Preheat the oven to 350 F. In a large bowl, mix together butter and powdered sugar until fluffy. Add in the vanilla extract and flour and mix until combined.
Roll the cookie dough into balls and flatten slightly. Place onto a large ungreased baking sheet. Bake for 10-12 minutes. Place chocolate chips into a microwave-safe bowl, and heat in the microwave in 30-second intervals, stirring well until it is fully melted and smooth.
Dip each cookie in the melted chocolate and set onto a plate. Let sit until it is fully set.
