On Christmas Eve, Winnie the Pooh is having trouble setting up his Christmas tree. Pooh slips and falls, and breaks a shelf holding a present he made for Piglet. When Piglet suddenly arrives, Pooh desperately searches for a new hiding place for the present as more of his friends arrive, eventually putting it in an empty honey pot and then helping himself to a full pot of honey with satisfaction, in which he forgets to answer the door. The gang eventually open the door themselves per Roo's advice after wondering why Pooh won't let them in. Although surprised to see Pooh eating honey, they begin helping Pooh decorate his tree. After Tigger briefly annoys Rabbit with jingle bells, everyone joins in and sing a Winnie-the-Pooh version of "Jingle Bells". That night, Roo wonders if Santa is coming. Rabbit tells Roo the story of Winnie the Pooh and Christmas Too which explains of how, on a previous Christmas Eve, their letter failed to reach Santa and that Pooh dressed up as Santa to bring gifts to his friends, but was unsuccessful. After a second failed attempt to deliver their letter, he returns with the bad news, but his friends say that he is more important than presents until Christopher Robin arrives with their presents. After Rabbit finishes the story, Pooh arrives with a sack of gift for everyone. The next day, it is Christmas Day and everyone heads outside to have fun. While playing in the snow, Tigger again annoys Rabbit with his jingle bells, forcing him to take them away. Tigger nevertheless lets Rabbit have them, who then discards them into a tree stump. Sometime later, Piglet gives Pooh some honey pots as a Christmas present. Remembering his own present, Pooh suddenly begins searching for it, but the search lasts until New Year's Eve. When Pooh hears Christopher Robin calling for him, he heads outside to find him. After finding Christopher Robin, he reveals that he is preparing a party to celebrate New Year's Eve, in which Pooh suggests having the party at Rabbit's house. Pooh then takes the box of decorations and heads off there. At Rabbit's house, Rabbit and Piglet are tending to a potted carrot. While Rabbit goes to get the plant food, Pooh suddenly comes in, scaring Piglet into hiding with the carrot. While Pooh examines the honey in the Rabbit's cupboard, Rabbit returns and closes the cupboard, unknowingly pushing Pooh inside, but is shocked to find his carrot gone. A noise in the cupboard leads Rabbit to open it and finds Pooh inside eating honey, to his annoyance. After finding Piglet, another visitor knocks on the door, which turns out to be Tigger, followed by Eeyore emerging from the snow underneath them after Tigger bounces Rabbit. Tigger further annoys Rabbit after failing to catch a self-thrown snowball that lands in his house. When Pooh informs them of the party, an excited Tigger tries to decorate the place, but ends up making a mess, making Rabbit so angry that he throws everyone out, planning to move. Believing that their personalities are a threat to Rabbit, Pooh suggests doing a resolution, a promise which they must keep no matter what. Piglet starts behaving like Tigger, Tigger starts behaving like Piglet, Pooh starts behaving like Eeyore, and Eeyore starts behaving like Pooh. As Rabbit prepares to move, his four friends return with their changed personalities, which immediately makes him leave, but after falling down a cliff, he is sent flying with his carrot. His friends find him stuck in a tree with bees attempting to abduct him. The four then regain their old personalities and Tigger unties the rock from his tail and rescues Rabbit. Rabbit reconciles with his friends, convincing them to just be themselves while admitting that he's the one who needs to change just as Christopher Robin arrives. The gang then head back to Rabbit's house to prepare for the party. Later at night and at the start of the New Year, Rabbit returns the Jingle Bells he took from Tigger. Pooh finally remembers where he left Piglet's gift and goes home to get it. After returning with the honey pot containing the present, revealed to be a music box, he then gives it to Piglet. After singing a song to Piglet following the music, Piglet claims that Pooh is a greater gift and everyone sings "Auld Lang Syne" to celebrate the New Year.
The film was released as a direct-to-DVD on November 12, 2002. The film was released for the first time on Blu-ray on November 5, 2013 as the "Gift of Friendship Edition", the same day as the 30th Anniversary Blu-ray release for the 1983 animated featurette Mickey's Christmas Carol.
