The structure of the episode is similar to the structure of the Treehouse of Horror episodes, only that it is divided in four stories instead of three.
Bart is nettled because he didn't get the dirt bike he asked for over the last three years and vows to stay up untill midnight to shoot Santa. He falls asleep later and dreams that a train (In a parody of The Polar Express), driven by Otto Mann, lands in front of the house and flies him to the North Pole. After Bart works his way up the corporate ladder, he is able to meet Santa (Krusty) who has run out of money since giving away free presents and getting cookies in exchange is not a sustainable business. Bart chooses not to shoot Santa and as soon as he walks out, Santa throws a big party in his office. Taking off, the train is chased by police cars. Otto jumps off the moving train, leaving Bart stranded on board.
In Lisa's dream, it is WWII as Marge is fighting while Homer is taking care of the kids. During Christmas, Homer buys a Christmas tree to the despair of Lisa who is traumatized because last year she went to buy a tree with Marge only to find out that her mother was called to war. Marge's war scene ends with a reference to the theatre act from the film "Inglorious Basterds" after which she goes back home to her family. It is then revealed that this segment was just a dream that Lisa had.
In Marge's dream, she receives a night time visit from the most powerful force in the universe who teaches her the 'true meaning' of Christmas: Martha Stewart.
In the final segment, Maggie sleeps with a "Fluppets" videotape and dreams that the family appears as puppets (as a parody of the Muppets) in a theatre as they prepare to leave for Hawaii, leaving Moe to take care of their place, in the company of his girlfriend, Katy Perry (After her controversy on Sesame Street). In the end of the episode, Mr. Burns arrives telling everyone he has received a visit from three spirits making an allusion to "A Christmas Carol". And finally they sing a rendition to "The Original, Unabridged 39 Days of Christmas".