Preheat your oven to 375 degrees Fahrenheit. Heat a large oven-safe skillet over medium heat and add the olive oil.
Add the diced onion and garlic and cook until the onion is beginning to become translucent.
Add the bacon and cook until the bacon is cooked through but not crispy.
Add the cranberries, thyme, rosemary. parsley, and salt and pepper.
Once the cranberries start to release some moisture, add the wine and let the wine cook down almost completely.
Add the bread cubes and toss well with the other ingredients in the pan, letting them toast a little bit and soak up some flavour. Add the chicken stock and toss until the whole mixture is evenly moist.
Bake for about 20 minutes at 375 degrees Fahrenheit or until the top is crispy and golden brown.
Serve immediately, or cover until ready to serve and reheat uncovered until heated through.
To make a day or two ahead, prepare the stuffing on the stove top and add it to a casserole dish, cover, and store in the refrigerator until ready to bake and serve.