Photo by Photo courtesy of Berkshire Visitors Bureau

Plan, book, travel with confidence
Better together
Save up to ₩1,660,000 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! (2,388 reviews)

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

Travelers say...

"While traveling in the area for summer we found Vacation Village. Great jump off point, great amenities, helpful staff, nice set up inside the condo, pots, pans, utensils, glassware, other cooking utensils in good shape. Private decks are a nice touch. Best bargain in the area by far!!! Will be ..."

Reviewed on Jun 1, 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 breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...

8.8/10 Excellent! (1,003 reviews)

"Check in was simple and quick. Staff was courteous and helpful. The room was clean and spacious. We had a pleasant stay and checkout was simple."

Reviewed on Jun 1, 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! (321 reviews)

"Absolutely lovely. Clean! New carpet. Fridge and microwave. Comfy bed. Ground floor only and park right in front of the door-a must for those with physical issues. Great owner! Just a great visit. Will be gifting my son md his wife a trip to the area with williamstown Motel to stay."

Reviewed on May 29, 2026

See all 1,101 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.