Place the bowl of an electric mixer, or a large glass bowl if using a hand mixer, in the freezer to chill for at least 10 minutes.
Fit electric mixer with the whipping attachment, then add heavy whipping cream and vanilla to the chilled bowl.
Whip on low speed while gradually adding powdered sugar, then gradually increase speed as whipped cream thickens. Whip until cream can hold its shape, but is not lumpy.
Spread a thin layer of whipped cream into the bottom of an 8 x 8" baking dish.
Layer in 9 of the cookies, spread on another layer of whipped cream and top with 1/3 of the strawberries. Repeat layers—cookies, whipped cream and strawberries—two more times to create three layers total.
Cover dish with plastic wrap then refrigerate overnight.
When ready to serve, slice then serve immediately.