Toshi Abe and Nancy Hall, a married couple from Princeton, N.J., bought their unit as a second home after a few memorable trips to the Berkshires.

"One of my friends said, 'You have to do something special for your 60th birthday,' " said Hall, 61. "We came to Lenox and had a wonderful weekend and ended up seeing something that was happening in another month. We came back for the jazz festival, and, while we were there that weekend, Arlo Guthrie was singing in Pittsfield. I told my husband we needed to buy an apartment."