Preheat oven to 375°
Pierce both acorn squash with a sharp-pointed knife on both sides. Place in a microwave-safe dish and cook in the microwave for 6-7 minutes on high until squash is soft and can be easily cut in half.
While squash is in the microwave, heat olive oil in a frying pan and saute onions and apples. Add cranberries in the last few minutes and allow them to soften. Remove onions, apples, and cranberries and set aside.
In the same pan just used for onion mixture, cook the chicken sausage until no longer pink, breaking sausage into small pieces. Add apples, onions, and cranberries back to pan and season with poultry seasoning, salt, and pepper.
Add the cooked rice to the pan with sausage and apple mixture, combine well, and heat 3-4 minutes.
Remove squash from microwave, cut each one in half, and remove seeds. Place into a baking dish. Divide rice/sausage mixture into 4 equal parts and place into the squash halves.
Pour 1/2 cup of water into the bottom of the baking dish, cover with aluminum foil, and place it into a preheated oven. Bake for 30 minutes.
Drizzle balsamic glaze over each squash, if desired.