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! (446 reviews)

Spacious, clean, nice breakfast

Reviewed on Feb 15, 2026

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.

8.8/10 Excellent! (2,305 reviews)

Hot tub and pool both clean and well maintained

Reviewed on Mar 15, 2026

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.

8/10 Very Good! (1,002 reviews)

Couples like: onsite spa services, bar, winery tours

Travelers say...

yes

Reviewed on Mar 16, 2026

See all 1,113 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.