If you have to be inside Winchester, so be it, but there are great places just outside Winchester that would be easier on the wallet and better for relaxation. You may even want to consider Martinsburg, WV.
There are studio apartments in Winchester to rent on a month to month basis... here is a pretty good one: Candlewood Suites 1135 Millwood Pike
Winchester, VA 22602 United States (USA). That way you can only bring your clothes and leave the rest packed and in storage... you will only have to move one time.....
Relative to housing prior to 1945, there is a historic distric in Winchester.... They call it Olde Town. Check out the site at http://www.nps.gov/nr/travel/VAmainstreet/win.htm If you would like me to refer you to a great agent let me know.... Glenda Marks 980-322-2532