Photo by Photo courtesy of Berkshire Visitors Bureau

Plan, book, travel with confidence
Better together
Save up to ₩234,741 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! (2,335 reviews)

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

Travelers say...

While this is a good value for the money for a one bedroom with separate kitchenette and living area, this is basically 2nd or 3rd rate for a timeshare unit. Couch is uncomfortable to sit on and bed isn't the best. Didn't provide some very basics, such as dish soap to wash dishes and pans which are ...

Reviewed on Apr 18, 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! (1,001 reviews)

Nice staff comfy bed nice views

Reviewed on Apr 8, 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 ...

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.