Beat whipping cream, powdered sugar, and vanilla in a medium mixing bowl with an electric mixer or rotary beater until soft peaks form. By hand, fold in yogurt and half of the berries.
Spoon some of the whipped mixture into the bottom of 10-ounce individual glasses.
Top each with some of the remaining berries, the rest of the whipped cream mixture, and then the rest of the berries. If you wish, cover and chill up to 2 hours. Before serving, sprinkle with the crumbled cookies.