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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! (801 reviews)

Wonderful stay, as usual. I have business in the Pittsfield area, 3 or 4 times a year and wouldn’t think of staying anywhere else. Quiet, comfortable….staff is always helpful and friendly….restaurant in the building is just another plus.

Reviewed on Nov 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! (763 reviews)

I love staying at the Villager Motel when I visit Williamstown. It is reasonably priced, clean, nicely upgraded and always well staffed. The only thing I would like to improve is the bed pillows. I think they were purchased new in the last 6 months, and all of the pillows are firm with no give. It ...

Reviewed on Nov 26, 2025

See all 1,088 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.