Virginia Winery Wedding from Dc?

I highly recommend having your wedding ceremony and reception in the same place.

Your idea can be done but keep in mind it eill involve more expenses and thorough planning. I visited a lovely winery in Reston, VA a few years ago.

My advice would be to research the area. We got married four hours from where we live in an area neither of us were familiar with. I did s ton of research to see what restaurants were in the area and fun things to do. We got married at a hotel so I didn't do any research on that.

You could definitely make it work. I'd just try to make sure the venue is around 30 minutes or less from the church. If it's in your budget, providing a bus or shuttle would be appreciated by guests (especially to avoid driving in DC), but it's normal for guests to drive themselves to the reception.
Big, fancy hotels are scarce near the VA wineries I've been to since they're all in the middle of nowhere, however you can usually find mid-range hotels like holiday Inn express or Hampton Inn within a reasonable distance.
Most guests normally just come in town for the wedding, so you don't really need to suggest things for them to do, but if you choose to, I would just suggest things in DC. There really isn't anything too exciting in Northern VA other than additional nearby wineries or breweries lol

Also District Winery in DC would allow you to have the best of both worlds. But fair warning, their wedding prices are super high depending on your budget