I'm biased, of course, but my hometown of Charlottesville is a great area to visit. You've got historical sites (Monticello, etc.), beautiful mountains and rolling hills, lots of wineries, etc. Plus you're not far from Blue Ridge Parkway and Skyline Drive, with excellent views, hiking, etc. The city itself has plenty of fine dining and a decent nightlife.
There's an airport in Charlottesville, but I'm not sure that would work for your deal? Otherwise you could fly into DC and drive down. Some nice stuff in parts of northern Virginia as well, though I'm not as familiar with all of it.