The Berkshires Cheap Vacations 2025/2026

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

5 min drive from Tanglewood Music Center

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

6.6/10 (1,003 reviews)

Easy to park and check in. Walk up window for motel guest check in. The woman was friendly and got us an extra pillow and came to our room to make sure we had heat. The room was out dated, bathroom clean. I felt like I was sleeping in my grandmother's basement. Has a comfortable bed. A little more ...

Reviewed on Oct 13, 2025

Wagon Wheel Inn

484 Pittsfield Rd, PO Box 808, Lenox, MA

9 min drive from Tanglewood Music Center

Stay at this motel in Lenox. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood ...

7/10 Good! (636 reviews)

Beautiful area. Close to Mt. Greylock, Octobrr Mountain and Pleasant Valley Audubon.

Reviewed on Oct 17, 2025

Lantern House Motel

256 Stockbridge Road, Great Barrington, MA

24 min drive from Tanglewood Music Center

Stay at this motel in Great Barrington. Enjoy free breakfast, free WiFi, 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 Nov 22, 2021

See all 1,105 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.