12. Portland, OR
Why you should go: Portland’s pretty rainy year-round. Wouldn’t you rather see it under some snow? You could just use the city as a base for winter adventures in Bend or Mt. Hood. But if you stick around, you can indulge in the city’s rapidly expanding culinary scene, raise pints at more than 75 breweries, and, of course, warm up with the best local coffee.
Why it’s a steal: Catch a flight to Portland for an average airfare of just $274 between December and March. Rooms during the same time go for $159 on average, a 13 percent savings over the fall.
Where to stay: The Woodlark, which is now taking bookings for its opening on December 15 (introductory rates start at $125 per night), unites two historic buildings—the Cornelius Hotel and the Woodlark Building, a former retail and office building built in 1912—into one 150-room property right in downtown Portland.
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