Combine first 3 ingredients and 2 tablespoons sugar in a large bowl; cover and chill at least 2 hours.
Beat cream until foamy. Gradually add remaining 2 tablespoons sugar and vanilla, beating until soft peaks form.
Layer 2 tablespoons whipped cream, one half of a crumbled shortcake, and 1/4 cup fruit mixture into each of 8 (12-ounce) parfait glasses. Repeat layers, ending with fruit. Cover and chill 2 to 8 hours. (The longer the parfaits chill, the more the sweet fruit syrup soaks into the crumbled shortcake layers, allowing flavors to blend.)
Top parfaits evenly with remaining whipped cream before serving.
The Vineyard Kitchen