The Berkshires Cheap Holidays

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Pleasant Valley Motel West Stockbridge
Pleasant Valley Motel West Stockbridge
2 out of 5
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 ...
6.8/10 (978 reviews)
"No real bells of whistles. It was quiet, clean. The price was fabulous compared to all other properties in a 10-mile radius. The Manager was very pleasant and always smiling. Right off the Mass Turnpike in West Stockbridge just before entering NY. Again for 1-2 nights I will always return."

Reviewed on 7 Jul 2025

Pleasant Valley Motel West Stockbridge
Wagon Wheel Inn
Wagon Wheel Inn
2 out of 5
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! (608 reviews)
"Convenient location for my trip"

Reviewed on 6 Jul 2025

Wagon Wheel Inn
Lantern House Motel
Lantern House Motel
2.5 out of 5
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 22 Nov 2021

Lantern House Motel
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.