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

Stay at this hotel in Williamstown. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Margaret Lindley Park and Lindley Park are located ...

8.2/10 Very Good! (353 reviews)

Nice option to stay near MASS MOCA.

Reviewed on 4 Dec 2024

Hotel On North

297 North Street Pittsfield MA

17 min drive from Jiminy Peak Mountain Resort

Stay at this business-friendly hotel in Pittsfield. Enjoy free Wi-Fi, free parking and room service. Our guests praise the helpful staff and the clean rooms ...

9.4/10 Exceptional! (805 reviews)

Spacious rooms. Attentive staff. Free parking behind the hotel.

Reviewed on 5 Dec 2025

The Villager Motel

953 Simonds Rd Williamstown MA

31 min drive from Jiminy Peak Mountain Resort

Stay at this business-friendly motel in Williamstown. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...

8.6/10 Excellent! (764 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 26 Nov 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.