If it is cold sleeping that you're worried about, you can go to the Porcupine Mountains in the UP. The have cabins and yurts up there that you can rent. It is pretty pleasant in the winter to be toasty warm in a cabin while staring out the window at a frozen lake.
You ought to be able to string together a 4 day route between cabins.
As for warm locations near by, I'm still trying to figure that one out…