Photo by Photo courtesy of Berkshire Visitors Bureau

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Top Romantic The Berkshires Hotels

Shaker Mill Inn

2 Oak Street West Stockbridge MA

25 min walk from Tanglewood Music Center

Stay at this B&B in West Stockbridge. Enjoy free parking and daily housekeeping. Popular attractions Tanglewood Music Center and Ebenezer II Gifts and Antiques ...

9.6/10 Exceptional! (461 reviews)

"Really clean, comfortable, and quiet. The pastries and fruit they provided were delicious too !"

Reviewed on 9 June 2026

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

35 min drive from Tanglewood Music Center

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

8.8/10 Excellent! (2,396 reviews)

"I enjoy staying here . The front desk staff was very friendly . I like the hours of outdoor and indoor pool . My only complaints is the rooms are very very outdated and had to go to front desk every day because keys didnt work ."

Reviewed on 15 June 2026

Holiday Inn & Suites Pittsfield-Berkshires by IHG

One West Street Pittsfield MA

16 min drive from Tanglewood Music Center

Stay at this business-friendly hotel in Pittsfield. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean ...

8/10 Very Good! (1,009 reviews)

"Undergoing a major renovation"

Reviewed on 14 June 2026

See all 1,102 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.