We were there last year after Xmas through New Years
We're all novice skiers/snowboarders. It wasn't crowded to us at all. It didn't snow, but snow was made and we were able to ski and my sons attempted snowboarding, though they both hurt their wrists the first day and didn't attempt anything after that. I wouldn't worry about it being too crowded. For us, it was just a very laid back and relaxing vacation. We had some plans to visit wineries in the area, but got into the relaxing part to the point we didn't do anything. We're going to try the skiing and snowboarding again this coming year the third week of January. We're all looking forward to it. Massanutten is so big and has so much to do, I would go for it!