After living in Charlottesville, Virginia, I would 110% recommend visiting for your Bachelorette weekend (or even just a girls weekend in general)! Here is what I would recommend for an itinerary:
Friday:
Arrive at hotel or Airbnb
Walk around the Downtown Mall area
Spa at Boar's Head or Keswick
Get ready for dinner at the hotel or Airbnb
Drinks at the Quirk Hotel rooftop
Dinner at Public Fish & Oyster or Oakhart Social
Saturday:
Breakfast and Coffee at MarieBette
Rent a bus to hop around wineries! I would recommend Pippin Hill, Mount Ida, Jefferson, or Merrie Mill.