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Find Hotels with a Pool in The Berkshires, MA

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Our top choices for The Berkshires hotels with a pool

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2182)
"Awesome for ski"
United States
Lazar
The price is ₩153,846
₩188,078 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Vacation Village in the Berkshires

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1006)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is ₩124,548
₩139,121 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Yankee, Trademark Collection by Wyndham

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1002)
"Old time charm and hot tub under the stars"
United States
Lori
The price is ₩221,954
₩314,035 total
includes taxes & fees
Jan 14 - Jan 15, 2026
The Red Lion Inn

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 IHG
3.5 star property
South Lee
9.0 out of 10, Wonderful, (806)
"Convenient location, very roomy, well equipped kitchen. "
United States
Carolyn
The price is ₩189,153
₩240,218 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (997)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is ₩145,010
₩161,982 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (795)
"Spacious room and loved pool and hot tub!"
United States
Deanna
The price is ₩146,023
₩196,163 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Berkshire Mountain Lodge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (14)
"Rooms were very clean and spacious."
United States
Morgan
The price is ₩199,758
₩223,129 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Element Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (592)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
The price is ₩205,677
₩229,742 total
includes taxes & fees
Jan 20 - Jan 21, 2026
Courtyard by Marriott Lenox Berkshires

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, (710)
"Great hospitality "
United States
regina maria
The price is ₩158,327
₩176,852 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (659)
"The room was very clean with comfortable King bed. We really enjoyed the hot tub."
United States
Christine
The price is ₩189,223
₩211,361 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Hilton Garden Inn Lenox Pittsfield
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