The Berkshires Pet-friendly Vacations
Book a Pet-friendly Hotel + Flight or Car together to unlock savings
- 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
- 17 min drive from Tanglewood Music Center
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! (886 reviews)
"I have never complained about a hotel before however, Soto was quite overpriced for what it was. The young female bartender was extremely inhospitable and rude to my friend and to another couple. She actually sneered l. The front desk woman seemed utterly harassed when we checked in—no smiles, no ..."
Reviewed on Aug 4, 2026
The Villager Motel
953 Simonds Rd Williamstown MA
- 1 hour drive from Tanglewood Music Center
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 ...
Devonfield Inn B&B
85 Stockbridge Rd. Lee MA
- 9 min drive from Tanglewood Music Center
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! (140 reviews)
"The owners are so nice!!! Tha property is beautiful and the people that play the piano and sing during the day is the most relaxing and incredible experience!!!!"
Reviewed on Aug 4, 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.
