The Berkshires Adventure Holidays 2026

Photo by Photo courtesy of Berkshire Visitors Bureau

Plan, book, travel with confidence
Better together
Save up to NZ$2,400 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 Adventure The Berkshires Hotels

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

35 min drive from Tanglewood Music Center

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

8.8/10 Excellent! (2,533 reviews)

"Large, clean rooms and friendly staff. The location is really nice - tucked into the woods a short drive away from tourist sites. Lots of kids and families, but still private. Only downside was that the rooms aren't soundproofed, so you can hear people moving overhead. But everyone was respectful ..."

Reviewed on 14 Aug 2026

Hampton Inn & Suites Berkshires-Lenox

445 Pittsfield Rd Lenox MA

8 min drive from Tanglewood Music Center

Stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their ...

9.2/10 Wonderful! (1,001 reviews)

"Everything was so clean and efficient."

Reviewed on 12 Aug 2026

Berkshire Valley Inn

2541 Hancock Rd Williamstown MA

42 min drive from Tanglewood Music Center

Stay at this hotel in Williamstown. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms in their reviews. ...

9.2/10 Wonderful! (577 reviews)

"We LOVED our stay! Pamela has done a beautiful job paying attention to the details. We will definitely be back. Highly recommend!"

Reviewed on 10 Aug 2026

See all 1,088 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.