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! (821 reviews)

Great staff, beautiful hotel. Would definitely recommend

Reviewed on 27 Jan 2026

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! (772 reviews)

Excellent simple motel. The room was immaculately clean and relatively recently updated. I felt very comfortable there and would stay again. The shower and bedding were in great shape. The breakfast is cereal and grocery store bagels (not much, but its free...).

Reviewed on 2 Feb 2026

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.