The Berkshires Kid friendly Vacations 2026

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

13 min walk from Jiminy Peak Mountain Resort

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

8.8/10 Excellent! (2,756 reviews)

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

Travelers say...

"This was our 10 yr celebrating my girlfriend’s birthday at Vacation Village. It’s always a nice escape in the fall season. We usually get the larger “A” rooms as we want the in room jacuzzi. This time I got the same larger room but it was a “C” unit. It was a bit smaller all around. And the bed was ..."

Reviewed on Oct 18, 2026

Hotel Downstreet, an Ascend Collection Hotel

40 Main St North Adams MA

25 min drive from Jiminy Peak Mountain Resort

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 ...

9/10 Wonderful! (1,003 reviews)

"Would stay here again for sure"

Reviewed on Oct 18, 2026

Williamstown Motel

295 Main Street Williamstown MA

25 min drive from Jiminy Peak Mountain Resort

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 1,097 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.