A few years ago, I made a similar post, which will give you several more recommendations. These movies aren't themed for the winter holidays, but they're fun to watch on a cold night with a warm drink, like hot apple cider with rum, and they're (mostly) family-friendly. (Yes, even The Maltese Falcon can be fun for the whole family... why not.)
Title: Cinderella (1997)
Director: Robert Iscove
This is a Rodgers & Hammerstein musical adaptation of Cinderella, set in a pretty Disney version of a European town. The stepmother's house looks like it's made of stained glass and melted crayons. I like how vivid all the colors are in this one, including the lush blues and purples of the ballroom scene.
The cast is vibrant. Whitney Houston plays the fairy godmother, Bernadette Peters is the stepmother, Whoopi Goldberg is the queen (an opinionated lady who makes squeaking noises of dismay), and Jason Alexander (best known as George Costanza on Seinfeld) is a royal servant with an Italian-ish accent and a song-and-dance number about the upcoming ball.
Paolo Montalban is cute as the prince, and Brandy Norwood plays a lovely, fragile-looking, and sometimes vacant-looking Cinderella. I like how, even before the prince finds her at the end, she decides to leave home, knowing that she deserves a better life than the one she has with her stepmother and stepsisters.
Title: How to Steal a Million (1966)
Director: William Wyler
Language: English and some French
Rating: Not rated
This movie has the absurdity of a screwball comedy. The leads, Audrey Hepburn and Peter O'Toole, associate under highly improbable circumstances and look beautiful while doing so. (O'Toole is so damn charming here. Reminds me a little of Peter Wimsey - intelligent, doesn't appear to take much seriously, but is more serious than he appears.)
Anyway, Hepburn plays Nicole, the daughter of an art forger who passes himself off as an art collector. He's a Wizard of Oz type of scoundrel. One thing leads to another, and Nicole realizes that to keep her father's crimes from being discovered, she'll have to steal a statue he loaned to a museum. Simon (Peter O'Toole's character) arrives on the scene as a burglar who may be able to help her. Or so she thinks.
Title: The Intern (2015)
Director: Nancy Meyers
The Intern is best enjoyed as a magical butler/nanny movie. A preternaturally calm and competent servant (or in this case, intern) steps into the life of a rich, busy, frazzled person (here the founder and CEO of a startup) and makes life a little easier, a little smoother, offering advice, tidying things up.
The intern is Ben (Robert De Niro), a retiree and widower who wants to stay active. He joins a special program at a Brooklyn-based startup founded and run by Jules (Anne Hathaway), who is doing quite well, but also has to shoulder a lot of professional and personal stress. Ben is there to help with some of that stress. He'll offer wisdom, chauffeur services, and home invasions for the purpose of deleting emails sent to the wrong person.
The characters sometimes comment on gender expectations or generational differences, but in a trite way, as if the dialogue has been lifted from magazine or blog post titles. The movie isn't worth watching for its social commentary but for other things. There's a sweetness in Ben and Jules, and their relationship is lovely to watch; it's nice seeing a relationship between an older man and younger woman that doesn't turn her into the object of his last spurt of sexual desire before death. I liked looking at some of the leafy streets of Brooklyn, which I've walked through, and watching the inner workings of a fictional startup (I found this post on what may be accurate or inaccurate about how the movie portrays startups).
One of the funniest scenes involves Ben breaking into a home to delete an email, especially because De Niro has a history of playing criminals who organize heists. Here all he needs to do is work with three endearing putzes of the Millennial generation to find a key under a potted plant and identify the correct laptop before a simple home alarm system goes off.
Title: The Maltese Falcon (1941)
Director: John Huston
Rating: Not rated
This movie is gripping and has some dark twists, but it's also surprisingly funny. The characters are an entertaining pack of deviants. Probably the least unethical one among them is a private detective, Sam Spade (Humphrey Bogart); will he ultimately choose to be law-abiding and involve the police because it's the right choice to make, or because he knows he won't be able to get away with committing certain crimes? He's looking out for himself, as are the rest of them.
They include the frog-eyed and effeminate Joel Cairo (Peter Lorre), the sly and corpulent Kasper Gutman (Sydney Greenstreet), and the winsome Brigid O'Shaughnessy (Mary Astor), who is my favorite femme fatale in the film noirs I've watched so far. She isn't the dangerous blonde bombshell you typically see in such roles. She looks more like a careworn, pretty schoolteacher, the sorrows of the world in her eyes, and what a frightfully clever liar she is. I like how honest she can be about her dishonesty. In one scene, she cops to being a liar; just accept it, it's how she is, she'll admit it without malice or pride.
Bogart's insolent grin is also fun to watch. Throughout the movie there's an undercurrent of fun. The Maltese Falcon itself (a priceless statue of a bird) is so much less important than all the machinations and memorable performances that make the movie riveting.
Title: Mary Poppins (1964)
Director: Robert Stevenson
What's truly magical in Mary Poppins is how all the chimney sweeps have the energy and lung capacity to dance after a long day of work. Given how Bert (Dick Van Dyke) breathes in some soot as if it's a puff of fresh air from the countryside, maybe there are magical properties in the pollution.
Rewatching this movie as an adult, I still enjoyed it, but some things changed. Dick Van Dyke's "Cockney" accent got grating after a while. Mr. Banks (David Tomlinson) became a more poignant figure to me. And when Mary Poppins (Julie Andrews) knocks all those nanny applicants away with a gust of wind, I found myself wishing them well and hoping they could still find work. I mean, Mary doesn't need a job, does she? She lives on a cloud. She can go have a tea party on a ceiling with Uncle Albert (Ed Wynn) whenever she wants.
Julie Andrews is delightful, mixing primness and warmth in her performance, and giving Mary an effortless confidence that makes her completely at home anywhere. The songs are wonderful, one after another, and there are some genuinely moving moments and beautiful visuals. And those chimney sweeps can dance.
Title: Murder on the Orient Express (1974)
Director: Sidney Lumet
Language: English mostly
Years ago, I read the Agatha Christie book this is based on, and I remembered the ending. But even if you know how it ends, you can still enjoy the movie. The answers produced by the sharp, fussy, and largely tactless Hercule Poirot (Albert Finney) are less important than the journey. A journey on a famous train that gets stuck in the snow, after which a passenger is found stabbed a bunch of times.
The suspects are played by a variety of well-known actors, including Ingrid Bergman, Lauren Bacall, Anthony Perkins, John Gielgud, and Sean Connery. Though the movie deals with a sad situation (the root motive for the murder) and has an uneasy ending, it also has some genuinely funny moments and isn't terribly dark or deep. Overall, it's an enjoyable movie, if you want some murder mystery entertainment, and the interiors of the train, the colors and lighting and ornate fixtures, are pleasant to look at.