
The Berkshires Pet-friendly Holidays
Book a 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 NZ$2,400 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
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! (866 reviews)
"The whole experience was great. Staff excellent."
Reviewed on 16 June 2026

The Villager Motel
953 Simonds Rd Williamstown MA
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! (792 reviews)
"Very clean and quiet place . Bed was so comfortable"
Reviewed on 16 June 2026

Devonfield Inn B&B
85 Stockbridge Rd. Lee MA
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! (138 reviews)
"Excellent food and helpful staff"
Reviewed on 13 May 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.
