I'm thinking of adding on to a planned Chicago trip next summer. I would like to add on Door County Wisconsin. Is it more advantageous to stay in a cottage for a week, or to motel hop around the county? I'd love to hear pros and cons of each.

I'm assuming that by "motel hop around the county", you mean moving from hotel to hotel? I don't see any advantage to that. The county isn't that big!

ttt

Just find one place since everywhere else is within easy reach. I personally stay just outside Ephraim at a motel which is quite comfortable. I can reach any other place on the peninsula in less than 45 minutes.

NOTE: Ephraim is "dry" although you are not far from bars or restaurants which serve alcohol located outside the township.

Get on the internet and surf around until you find something in your price range that looks good.

stay at main street motel, fish creek, wi.
quaint, reasonable, family owned. central to everything.
need a car. can rent bikes. beautiful countryside.
check out Pennisula State Park.