Preheat the oven to 425F and line a baking sheet with parchment.
Whisk together the butter, sugar, baking powder, and salt. Cut in the cold butter, using a pastry cutter or your fingers.
Mix the cranberries and dark chocolate into the dry mixture.
Combine the vanilla with the cream, then add it to the dry mixture and stir gently until barely cohesive. Turn out onto a floured surface and pat into a 1″ thick circle. Use a knife or biscuit cutters to divide the dough into 8-10 pieces. Arrange on the baking sheet at least 1″ apart from each other.
Bake for 16-18 minutes, or until the tops are golden and no part of the scones looks wet.
Remove from the oven and allow to mostly cool before combining the milk and powdered sugar, and drizzling over the scones.
Store in an airtight container at room temperature. Best within 2 days.