Wrap each water chestnut with a half strip of bacon. Insert a toothpick through the center with the seam-side down. Place in a baking dish. Continue wrapping all the water chestnuts, creating a single layer in your baking dish.
Bake in a preheated oven for 30 minutes or until the bacon is cooked. Drain off the grease. Be careful when doing this because the pan and grease will be extremely hot.
In a medium bowl, whisk together the mayonnaise, brown sugar, chili sauce, and cranberries. (For the cranberries, I like a mix of whole cranberries and cranberries that I’ve sliced in half.)
Pour the sauce over the bacon-wrapped water chestnuts. Return to the oven and bake for another 30 minutes. Serve warm.