Preheat oven to 375°F. Grease a muffin pan with nonstick cooking spray.
Open and unroll crescent roll dough. Separate dough into two rectangles. Pinch the seams together.
In a medium bowl, stir cream cheese, powdered sugar, and vanilla extract together. Spread cream cheese mixture evenly over each dough sheet.
Add the cherry pie filling and spread it evenly over the spread out cream cheese mixture.
Carefully and gently roll up crescent dough sheets, one at a time. Start at the short end.
Cut each roll into four equal pieces.
Add each slice into the muffin cups of your prepared pan. Bake in the preheated oven for 18 to 20 minutes or until the dough is golden brown.
After removing from the oven, let muffins cool in the pan until they're safe to touch, then transfer to a wire cooling rack.
Prepare the glaze while the muffins cool. In a small bowl, whisk together the milk, vanilla extract, and sugar until smooth. Drizzle the glaze over the top of the muffins before serving.