Begin by slicing each Twinkie in half lengthwise and laying them cut-side up in a 9x13-inch baking dish.
In a mixing bowl, beat the softened cream cheese with an electric mixer until smooth.
Add the powdered sugar and vanilla extract to the cream cheese, and continue to mix until well combined.
Gently fold in the whipped topping until the mixture is smooth and creamy.
Spread the cream cheese mixture evenly over the Twinkies in the baking dish.
Layer the sliced fresh strawberries over the cream cheese mixture.
Spoon the strawberry pie filling over the strawberries, spreading it out evenly.
Cover the dish with plastic wrap and refrigerate for at least 2 hours to allow the flavors to meld and the dessert to set.
Serve chilled, cutting into squares to enjoy.