The Berkshires Pet-friendly Vacations 2026

Photo by Photo courtesy of Berkshire Visitors Bureau

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Top Pet-friendly The Berkshires Hotels

Berkshires Untold

194 Pittsfield Rd Lenox MA

28 min drive from Jiminy Peak Mountain Resort

Dogs and cats may join you (for a fee) during your stay at this pet-friendly lodge. Take the opportunity to stretch your legs on the nearby hiking or biking ...

The Black Swan Lee - Lenox, an Ascend Collection Hotel

435 Laurel St Lee MA

39 min drive from Jiminy Peak Mountain Resort

Make it a pet-friendly trip and bring along your four-legged friend. Dogs are welcome (fees apply) at this waterfront hotel.

9.2/10 Wonderful! (1,010 reviews)

"Property is on a little lake and we had a balcony room with view of the lake. I can imagine it must be great to have in the warmer months, but we enjoyed the view nonetheless. Everything was clean, staff was friendly, the restaurant food we sampled was very good, the jet tub was much appreciated, ..."

Reviewed on Oct 24, 2026

The Red Lion Inn

30 Main Street Stockbridge MA

46 min drive from Jiminy Peak Mountain Resort

Four-legged friends are welcome (fees apply) at this historic hotel offering pet-friendly amenities, like food and water bowls. While you're here, explore the ...

See all 1,090 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.