The Berkshires Pet-friendly Holidays
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 together
Save up to ₹43,962 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top Pet-friendly The Berkshires Hotels
Stay Berkshires
1146 Cold Spring Road, Williamstown, MA
Stay at this hotel in Williamstown. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Margaret Lindley Park and Lindley Park are located ...
8.2/10 Very Good! (353 reviews)
"Nice option to stay near MASS MOCA."
Reviewed on 4 Dec 2024
Hotel On North
297 North Street, Pittsfield, MA
Stay at this 3.5-star business-friendly hotel in Pittsfield. Enjoy free Wi-Fi, free parking and room service. Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (742 reviews)
"The Hotel is lovely, clean, and has a minimal but thoughtful aesthetic. The bathroom and bedroom are huge, and the restaurant connected to the hotel is charming. The only drawback is the location. The town center is dilapidated and rundown, with many closed storefronts. I hope the town of Pittsfield ..."
Reviewed on 28 Jun 2025
The Villager Motel
953 Simonds Rd, Rt 7 North, 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 ...
8.6/10 Excellent! (717 reviews)
Nice clean room!
"As many of the reviewers have said, the place was comfortable and clean! I loved the fact that I could park my car directly in front of the motel. Bed was comfortable & there was a nice table and chair with a light. I felt safe with Motel and the surroundings. I would definitely recommend this place, ..."
Reviewed on 30 Jun 2025
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.