The Berkshires Cheap Holidays 2026/2026

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 ...

6.6/10 (1,000 reviews)

Quite , clean , very good all around.

Reviewed on 2 Dec 2025

Wagon Wheel Inn

484 Pittsfield Rd Lenox MA

25 min drive from Jiminy Peak Mountain Resort

Stay at this motel in Lenox. Enjoy free Wi-Fi, free parking and daily housekeeping. Our guests praise the helpful staff in their reviews. Popular attractions ...

7/10 Good! (641 reviews)

Good overall.

Reviewed on 26 Oct 2025

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 ...

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

See all 1,085 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.