During our search for a place to hold our family reunion this Spring, my wife and I "tested" the Wainwright Inn. We liked it so much, our extended family of 15 will be spending a May weekend there.
Rooms are nicely appointed, living room very cozy, and the breakfast was fantastic. Rates are $145-$195, including the breakfast, so easily a better value than the chain motels.
Somewhat noisy because it is on the main road, but rooms in back uneffected. Easy walk to all Great Barrington sites.
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