Place the cream cheese in a microwave safe bowl and microwave 30 seconds or until soft enough to stir. Stir in the sugar and vanilla. Let it cool so it's barely warm.
Dust a large cutting board or work surface lightly with flour and unfold the puff pastry. Spread the cream cheese in an even layer from edge to edge leaving a 1-inch border on the end farthest away from you.
Sprinkle the chopped cranberries evenly all over the cream cheese.
Roll the pastry up and cover with saran wrap. Refrigerate 20 - 30 minutes or up to 24 hours.
Preheat the oven to 400 degrees F. Line a large baking sheet with parchment.
Use a serrated knife to slice the puff pastry into ¾ to 1-inch thick rolls. Place them on the baking sheet 1 to 2 inches apart.
Bake 14 - 18 minutes until puffy, golden and cooked in the center.
Let cool 5 - 10 minutes.
In a small bowl whisk the confectioners' and milk together to make a glaze.
Drizzle the glaze over the roll-ups and sprinkle with almonds.
They're best eaten fresh! Reheat the leftovers 2 at a time on a napkin or paper towel about 10 seconds.