Milky Season is a visual novel that follows the story of a young student who becomes the head of the girls' dormitory. This new role puts them in many awkward and romantic situations where they can choose how the story unfolds and which girl they may fall in love with, based on their decisions during conversations. The game takes place in a slice-of-life setting that focuses on the story and interactions with characters.
The gameplay features twelve heroines that the player can interact with, allowing them to gauge the affection of eight possible love interests throughout the game. However, animation is absent, and character attitudes are conveyed through voice acting and static poses only. Gameplay elements typical of visual novels include the ability to toggle dialogue text to view clear backgrounds or explore how choices may affect the story's path.