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 11 Dec 2025

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

13 min walk from Jiminy Peak Mountain Resort

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 ...

8.6/10 Excellent! (2,170 reviews)

Awesome for ski

Reviewed on 14 Dec 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG

One West Street Pittsfield MA

18 min drive from Jiminy Peak Mountain Resort

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! (988 reviews)

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

Travellers 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 15 Dec 2025

See all 1,086 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.