Pikachu stars as the central character in the "Pocket Monsters: Pikachu no Fuyuyasumi" animated shorts, a trilogy of winter and Christmas-themed OVAs. Each OVA features multiple segments centered on winter activities and holiday scenarios. These specials diverge from the main Pokémon series by focusing on Pikachu interacting with other Pokémon in self-contained stories, without direct on-screen involvement from human trainers like Ash Ketchum.

Within these adventures, Pikachu dives into various seasonal activities and playful scenarios. These include leading snowball fights, improvising curling games using Meowth as equipment, and exploring winter landscapes alongside companions such as Chikorita. One narrative sees Pikachu and fellow Pokémon embark on a critical mission to find a specific berry needed to heal Stantler, Santa Claus's steed, ensuring Christmas can proceed. Later installments follow Pikachu as he ventures into urban environments, befriending other Pokémon like a pair of Pichu siblings and aiding them during their city adventures.

The shorts highlight group dynamics and cooperative problem-solving among the Pokémon. Pikachu frequently participates in or spearheads group activities, ranging from competitive winter games to collaborative efforts resolving challenges encountered during their holiday experiences. While Ash Ketchum does not physically appear alongside Pikachu in these adventures, his presence lingers through off-screen actions, such as preparing surprises for Pikachu during the winter celebrations. Pikachu maintains his established personality traits of curiosity, playfulness, and eagerness to help others, consistent with his portrayal across the broader Pokémon franchise.