I really like the Eagle idea, but it might also be worthwhile to keep an eye on Grand Junction flights, since the drive time to Steamboat ought to be less than from Denver. Laramie's actually the closest non-mountain airport, but if we get bad weather, it seems that Wyoming gets sheer misery, so that's perhaps not such a good plan. In good weather it is only a bit more than 2 hours, though. Colorado Springs is a no-win all the way around -- you add hours of drive time, the airport's southeast of the city and the city traffic is like molasses, then you have to get over Monument pass, which is in itself nasty in bad weather and subject to fog fairly frequently, and then you have basically the same drive you would have had from Denver.
Generally I wouldn't expect huge snow problems at Christmastime -- but then there are year like 2006, when we had two huge blizzards in a week and everything got shut down. But at that point nobody gets anywhere, so it probably doesn't matter.