One of our favorite holiday movies of all time is HOLIDAY INN, with Bing Crosby and Fred Astaire. They play two entertainers who part over a woman, and Bing Crosby goes to the country in Connecticut and buys a farm. He turns it into Holiday Inn, open on all the major holidays of the year. It's a glamorous place, despite being in the country, and he manages to put on magnificent productions with sets and an orchestra and fabulous costumes. Fred Astaire's dancing is amazing, and Bing Crosby croons. It's a love story and a musical and a comedy, and if you haven't seen it, you should definitely check it out.
One of my favorite lines in the movie is when the manager goes to the flower shop and asks for "orchids. Loose, looking like they don't care."
In the 1942 film, Bing and Marjorie Reynolds sing "White Christmas," which is one of the best parts of the film: