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 Tanglewood Music Center

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 ...

9.6/10 Exceptional! (846 reviews)

My wife and I both enjoyed our stay. The decor and atmosphere are very nice. The room was spacious. And the facilities were fun—I enjoyed the sitting area on the second floor with all the books, games, and puzzles.

Reviewed on 27 Apr 2026

The Villager Motel

953 Simonds Rd Williamstown MA

1 hour drive from Tanglewood Music Center

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 ...

8.8/10 Excellent! (785 reviews)

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

Reviewed on 21 Apr 2026

Devonfield Inn B&B

85 Stockbridge Rd. Lee MA

9 min drive from Tanglewood Music Center

Stay at this golf B&B in Lee. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions National Shrine of the Divine Mercy and Tanglewood Music ...

10/10 Exceptional! (137 reviews)

Had a wonderful stay. The property is charming, elegant, and beautifully maintained, with a peaceful Berkshires setting. Our hosts were warm, welcoming, and made us feel right at home from the moment we arrived. Everything from the comfortable room to the thoughtful touches throughout our stay exceeded ...

Reviewed on 22 Mar 2026

See all 1,122 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.