Photo by Photo courtesy of Berkshire Visitors Bureau

Plan, book, travel with confidence
Better together
Save up to CA $4,200 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

Cheap Hotels in The Berkshires

Monument Mountain Motel

247 Stockbridge Rd Great Barrington MA

25 min drive from Tanglewood Music Center

Stay at this motel in Great Barrington. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...

9/10 Wonderful! (851 reviews)

Good

Reviewed on May 11, 2026

Quality Inn Great Barrington

372 Main Street Great Barrington MA

27 min drive from Tanglewood Music Center

Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...

8.4/10 Very Good! (1,013 reviews)

really enjoyed my stay here. The staff are friendly and helpful, the rooms are very clean and well put together, the bed was comfortable, and conveniently, there's a CVS right in the hotel parking lot, which is great if you, like me, forgot to pack something or needed something more than what the ...

Reviewed on May 11, 2026

The Yankee Inn

461 Pittsfield Rd Lenox MA

8 min drive from Tanglewood Music Center

Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...

9.2/10 Wonderful! (1,006 reviews)

My partner and I just moved back to MA so we are local to the area. We have stayed there just to have an evening of respite together and solo and send our family there during holidaze! Very friendly staff, comfortable rooms, prime location, and breezy breakfast options.

Reviewed on May 8, 2026

See all 1,124 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.