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

56 min drive from Tanglewood Music Center

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 ...

Hotel On North

297 North Street Pittsfield MA

17 min drive from Tanglewood Music Center

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! (837 reviews)

The hotel was even more beautiful in person! Rooms were incredibly spacious and lovely. The staff was incredibly friendly and helpful. Great stay would definitley return.

Reviewed on 16 Mar 2026

The Villager Motel

953 Simonds Rd Williamstown MA

1 hour drive from Tanglewood Music Center

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! (783 reviews)

No chance of beating the price for the overall stay. I saved about 400.00 over two nights by staying there instead of a major hotel downtown. Plus, it’s not too bad of a ride to get downtown for other food options outside of the ones right next to the motel. Friendly staff, good experience, solid ...

Reviewed on 24 Mar 2026

See all 1,118 properties in The Berkshires

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.