Position racks in the upper and lower thirds of the oven; preheat to 425 degrees F. Toss the cranberries with the sugar, wine, olive oil, 1 tablespoon rosemary and 1/2 teaspoon salt in a 9-by-13-inch baking dish. Bake on the lower oven rack, breaking up the berries with a spoon halfway through, until bubbling, 20 to 30 minutes. Let cool 10 minutes. Transfer to a bowl, cover and refrigerate until chilled, at least 2 hours.
Meanwhile, coat a rimmed baking sheet with cooking spray. Toss the almonds with the maple syrup, remaining 1 teaspoon rosemary and 1/8 teaspoon salt in a small bowl until coated. Spread on the prepared baking sheet and bake on the upper oven rack until golden brown and bubbling, 10 to 12 minutes. Let cool until hardened, about 30 minutes. Finely chop the brittle and sprinkle on the cranberry sauce just before serving.
Make the sauce up to 5 days ahead; cover and refrigerate. Make the brittle up to 3 days ahead and store in an airtight container; finely chop before topping.