Best of both worlds...
I live in Madison (MSN) and have a place on the Oneida/Vilas county line, just west of Minocqua (ARV). Best of both worlds, and I/my family are very fortunate to have the place in Minocqua, no question. IMHO, best place in the world, almost year-round. Winters are cold, but the snow is great (usually) and the summers can't be beat. Here's a little-known fact about mosquitoes (at least in Minocqua): if you can hold out from about 9:15/9:30 to about 10:15/10:30, they don't bother you after total darkness. Good for beers on the pier after fishing.
ARV is a great airport, as are Eagle River (EGV) and Rhinelander (RHI). RHI has an ILS and air service by NWAirlink (Mesaba) and Midwest Airlines through Skyway. No RJs there yet, though. Perhaps one day.
If you can't find a place in the OSH immediate area, I would recommend Madison, either downtown or east/northeast side. Great city, lots to do if you're not going to be at OSH each day. It's a very easy drive from that part of MSN to OSH, less than 1.5 hours on US 151 which is four lanes and 65 mph from MSN to just northeast of Waupun, then it's Highway 26 from there to OSH (watch out in Rosendale for their notorious speed traps - no exaggeration, they must pay for two new squad cars a year minimum, what with OSH and Packer game attendees who forget to slow down from 55 to 30 on the outskirts of that sleepy little town).
Usually, I go for a day, departing the near west side of MSN around 7:30 a.m., arrive OSH at about 8:45, park, hop the bus at the museum and hit the exhibition halls before lunch, then it's out to the flight lines. We're very fortunate to have EAA's annual fly-in so close.
I think there will be better attendance this year than in recent years because the Scaled Composites/Virgin Global Flyer, SpaceShipOne and White Knight will all be there. It has seemed that recently they have not had unique aircraft on display since the Concorde was last there. I am hoping for a visit by a F-22 this year. Seems that they have enough of them now that perhaps they can spare one for a few days to send to EAA.
See you there!! PM me if you'd like a recommendation on hotels in this area.