Larry Olmsted holds the official record for "Most Pistes Skied in 8 Hours," but he knows his number—64—can be beaten. And he wants you to try.

There's at least one major upside to the bursting of the real-estate bubble: The kind of adventure-ready second home you've always dreamed about is suddenly within reach. From mountain retreats to lakefront outposts to slopeside condos, here's your primer on where to invest for the long haul.