Hey, neighbor! We live in Frederick County and also will be driving this year. Good question! Have you posted on the Transportation board yet? Our trip is 7 months away so I haven't honed in on that aspect of our journey yet, but I intended to do a search there or post there regarding the same question as you (except for the pool).
We have driven several times over the years and every time we do, we wind up just driving until DH is too tired to go on, usually South Carolina, and just try to find the cheapest rate we see from the highway. Dumb, dumb, dumb. It never works out. A decent hotel is easy to find but we always pay too much. This year I want to make a good decision and make it in advance.
Aside from consulting the transporation board, you might want to check out a copy or buy a copy of "Drive I-95". The book begins in Massachusetts and goes all the way down 95 to Florida. I don't know if reading it will make a difference. I bought it recently and I've only made it to pages about Connecticut so far.