The Berkshires Cheap Holidays 2026

Photo by Photo courtesy of Berkshire Visitors Bureau

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Top Cheap The Berkshires Hotels

Pleasant Valley Motel West Stockbridge

42 Stockbridge Rd West Stockbridge MA

38 min drive from Jiminy Peak Mountain Resort

Stay at this motel in West Stockbridge. Enjoy free Wi-Fi, free parking and daily housekeeping. Our guests praise the clean rooms in their reviews. Popular attractions ...

6.8/10 (1,000 reviews)

"The sheets were clean, the towels were clean, the hard surfaces of the room were clean, the carpet was fairly new and clean. They turned on the heat for us before we arrived, so the room was warm. The beds were uncomfortable and the pillows inside the cases were dingy. There were two small bars of ..."

Reviewed on 19 Oct 2026

Lantern House Motel

256 Stockbridge Road Great Barrington MA

58 min drive from Jiminy Peak Mountain Resort

Stay at this motel in Great Barrington. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Housatonic River and Lake Mansfield Park are located ...

8.2/10 Very good! (455 reviews)

Avoid staying here if you can.

"The fact that they require a vaccine card should be mentioned in their Hotels.com profile. Luckily for me I had it in my car. I don't mind if some hotel owners want to require it, but it should be pretty clearly stated. The owner told me that I didn't need to use the air conditioner, that I should ..."

Reviewed on 22 Nov 2021

The Weathervane Motel

475 South Main St. Route 7 Lanesborough MA

9 min drive from Jiminy Peak Mountain Resort

Stay at this motel in Lanesborough. Enjoy free Wi-Fi, free parking and a garden. Popular attractions Jiminy Peak Mountain Resort and Pontoosuc Lake are located ...

7.2/10 Good! (128 reviews)

"Booked a king bed but when I got there they told me no cable in that room. They gave me a room with a double bed that were on top of being small were very uncomfortable plus so much dust in air conditioner my allergies were affected plus it stunk couldn’t stay had to repack and go drive around and ..."

Reviewed on 1 Oct 2020

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.