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 15 Feb 2026

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

35 min drive from Tanglewood Music Center

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

8.8/10 Excellent! (2,305 reviews)

Hot tub and pool both clean and well maintained

Reviewed on 15 Mar 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 ...

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

Couples like: on-site spa services, bar, winery tours

Travellers say...

yes

Reviewed on 16 Mar 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.