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

37 min drive from Jiminy Peak Mountain Resort

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! (483 reviews)

"Great location for an October getaway. The room was more than comfortable."

Reviewed on Oct 29, 2026

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

13 min walk from Jiminy Peak Mountain Resort

A garden and in-room fireplaces await at this romantic aparthotel, which also offers a terrace and an outdoor pool.

Holiday Inn & Suites Pittsfield-Berkshires by IHG

One West Street Pittsfield MA

18 min drive from Jiminy Peak Mountain Resort

A garden and onsite dining await at this romantic hotel, which also offers a terrace and a bar.

See all 1,073 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.