Photo by Photo courtesy of Berkshire Visitors Bureau

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Top Pet-friendly The Berkshires Hotels

Hotel On North

297 North Street Pittsfield MA

17 min drive from Jiminy Peak Mountain Resort

Pets are welcome (fees apply) at this family-friendly hotel. Amenities like food and water bowls are sure to please four-legged travelers.

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 ...

Devonfield Inn B&B

85 Stockbridge Rd. Lee MA

43 min drive from Jiminy Peak Mountain Resort

Don't leave your four-legged friend behind. They are welcome (fees apply) at this pet-friendly bed & breakfast located near hiking and biking trails.

10/10 Exceptional! (141 reviews)

"Wonderful location and hosts are amazing. Breakfast was great. Clean."

Reviewed on Sep 14, 2026

See all 1,073 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.