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Preheat oven to 400°. Line baking dish with parchment paper. Cut squash in half lengthwise and remove seeds. Spread butter over cut edges and in squash cavities. Sprinkle brown sugar on top and bake for 50 minutes or until fork-tender. Allow squash to cool.
Boil water in a medium pot and remove from heat. Stir in couscous and cover. Allow couscous to rest for at least 5 minutes, remove cover and fluff with a fork. Stir in cranberries and diced apples.
In a small mixing bowl whisk together vinegar, maple syrup, salt, pepper and oil. Pour over couscous mixture and mix well to combine.
Fill each squash half with couscous mixture. Return to baking dish; cover and bake an additional ten minutes before serving