Top Pet-friendly The Berkshires Hotels

The Williams Inn

101 Spring Street Williamstown MA

26 min drive from Jiminy Peak Mountain Resort

This hotel is pet-friendly, allowing dogs with an additional fee. If you're going for a walk during your stay, swing by nearby Linear Park.

9.6/10 Exceptional! (546 reviews)

Good room size, staff was wonderful. Location is prime.

Reviewed on Nov 29, 2025

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.

9/10 Wonderful! (1,005 reviews)

Love this place! Great rooms, view of the lake, Indian restaurant inside, and wonderful breakfast choices. We’ll be back.

Reviewed on Nov 24, 2025

The Red Lion Inn

30 Main Street Stockbridge MA

46 min drive from Jiminy Peak Mountain Resort

You're welcome to bring along four-legged friends (fees apply) at this historic hotel. During your pet-friendly getaway, why not explore the nearby hiking or ...

8.8/10 Excellent! (1,003 reviews)

Quaint Inn located in the Berkshire. Dinner in the tavern was delish. The main inn lobby has plenty of seating to lounge around and people watch. We enjoyed our stay.

Reviewed on Nov 20, 2025

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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.