If you are planning on flying, the easiest airport by far is Charlottesville (CHO). You may find better deals by flying into Richmond (RIC), but have to drive about 75 to 90 minutes. Unfortunately there is no easy way to use mass transit from Richmond to Charlottesville.
If you prefer not to fly, Charlottesville’s Amtrak station is right downtown, and an easy walk to hotels and the wedding venue.
Both Lyft and Uber are available in town.