wireless internet access. Berkshires Untold: Hotel, 15-minute walk from National Shrine of the Divine Mercy. Features 3 restaurants, an outdoor pool, and spa services. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy: Hotel located near National Shrine of the Divine Mercy. Offers 2 indoor pools, 2 outdoor pools, and a snack bar/deli. The Red Lion Inn: Features buffet, an indoor pool, and complimentary wired internet access. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG: Features a sauna, an indoor pool, and free self parking.
What is there to see and do in Hillsdale?
Spend some time experiencing the great outdoors at Copake Lake and Mosquito Island. Discover sights such as Catamount Aerial Adventure Park, Catamount Ski Area, and Hillsdale Town Hall during your stay.
When is the best time to book a hotel with a pool in Hillsdale?
Taking into account the local weather in Hillsdale can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 68°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Hillsdale are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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