Photo by Photo courtesy of Berkshire Visitors Bureau

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Pet-friendly Hotels in The Berkshires

Berkshires Untold

194 Pittsfield Rd Lenox MA

28 min drive from Jiminy Peak Mountain Resort

Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...

9/10 Wonderful! (854 reviews)

loved

Reviewed on Feb 2, 2026

The Williams Inn

101 Spring Street Williamstown MA

26 min drive from Jiminy Peak Mountain Resort

Book a stay at this business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our ...

9.6/10 Exceptional! (572 reviews)

Clean

Reviewed on Jan 31, 2026

Holiday Inn & Suites Pittsfield-Berkshires by IHG

One West Street Pittsfield MA

18 min drive from Jiminy Peak Mountain Resort

Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...

8/10 Very Good! (1,001 reviews)

Rooms were clean and spacious. Our room had 2 queen beds and they easily accommodated 2 of us and our late teen children. It's only 20 minutes from Jiminy Peak skiing area. There are several breakfast and food places nearby.

Reviewed on Feb 2, 2026

See all 1,089 properties in The Berkshires

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.