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! (446 reviews)

Spacious, clean, nice breakfast

Reviewed on 15 Feb 2026

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 ...

8.8/10 Excellent! (2,263 reviews)

Good size rooms, had everything we needed. Accessible to the main building (wish there were bigger cups for coffee and real milk) but other then that it was great. Front desk was helpful.

Reviewed on 24 Feb 2026

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! (1,002 reviews)

Room was nice and tidy. The staff were friendly. Check-in was quick and simple. Breakfast was plenty with eggs, bacon, sausages, waffles and French toast. There was only 1 working elevator so the wait was slow. Parking was undergoing renovation so you need to park down the slope and walk up. There's ...

Reviewed on 22 Feb 2026

See all 1,104 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.