Cream Butter and Sugar: In a large mixing bowl, beat the room temperature butter and powdered sugar until light and fluffy, about 2-3 minutes.
Add Vanilla: Mix in the vanilla extract until combined.
Combine Dry Ingredients: In a separate bowl, whisk together the flour and salt. Slowly incorporate the flour mixture into the butter blend, stirring until the ingredients are just combined.
Fold in Cherries and Chocolate Chips: Gently fold in the chopped maraschino cherries and chocolate chips, ensuring they are evenly distributed throughout the dough.
Chill the Dough: Shape the dough into a log, wrap it in plastic wrap, and refrigerate for at least 1 hour (or up to 24 hours) to firm up.
Preheat Oven: Preheat your oven to 325°F (160°C). Prepare a baking tray by covering it with a sheet of parchment paper.
Slice and Bake: Slice the chilled dough into ¼-inch thick rounds and place them on the prepared baking sheet, leaving about 1 inch of space between each cookie.
Bake: Bake for 12-15 minutes, or until the edges are just beginning to turn golden. Be careful not to overbake, as shortbread should be light in color.
Cool Cookies: Let the cookies cool on the baking sheet for a few minutes before transferring them to a wire rack to cool completely.
Serve and Enjoy: Serve these festive cookies on a holiday platter or store them in an airtight container for up to a week.