Lovely Linda Mason has crooner Jim Hardy head over heels, but suave stepper Ted Hanover wants her for his new dance partner after femme fatale Lila Dixon gives him the brush. Jim’s supper club, Holiday Inn, is the setting for the chase by Hanover and manager Danny Reed. The music’s the thing.
Famous showbiz trio breaks up, as crooner Jim Hardy (Bing Crosby) plans to take his fiancée Lila Dixon (Virginia Dale) out to Connecticut to live on a farm and enjoy the lazy life. The problem is that suave dancer Ted Hanover (Fred Astaire) has stolen Lila from Jim and runs off with her to continue their showbiz careers. Farming does not prove as easy as Jim had hoped and after a year, he ends up having a nervous breakdown. In the sanitarium, Jim comes up with the idea to turn his old barn into a nightclub that is only open on holidays. Jim visits Ted and Lila in New York and tells his old agent Danny to send him any talented acts for his club. Danny encounters a young woman at a flower shop who is bent on a career as a dancer and singer. Her name is Linda Mason (Marjorie Reynolds), and he gives her tickets to a show and tells her to audition at Holiday Inn. At the show she meets Jim and both pretend to be more important than they really are. When she arrives in Connecticut they are surprised to be caught in their lies. Linda auditions and Jim agrees to let her star in his shows beginning with the upcoming New Year's Eve performance.In the meantime, Lila leaves Ted for a Texas millionaire. This starts Ted to drinking, and sends him to his buddy who knows what it is to have the woman you love stolen away from you. When he arrives at the inn he is extremely drunk and ends up dancing with Linda. They dance an incredible improvised comic dance routine that is still a classic. Agent Danny arrives in time to see Linda's back as she walks up the stairs. In the morning when Ted wakes up, he can't remember anything about her but the way that she danced and he know he wants her to be his partner. He and Danny decide to come back to the club on Lincoln's birthday to scout for "the back of a woman they don't know."Meanwhile, Jim has fallen in love with Linda, who can really sing and dance, and he offers her a life at the Inn, and sort of proposes to her. She agrees to stay with him at the Inn and is excited to be sort of engaged. Of course, Ted has also fallen in love with his mystery dance partner who he rediscovers on Valentine's day. He decides to stay at the inn and dance with Linda there. In an elaborate plan to get Linda away from the inn and Jim, Ted arranges for men from Hollywood to watch the 4th of July performance. Jim learns of this plot and decides to sabotage their routine by preventing Linda from arriving that day and inviting Lila, whose millionaire was not who she hoped he would be, to come in her place. In her attempts to get to the inn, Linda meets up with Lila and learns of Jim's plot. When she finally does arrive she is furious with Jim and in her anger agrees to leave with Ted for Hollywood.Jim closes the inn and mopes around. His housekeeper gives him sage wisdom that sends him to Hollywood to get his woman back. He arrives on the day before Linda and Ted's wedding, and sneaks onto the set. Linda gradually picks up signs that he is there and when he finally reveals himself she joyously runs to meet him.The movie culminates with a rewrite of the opening number in which we learn that Jim and Linda will be staying together at the Inn to sing and Ted will resume his dancing career with Lila.Holiday Inn is a Christmas treasure that shows a simpler time in history in a warm and endearing light.