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Choose from 1078 The Berkshires Hotel Deals
Vacation Village in the Berkshires
No frills stay with a kitchen and dishwasher (make sure your room has one— some do not!!!). Location is across the street from Jiminy Peak, so skiing can be accomplished almost as easy as staying on their property. This is our fourth time staying and it always serves its purpose.
Reviewed on Dec 30, 2025
Hotel Downstreet, an Ascend Collection Hotel
friendly accommodating staff
Reviewed on Jan 1, 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Staff was very pleasant and friendly. From front desk to valet.
Reviewed on Jan 1, 2026
The Yankee, Trademark Collection by Wyndham
All of the above!
Reviewed on Jan 3, 2026
The Williams Inn
The room was very nice
Reviewed on Jan 1, 2026
Berkshire Mountain Lodge
The hotel was clean all over and the rooms were spacious and clean. Pool was nice. We loved the outdoor hot tub.
Reviewed on Jan 2, 2026
Berkshires Untold
Staff and room were wonderful
Reviewed on Dec 30, 2025
The Red Lion Inn
Wonderful stay in a winter wonderland that evening especially with use of the heated pool and hot tub being maintained! Loved it. Shops inside were lovely as well, bars & restaurant on-site were fun with quirky decor. Whole hotel is quirky, which is fun!
Reviewed on Dec 26, 2025
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
We had an awesome day didnt struggle with anything everything was clean in my room pools are the most cleaned ive ever seen staffs were awesome as well
Reviewed on Jan 4, 2026
Huttopia Berkshires
Healthy food too!
Reviewed on Oct 20, 2025
Hampton Inn & Suites Berkshires-Lenox
Room is clean and staffs are welcoming
Reviewed on Jan 5, 2026
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Nice warm pool and hot tub. Good little fitness center.
Reviewed on Jan 2, 2026
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- Hotels near Jiminy Peak Mountain Resort
- Hotels near Tanglewood Music Center
- Hotels near Ski Butternut
- Hotels near National Shrine of the Divine Mercy
- Hotels near Massachusetts Museum of Contemporary Art
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- Hotels near Bousquet Ski Area
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