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! (465 reviews)

"The Shaker Mill Inn is located in West Stockbridge so it is away from the dense tourist traffic in Stockbridge, but is located with easy access to Tanglewood, Stockbridge, Norman Rockwell Museum, and I90 and the rural Berkshires. The garden was wonderful with many flowers in bloom—very pretty. The ..."

Reviewed on 27 Jul 2026

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

35 min drive from Tanglewood Music Center

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

8.8/10 Excellent! (2,487 reviews)

"While not a top-notch place to stay, for the price it is a good value particularly given that you have more space for less cost than just a good motel room and can do some cooking and meal prep on your own. The check-in is always smooth and the accommodations reasonably comfortable. Setting is very ..."

Reviewed on 30 Jul 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 ...

See all 1,087 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.