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Top Pet-friendly The Berkshires Hotels

Hotel On North

297 North Street Pittsfield MA

17 min drive from Tanglewood Music Center

Four-legged friends will appreciate the amenities, such as food and water bowls, during their stay (fees apply) at this pet-friendly hotel.

9.6/10 Exceptional! (859 reviews)

"We had no expectations- so finding an impeccable hotel was a delight. We had no anticipation of beautiful bucolic views and quiet nature - so their absence didn’t matter. Had read the food was good - so that it was great was a surprise. The room size - if i had arithmetic skill and spatial awareness ..."

Reviewed on May 21, 2026

The Villager Motel

953 Simonds Rd Williamstown MA

1 hour drive from Tanglewood Music Center

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 ...

8.8/10 Excellent! (785 reviews)

"The room was comfortable and clean, I will stay there again"

Reviewed on Apr 21, 2026

Devonfield Inn B&B

85 Stockbridge Rd. Lee MA

9 min drive from Tanglewood Music Center

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! (138 reviews)

"Excellent food and helpful staff"

Reviewed on May 13, 2026

See all 1,125 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.