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! (408 reviews)

Super friendly & the room is adorable! Simple check in. The room was spotlessly clean. We had a great stay. Thank you!

Reviewed on Dec 11, 2025

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! (2,169 reviews)

Your staff is very courteous and yes my room was spotless.

Reviewed on Dec 13, 2025

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! (988 reviews)

Couples like: onsite spa services, bar, winery tours

Travelers say...

Very clean and timely and efficient and the lady who checked me in named Valerie did an amazing job and was very informative and helpful .

Reviewed on Dec 15, 2025

See all 1,084 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.