It is the year 1698, seven years after Simon Belmont originally defeated the evil Count Dracula. After Simon delivered the final coup de grace to the Prince of Darkness, the Count placed a dark curse upon him that would send him to an early grave unless Simon revived him. Moreover, Dracula's minions are once again stirring throughout the land of Transylvania, ravaging throughout the many villages and terrorizing the townsfolk. Simon takes up the legendary whip, the Vampire Killer, once again and travels throughout the land to the towns of Jova, Veros, Aljiba, Aldra, Oldon, Fetra and Ghulash to liberate the people and seek help from them as he searches for the Count's body parts which have been hidden in five different dark manors (Berkeley, Rover, Brahm's, Bodley and Laruba) throughout the land.
The game includes three different endings, determined by how long it took for the player to complete the game and how many continues were used. All three are variations of the same ending, but with different twists featured. The 'good ending' is conical.
Simon's Quest's environment differs from the linear castle of the first game, and is instead an open-ended landscape interspersed with towns, cemeteries, manors and dungeons. The passage of time in game causes day to become night and vice versa. Enemies are stronger at night, zombies invade towns and the townspeople are nowhere to be seen as they are hiding in their houses from the monsters. New to the series are several RPG elements, such as an inventory and a leveling system which causes Simon's health to increase whenever he collects a specific amount of Hearts. During the day, townspeople offer hints (although the player must be aware that some of these may be half-truths or outright lies), and merchants sell items (such as whip upgrades) in exchange of Hearts. The amount of time it takes to complete the game also affects how well Simon fares at the ending