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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! (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 2025/11/22

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 2025/11/26

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.