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 breakfast, free parking, and daily housekeeping. Popular attractions Tanglewood Music Center and Ebenezer II ...

9.6/10 Exceptional! (398 reviews)

"I enjoyed my stay in The Clark Suite. Very easy check in and helpful staff. West Stockbridge is a quaint town, easy to walk about and wonderful dinner/ice cream options. The Shaker Inn provided Gluten Free options for breakfast including fresh oj, fruit and great coffee. The room/bathroom were immaculate. ..."

Reviewed on Sep 22, 2025

Vacation Village in the Berkshires

276 Brodie Mountain Rd, Williamstown, MA

35 min drive from Tanglewood Music Center

A garden and in-room fireplaces await at this romantic condo, which also offers a terrace and an outdoor pool.

8.6/10 Excellent! (2,026 reviews)

"Clean room and friendly staff. No issues at all. Will definitely stay again."

Reviewed on Sep 29, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG

One West Street, Pittsfield, MA

16 min drive from Tanglewood Music Center

A garden and onsite dining await at this romantic hotel, which also offers a terrace and a bar.

7.8/10 Good! (881 reviews)

Couples like: onsite spa services, bar, winery tours

Travelers say...

"It has been more than 10 years since parking garage available"

Reviewed on Sep 23, 2025

See all 1,120 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.