Preheat your oven to 375 degrees F.
Spray a cookie sheet with cooking spray or line with parchment paper.
Slice the cookie dough into ¼ inch pieces. Arrange into a flag shape on a cookie sheet and press the edge together to form one large square cookie.
Bake for 11-12 minutes or until edges are lightly brown.
Allow the cookie to cool completely before decorating.
In a medium bowl, beat cream cheese until smooth. Add the powdered sugar, and vanilla and mix until combined.
Spread the frosting evenly over the cooled cookie.
Remove the tops from the strawberries and cut into quarters.
Create the flag design by placing the blueberries in the top left corner making a small square.
Add cool whip to a piping bag with a star tip.
Create stripes by adding a line of strawberries, then pipe a line of cool whip. Repeat until cookie is filled.
Chill until ready to serve.