Roughly six hundred years before the present day, in a now-destroyed kingdom, there lived a girl known only as the Princess Fair. Her beauty was so devastating that all who laid eyes upon her would willingly offer up their lives, and every path she walked became a mountain of corpses. This collection of stories from the Monogatari series Off Season delves into the origins of legendary oddities and revisits familiar faces during pivotal moments in their personal journeys.

The narrative is structured as a series of interconnected tales rather than a single linear plot. It begins with the short fable Cruel Fairy Tale: Princess Fair, which recounts the brutal curse that befell a kingdom because of its princesss fatal allure. This leads directly into the central arc, Acerola Bon Appétit, in which the ancient and eccentric vampire Deathtopia Virtuoso Suicide-Master arrives in the ruined land. Driven by her gourmet obsession to consume the ultimate prey, she seeks out the princess, whose name is Acerola. Instead of a simple hunt, she finds herself repeatedly dying from simply being in the princesss presence, which sparks a strange partnership. Deathtopia takes Acerola to her castle and becomes her mentor, ultimately leading to the princesss transformation into the legendary vampire known as Kiss-Shot Acerola-Orion Heart-Under-Blade, explaining the origin of Shinobu Oshinos original identity.

Shifting away from the distant past, the story continues with Karen Ogre, which follows Karen Araragi as she retreats to the mountains in an attempt to find herself and gain independence. Unbeknownst to her, she is accompanied on her solitary journey by Shinobu, leading to an unexpected and unusual encounter between the boisterous, justice-driven girl and the ancient, donut-loving vampire. The final arc, Tsubasa Sleeping, takes place during Tsubasa Hanekawas world travels in search of the missing specialist Meme Oshino. While in Germany, she crosses paths with the vampire hunter Dramaturgy, who enlists her help in tracking down a pair of rogue twin vampires responsible for abducting travelers, forcing the usually peaceful Tsubasa to confront a dangerous supernatural threat.