Line two baking sheets with parchment paper or silicone baking sheets.
In a large bowl, beat the butter and sugar until light and creamy, about 2 minutes. Beat in vanilla extract and then slowly beat in the flour until just incorporated.
Use a cookie scoop to portion out the dough on the prepared cookie sheets, about 1" apart.
Use an inverted teaspoon to press down on the cookies, flattening them and making a small dip in the center of each cookie.
Press a maraschino cherry securely into the indent on each shortbread.
Bake for 12-15 minutes until lightly golden brown.
Cool on the cookie sheet for about 15 minutes.
Notes
Chill: Chill your dough so that it holds it shape well.
Toppings: Try replacing the cherries with crushed almonds.
Chocolate Chips: You could replace the cherry by spreading chocolate chips over the top of the cookie. Or you could keep the cherry but also add chocolate chips for a maraschino cherry chocolate chip cookie
Chopped Cherries: Try chopped maraschino cherries added into the dough or spread over the top of the cookie.
Unsalted Butter: Use unsalted butter and add just a pinch of salt to the recipe.
Cooking Tip: Try baking the cookies low and slow (around 200 degrees) for that light color you desire.
Cherry Juice: Cherry juice from jar cherries can be used in delicious cherry recipes, Shirly Temples or in other cocktail drinks.
Variation tip: Add a little rice flour to the recipe to make that sandy texture.
Drizzle: Drizzle a little icing, dark chocolate or white chocolate on top of the Christmas shortbread cookies.