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 breakfast, free parking, and daily housekeeping. Popular attractions Ebenezer II Gifts and Antiques and Hotchkiss ...

9.6/10 Exceptional! (407 reviews)

Clean quiet and relaxing

Reviewed on 2025/11/19

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 condo, which also offers a terrace and an outdoor pool.

8.6/10 Excellent! (2,166 reviews)

Clean spacious toom

Reviewed on 2025/12/6

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.

8/10 Very Good! (979 reviews)

Couples like: onsite spa services, bar, winery tours

Travelers say...

Clean room, convenient and tasty restaurant

Reviewed on 2025/12/5

See all 1,085 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.