Photo by Photo courtesy of Berkshire Visitors Bureau
Find Hotels with a Pool in The Berkshires, MA
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Our top choices for The Berkshires hotels with a pool
8.8 out of 10, Excellent, (2182)
"Awesome for ski"
Lazar
The price is ₩153,846
₩188,078 total
includes taxes & fees
Jan 7 - Jan 8, 2026
9.2 out of 10, Wonderful, (1006)
"Friendly staff, very clean room and super comfy bed"
Linda
The price is ₩124,548
₩139,121 total
includes taxes & fees
Jan 5 - Jan 6, 2026
8.8 out of 10, Excellent, (1002)
"Old time charm and hot tub under the stars"
Lori
The price is ₩221,954
₩314,035 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHGSouth Lee
9.0 out of 10, Wonderful, (806)
"Convenient location, very roomy, well equipped kitchen.
"
Carolyn
The price is ₩189,153
₩240,218 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
8.0 out of 10, Very Good, (997)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
Frank
The price is ₩145,010
₩161,982 total
includes taxes & fees
Jan 9 - Jan 10, 2026
9.0 out of 10, Wonderful, (795)
"Spacious room and loved pool and hot tub!"
Deanna
The price is ₩146,023
₩196,163 total
includes taxes & fees
Jan 14 - Jan 15, 2026
9.6 out of 10, Exceptional, (14)
"Rooms were very clean and spacious."
Morgan
The price is ₩199,758
₩223,129 total
includes taxes & fees
Jan 7 - Jan 8, 2026
9.2 out of 10, Wonderful, (592)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
Mingming
The price is ₩205,677
₩229,742 total
includes taxes & fees
Jan 20 - Jan 21, 2026
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.
Top The Berkshires Hotel Reviews
The Yankee, Trademark Collection by Wyndham
10/10 Excellent
