
The Berkshires Pet-friendly Vacations
Book a Pet-friendly Hotel + Flight or Car together to unlock savings
Photo by Photo courtesy of Berkshire Visitors Bureau
- Plan, book, travel with confidence
- Better togetherSave up to ₩1,660,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Pet-friendly The Berkshires Hotels

Hotel On North
297 North Street Pittsfield MA
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! (869 reviews)
"Always a great experience at Hotel on North! Great, comfortable room with amazing bathroom. Helpful and friendly staff. Safe parking in the rear secured lot."
Reviewed on Jun 24, 2026

The Villager Motel
953 Simonds Rd Williamstown MA
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! (794 reviews)
"Clean and simple accommodations. Great for a quick overnight!"
Reviewed on Jun 23, 2026

Devonfield Inn B&B
85 Stockbridge Rd. Lee MA
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
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
