Home Alone is just a classic. I love the National Vacation Christmas movie, when they go out and get a tree or when the cousin arrives. Great movie. I thought Elf was pretty good. The Grinch movie with Carey is alright, but too long.
Then there are some that I can watch once and they'll entertaining. The likes of Deck the Hall (with Danny DeVito) and I think there's one with Steve Martin where he's trying to go on a vacation. I just try to stay away from the Hallmark Channel or Lifetime movies as they seem to be extremely cheesy and poor quality.