You can leave the boat in the
water in the Chesapeake, if that is your question. It really will not need more than draining the
water pipes that might freeze on a bad day and
antifreeze in the
engine coolant.
In the southern Chesapeake I love the pretty little harbor of Urbanna on the lower Rappahanock River, but there must be many more in the area. Irvington comes to mind as well, and has
marinas. Both are largely rural, not the urban areas north (Annapolis) and south (Norfolk).
Local note: Norfolk is pronounced Nor F**K, leading the the Norfolk Academy Cheer from the 1960s "We don't smoke, We don't drink, Norfolk! Norfolk!
We sailed in that area right through the
winter, although it did get a mite blustery.