Kernersville is right in the middle between Winston and Gboro but the hotels are a little limited there's basically two hotels probably 2.5 maybe 3 star if you stretch it, nice enough though and one is back off the road so a fellas car wouldn't be seen.  Seems like Greensboro is the choice of visiting ladies and really only 30 minutes from Winston so no biggie for someone coming from Winston. A lot of choices near the airport and a few close to the mall. Greensboro is probably better for blending in as far as a hobbyist perspective most of the nicer chain hotels in Winston are near the mall and may be more prone to someone riding by and seeing his vehicle. Downtown is nice but parking can be a pain. I'm sure a lady can give you better input but thought I'd put my two cents in which as you know is worth about a penny.

The Four Seasons area is probably the most central location. Just off I40 so would be a quick trip from Burlington, Archdale and Winston. Some nice places to choose from too.