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! (392 reviews)

"Very casual and easy check in and out; lovely and substantial breakfast"

Reviewed on 11 Aug. 2025

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! (1,959 reviews)

"The property was nice and had activities like a volley ball net and basketball court however no balls were provided. All together the property was very nice but had potential to be nicer. Also daytime front desk staff were not very helpful and actually cranky sounding. Not so pleasant to deal ..."

Reviewed on 20 Aug. 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG

One West Street, Pittsfield, MA

16 min drive from Tanglewood Music Center

Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...

7.8/10 Good! (863 reviews)

"It was fine , no complaints"

Reviewed on 19 Aug. 2025

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.