Find Hotels with a Pool in Hillsdale, NY

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Check availability on Hillsdale Hotels with a Pool

Our top choices for Hillsdale hotels with a pool

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (23 reviews)
  • cleanliness
    Modern comforts and year-round indoor pool await at Element Lenox Berkshires near Tanglewood.
The price is AED 511
AED 570 total
includes taxes & fees
26 Mar - 27 Mar
Element Lenox Berkshires

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
The price is AED 340
AED 380 total
includes taxes & fees
22 Mar - 23 Mar
The Yankee, Trademark Collection by Wyndham

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (872 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
The price is AED 391
AED 518 total
includes taxes & fees
1 Apr - 2 Apr
Berkshire Mountain Lodge

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (839 reviews)
  • cleanliness
    Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
The price is AED 290
AED 324 total
includes taxes & fees
15 Mar - 16 Mar
Howard Johnson by Wyndham Lenox

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, (744 reviews)
  • cleanliness
    Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
The price is AED 393
AED 439 total
includes taxes & fees
16 Mar - 17 Mar
Holiday Inn Express Hotel & Suites Great Barrington by IHG

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (554 reviews)
  • cleanliness
    Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
The price is AED 404
AED 451 total
includes taxes & fees
15 Mar - 16 Mar
The Little Lion

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
The price is AED 498
AED 720 total
includes taxes & fees
7 Apr - 8 Apr
The Red Lion Inn

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
The price is AED 408
AED 456 total
includes taxes & fees
22 Mar - 23 Mar
Hampton Inn & Suites Berkshires-Lenox

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.8 out of 10, Exceptional, (21 reviews)
  • cleanliness
    Berkshire mountain retreat features outdoor pool, sauna, and complimentary bicycles.
The price is AED 867
AED 1,091 total
includes taxes & fees
15 Mar - 16 Mar
Prospect Berkshires

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (170 reviews)
  • cleanliness
    Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
The price is AED 509
AED 585 total
includes taxes & fees
14 Apr - 15 Apr
Blackberry River 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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Frequently asked questions

What are some accommodations with pools in Hillsdale?
The Brooks Motel: Offers free self parking, an indoor pool, and complimentary wireless internet access. Berkshire Mountain Lodge: Features 2 indoor pools, 2 outdoor pools, and a snack bar/deli. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy: Features a health club, an indoor pool, and complimentary wired internet access. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG: Offers a seasonal outdoor pool, an indoor pool, and buffet. Berkshires Untold: Features 3 restaurants, an outdoor pool, and spa services.
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.