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

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Check availability on Hillsdale Hotels with a Pool

Tonight
May 3 - May 4
Tomorrow
May 4 - May 5
Next weekend
May 8 - May 10
In two weeks
May 15 - May 17

Our top choices for Hillsdale hotels with a pool

Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, sun loungers

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
The price is CA $141
CA $157 total
includes taxes & fees
May 7 - May 8
The Yankee Inn
Indoor pool

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (922 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
The price is CA $119
CA $164 total
includes taxes & fees
May 24 - May 25
Berkshire Mountain Lodge
Indoor pool

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (758 reviews)
  • cleanliness
    Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
The price is CA $162
CA $181 total
includes taxes & fees
May 18 - May 19
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (558 reviews)
  • cleanliness
    Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
The price is CA $149
CA $167 total
includes taxes & fees
May 5 - May 6
The Little Lion
Exterior

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.
The price is CA $107
CA $120 total
includes taxes & fees
May 4 - May 5
Howard Johnson by Wyndham Lenox
Property grounds

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,002 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
The price is CA $196
CA $279 total
includes taxes & fees
May 26 - May 27
The Red Lion Inn
Indoor pool

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 price is CA $242
CA $270 total
includes taxes & fees
May 10 - May 11
Element Lenox Berkshires
Seasonal outdoor pool

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.
The price is CA $207
CA $231 total
includes taxes & fees
May 4 - May 5
Little Cat Lodge
Outdoor dining

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.
The price is CA $202
CA $386 total
includes taxes & fees
May 4 - May 5
Private Yacht on Catskill Creek
Seasonal outdoor pool

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (854 reviews)
  • cleanliness
    Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.
The price is CA $109
CA $121 total
includes taxes & fees
May 4 - May 5
Berkshire Inn
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 Hillsdale

Breakfast included
4 stars

Top Hillsdale Hotel Reviews

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Clean. Friendly staff."
Charlene 2-night trip
Posted 3 hours ago
Quality Inn Great Barrington

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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