Photo by Photo courtesy of Berkshire Visitors Bureau

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Top Pet-friendly The Berkshires Hotels

Stay Berkshires

1146 Cold Spring Road Williamstown MA

22 min drive from Jiminy Peak Mountain Resort

Your four-legged friend can come along to this pet-friendly hotel (fees apply for pets). If you need a walk, try nearby Margaret Lindley Park.

Hotel On North

297 North Street Pittsfield MA

17 min drive from Jiminy Peak Mountain Resort

Four-legged friends will appreciate the amenities, such as food and water bowls, during their stay (fees apply) at this pet-friendly hotel.

9.6/10 Exceptional! (825 reviews)

Room was spotless, staff was amazing! Loved the bathroom setup! Will recommend and stay again!

Reviewed on Feb 9, 2026

The Villager Motel

953 Simonds Rd Williamstown MA

31 min drive from Jiminy Peak Mountain Resort

Book a stay at this business-friendly motel in Williamstown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...

8.8/10 Excellent! (779 reviews)

very clean, up to day, no thrills overnighter. perfect stop from NYC to VT skiing

Reviewed on Feb 20, 2026

See all 1,100 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.