Photo by Photo courtesy of Berkshire Visitors Bureau

Plan, book, travel with confidence
Better together
Save up to ￥109,000 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 Kid friendly The Berkshires Hotels

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

35 min drive from Tanglewood Music Center

Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...

8.8/10 Excellent! (2,365 reviews)

Families like: Kids pool, playground, game room, skiing nearby

Travelers say...

"The rooms were very clean. Kodos to the housekeeping department. The checking in was a bit of a issue. We asked for a apartment that had no stairs as my wife has a problem with stairs but instead we we given a 3rd storie walkup. The picture of the bathroom is very decieving. The advertized pictures ..."

Reviewed on May 24, 2026

Hotel Downstreet, an Ascend Collection Hotel

40 Main St North Adams MA

58 min drive from Tanglewood Music Center

Book a stay at this business-friendly hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff ...

8.8/10 Excellent! (1,003 reviews)

"I loved the use of space for local artists to display there art. Beautiful work. The hotel was very clean. Loved that you could get a coffee or water throughout the day. I wish that the pool was opened all day. Ample parking"

Reviewed on May 23, 2026

Williamstown Motel

295 Main Street Williamstown MA

58 min 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 ...

9.2/10 Wonderful! (320 reviews)

"The room was very clean and comfortable, a great value. The owners were available and very helpful and welcoming. You’ll be pleasantly surprised at what you can get at this price point."

Reviewed on May 20, 2026

See all 1,125 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.