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

8.6/10 Excellent! (1,928 reviews)

"Nice and quiet also clean."

Reviewed on Aug 4, 2025

Hampton Inn & Suites Berkshires-Lenox

445 Pittsfield Rd, Lenox, MA

8 min drive from Tanglewood Music Center

Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...

9/10 Wonderful! (1,003 reviews)

"Hi, when I checked in the guy at the front desk said that the hotel was full so they gave me a different type of room. I told him I paid for a two queen bed and somehow he found me a room. So basically he lied. Terrible terrible impression."

Reviewed on Jul 19, 2025

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 WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...

9/10 Wonderful! (554 reviews)

Reviewed on Jul 29, 2025

See all 1,107 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.