In a large bowl, beat cream with an electric hand mixer or stand mixer with fitted paddle attachment until stiff peaks form, about five minutes. Add in sugar and vanilla and mix well. Set aside.
In the canister of a blender, puree strawberries until it becomes a thick liquid. Set aside.
Spoon whipped cream in bottom of a glass or dish, filling about ¼ of the way full. Layer with strawberries and then top with whipped cream. Repeat with the rest of servings.
Serve immediately or refrigerate until ready to serve.