These are some less obvious holiday films that I will be watching between now and New Year's Eve.
The Apartment (1960) with Jack Lemmon and Shirley MacLaine. This sardonic, sometimes dark but ultimately heart-warming film takes place over Christmas and New Year's. Wintery Manhattan in wide-screen black & white at the dawn of the 1960's.
Bachelor Mother (1939) also takes place over the Christmas Holidays, beginning in the toy department of a department store on Christmas Eve --- just before Ginger Rogers receives her pink slip and finds herself mistaken for the mother of an abandoned baby. Again, plenty of snowy New York scenes. Funny and full of charm.
If you like starry-eyed nuns who believe they can get cynical rich guys to donate expensive land to charitable causes while speeding around in jeeps and competing in tennis matches (and lots of snowy scenes of Connecticut hillside locales) then Come to the Stable (1949) might be right up your alley.