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 2024/12/4

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! (814 reviews)

Very clean hotel. Staff was so friendly and helpful. Location is perfect and own parking lot was great.

Reviewed on 2026/1/11

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 2025/12/16

See all 1,068 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.