Tom,
We did Skyline Drive the end of May 2002 on the way down to Washington DC for the Rolling Thunder rally ( Harley thing ). The weather was perfect.
Views :
http://www.geocities.com/nickcats/views.jpg
http://www.geocities.com/nickcats/back.jpg
http://www.geocities.com/nickcats/vegas.jpg
http://www.geocities.com/nickcats/smoke.jpg
http://www.geocities.com/nickcats/riding.jpg
Unfortunately, since DC was the final destination we stayed at the cheapest places possible on the way down, so I can't really recommend any lodging.
Great trip & beautiful country ! Have a great time...
Nick