I prefer early or at least "first thing" in the morning appointments. If I'm going into DC mid-day, I'll take metro which doesn't help Georgetown location.  I never valet park. I've always assumed that wasn't wise.

I would be more inclined to go to G'Town than DuPont..especially dependent upon parking.  While I would never go to DuPont, I would consider Georgetown - I know, just a few blocks, but DuPont and Connecticut and the circle is a hot mess.  Its taken me twenty minutes to just get around the circle (idiots won't let you in) - and thats not a rare occasion.  God forbid you make an error and have to circle around.

Metro is a pain, too, miss a train during non-rush hour and you've potentially added a half an hour to your schedule.

Georgetown you can at least come in the back way through Rosslyn or even walk over.

Georgetown also seems more discreet.  Too many businesses (as in where you work, or friends work - on a daily basis run into work colleagues in the DuPont area, plus people that live there).  around DuPont for a native to be walking around and wandering into a hotel.

People joke with me that I build my life around traffic and parking.  Dupont Circle offers, at least, the hope for a parking space when I've arrived, and I can explore the transit options.  For me, Georgetown may as well be on the moon.

......I would suggest that gentlemen valet park, or spend a few dollars and use Uber.  

Hugs and Kisses,
Kelly

Dupont is much easier if Metro is your means of travel, which for me is a factor. Hate to drive and have to worry about parking.

Uber or plain old taxi service is really the only sensible way to get to and from Georgetown. Park wherever is convenient and take the cab over - it'll be cheaper than valet or street parking, and far more convenient.