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! (414 reviews)

Everything was great— the cleanliness, the plentiful breakfast, the character and coziness, and the proximity to Amici across the street (free dessert with your room key).

Reviewed on 2026/1/13

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! (2,213 reviews)

Room is great for families. Bit dated but clean and spacious.

Reviewed on 2026/1/20

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! (1,001 reviews)

Couples like: onsite spa services, bar, winery tours

Travelers say...

generally good

Reviewed on 2026/1/19

See all 1,071 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.