How about Oasis? They will set up a private cabana for you overlooking the vineyards and cater anything your heart desires. Or, for really romantic - ask them to set-up a private table in the rows of the vineyard. Complete with crystal, candles, flowers, etc. Ask Tareq to help you out.
Tarara Vineyard in Leesburg. The Cab Franc and Merlot are yummy.
The Lightfoot Restaurant in downtown Historic Leesburg is a very nice restaurant. Good food and atmosphere... not super romantic as it gets pretty busy and the tables are fairly close together. But it is still nicely lighted and romantic in it's own way. They also have a Chef's Table seating. I still haven't gotten to experience it, but i hear it is quite good.
The best is Barboursville Vineyards in Charlottesville - they have exceptional award winning wines (for VA) and very fine, romantic dining, on site. The grounds are gorgeous. You can even stay there now, they have refurbished two old cottages on the grounds and built 3 new suites. I just booked a cottage and am surprising my husband for his bday. I think it's the closest thing in VA to a Napa experience.
I'm told Prince Michel Winery has a decent restaurant (North of of C'ville along Rt. 29) though I haven't been nor have I had their wines.