Home Alone, Christmas Vacation, Elf, Bridget Jones Diary and How the Grinch Stole Christmas are my favorites.
Yes.
Elf and Bridget Jones Diary are feel-good movies, like sipping on hot chocolate.
Note to OP:
Elf may be a hit or miss for some people, because there are people who think Will Ferrell's naive character is annoying. I personally like his child-like character he portrayed in Elf, unlike his arrogant Ron Burgandy character from Anchorman. I think he's actually adorable when he plays innocent characters (kind of like that man from the Mean Landlord video). Oh, and Zooey Deschanel is it, and this time she's not the manic pixie dream girl since Ferell kinda played the manic pixie dream boy.
Bridget Jones Diaries is pretty funny. The target audience for this movie is usually 18- 20's ladies, but I was sixteen when I discovered that movie. I thought it was cute then, and I still think it's cute now.
The Lifetime channel airs some pretty interesting Holiday stuff. Lol. Their movies are kind of "cheap", but it's still something! There are a lot of movies about family and love <3!
I don't know if you're into non-English sophisticated films, but Ingmar Bergman's Fanny and Alexander takes place during Winter Holidays-- you can get a glimpse of how Yule is celebrated in the 1900s.
The Muppets Christmas Carol-- again, this movie is really cute and funny. Heck, any Muppet movies are great Christmas movies even if they don't take place during winter time.
Christmas on Mars-- you might not like this one since this is sci-fi musical (experimental, psychedelic) featuring the Flaming Lips, but I'm just going to throw this in for others.
T.V. Shows + Christmas Specials:
Hey Arnold
PBS Arthur
Rugrats (family traditions, multi-cultural-- I can totally relate to the Rugrats babies with their experiences)
Adventure Time-- Yay, Christmas sweaters.
The Muppet Show