Experience Bend like a local—or if you’re local, live it up like a tourist—by hanging your beanie at a historic Lavabelles cottage (lavabelles.com, rates start at $150 a night). If it’s just the two of you, opt for “Laverne,” a retro chic one-bedroom with a sleeping loft and mountain views. It’s stumbling distance from the shops and restaurants downtown, and it’s an easy walk to the Old Mill District—which plays host to Bend’s annual WinterFest in February. After a day on the slopes or in the backcountry, head to McMenamins for a dip in the Turkish soaking pool or lounge seating in the movie theater. Passes come with the rental. There are plenty of things to do, see, eat and drink in Bend, but there’s no shame in kicking back and doing nothing. Before you get too cozy, fill your growler at Boneyard Brewery a few blocks away on Lake Place.
Best For: Multisport junkies with a taste for microbrewsThe biggest town on this list, Bend is a fast-growing, adventure paradise of more than 76,000 people in central Oregon that happens to have the region’s premier ski area, Mount Bachelor, 22 miles west up the road. If you ever dream of skiing in the Pacific Northwest, Bachelor is the kind of mountain you dream about. A 9,000-foot stratovolcano lined with high-speed quads and skiable down every side, it’s a huge, diverse area which, being on the drier, east side of the Cascades, has lighter snow than the Pacific cement that coats most mountains in the region.