A rural landscape with snow-covered fields, a winding road, and scattered trees.

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

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, (1,010 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
The price is NT$4,845
NT$5,412 total
includes taxes & fees
Jul 12 - Jul 13
The Yankee Inn
Indoor pool

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (127 reviews)
  • cleanliness
    Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
The price is NT$5,047
NT$5,638 total
includes taxes & fees
Jul 16 - Jul 17
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (580 reviews)
  • cleanliness
    Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
The price is NT$3,589
NT$4,009 total
includes taxes & fees
Jul 14 - Jul 15
The Little Lion
Seasonal outdoor pool

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (421 reviews)
  • cleanliness
    Splash into a seasonal outdoor pool near Tanglewood Music Center, offering a sunny retreat in a peaceful location.
The price is NT$3,525
NT$3,937 total
includes taxes & fees
Jul 13 - Jul 14
Sunset Inn
Outdoor pool

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (486 reviews)
  • cleanliness
    Splash into sunny days at this motel's refreshing outdoor pool, complete with terrace views and garden surroundings.
The price is NT$2,163
NT$2,422 total
includes taxes & fees
Jul 12 - Jul 13
Berkshire Travel Lodge
Exterior

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,009 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
The price is NT$5,640
NT$7,731 total
includes taxes & fees
Jul 22 - Jul 23
The Red Lion Inn
M3 Romantic Suite | Living area | 43-inch LCD TV with digital channels, streaming services

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (191 reviews)
  • cleanliness
    Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
The price is NT$4,989
NT$5,738 total
includes taxes & fees
Jul 12 - Jul 13
Blackberry River Inn
Exterior

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (881 reviews)
  • cleanliness
    Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
The price is NT$3,172
NT$3,544 total
includes taxes & fees
Jul 12 - Jul 13
Howard Johnson by Wyndham Lenox
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, (785 reviews)
  • cleanliness
    Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
The price is NT$4,934
NT$5,512 total
includes taxes & fees
Jul 26 - Jul 27
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Seasonal outdoor pool

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (875 reviews)
  • cleanliness
    Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.
The price is NT$2,884
NT$3,221 total
includes taxes & fees
Jul 19 - Jul 20
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

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

8/10 Good
"Room was a good size.Front desk associate when we arrived helped with suggestions for dinner. In the morning another front desk associate helped to replenish the coffee when I let them know it was empty."
Debra 1-night trip
Posted 1 hour ago
Hampton Inn & Suites Berkshires-Lenox

Frequently asked questions

What are some accommodations with pools in Hillsdale?
The Yankee Inn: Offers a seasonal outdoor pool, an indoor pool, and buffet. Berkshire Mountain Lodge: Provides free self parking, an indoor pool, and complimentary wireless internet access. Berkshires Untold: Offers 3 restaurants, an outdoor pool, and spa services. The Red Lion Inn: Offers buffet, an indoor pool, and complimentary wired internet access. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy: Features 2 indoor pools, 2 outdoor pools, and a snack bar/deli.
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.