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.

8.2/10 Very Good! (353 reviews)

Nice option to stay near MASS MOCA.

Reviewed on Dec 4, 2024

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.

9.4/10 Exceptional! (809 reviews)

Staff is incredibly helpful and friendly

Reviewed on Dec 22, 2025

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 ...

8.6/10 Excellent! (768 reviews)

Everything was perfect

Reviewed on Dec 16, 2025

See all 1,084 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.