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! (387 reviews)

"The hospitality and attentiveness was outstanding. Both John and his wife Patti were there for any needs we had. I had by accident via Expedia set my arrival date for a day later than we arrived. When we got to Shaker I discovered this. John accommodated us nevertheless. The grounds were great and ..."

Reviewed on Jul 12, 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! (1,888 reviews)

"The room was massive and had all kitchen needs met"

Reviewed on Jul 18, 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! (825 reviews)

Couples like: onsite spa services, bar, winery tours

Very solid spot

"Great spot for exploring the area. Walking distance to downtown, and easy drive to nature, which is why I was in town w/ friends. Only complaint is that the hot water ran out really fast in the showers the days we were there"

Reviewed on Jul 16, 2025

See all 1,114 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.