In Connellesville, I've stayed at the motel 2 miles out of town - up the daugting Rt 119. Not great - I think they might have a B&B in town by now, though.
I've wondered about a route from the Rt 199 motel down to the trail - when goihng east on the trail, you still have to 2 or 3 miles west to get back on the trail. Has to be a way to just go down that hill.
I find the town of Ohiopyle to be a little unsettling. Seems the town folks don't like the tourists too much and there are plenty of arrogant, wealthy tourists to justify that.
I like staying at the River's Edge in Confluence.
In Rockwood, I highly reccomend the Gingerbread House - About 200 feet to the right up Rockdale Rd (the first road you come to).
Clean. Friendly. Elegant. Cheap. GREAT morning breadpudding/French toast.
I ask personally that you NOT patronize the Rockwood Trail House. When I came into town one evening at 8 pm, you turned me away (which is OK). When asked if there were other B&B's or motels around, he told me "NO." (There is one 200 feet up the road, jerk!).
I had planned to camp that night, but a thunderstorm was coming in.
When I stopped in his shop the next morning to ask about it, he was gruff and hostile.
Rockwood Trail House. Here's your recommendation to the Pittsburgh Bike Community, dude! It's true. It's accurate! You earned it! I sure hope you like it!
In Frostburg, the Trail Inn has very nice clean rooms. Their food is dreadful and you should climb the hill to town for dinner. (although the breakfast with the room is OK)
If you get a chance to get the proprietor to talk about the history of the trail, do it! Wonderful Raconteur.
The Holliday Inn in Cumberland is really bike friendly and they have a swimming pool.
There *IS* a B&B in Little Orleans and One in PawPaw WV, but neither of them made it to the Trail Book. The one in Little Orleans has been recommend to me by reliable sources, although I haven't stayed there. The one in Paw Paw is OK at best (cheap thought).
In Hancock, I stayed at teh 1828 B&B. I got in late and left early and dont' recall much. There were aquaintences of mine staying there, so that overwhelmed other impressions.
Weaver's Diner and Bakery in Hancock is really good. (Try their Blueberry pie. Trust me.) It might be worthwhile to stay at the Motel (cheap) and eat breakfast there.
Once, in Hancock, after gorging myself with Cheerios peanut butter and banannas in my hotel room, I discovered they ahd asome civic pancake "all-you-can-eat" breakfast in the park that morning. Shame I missed it.
There was an OK B&B in Williamsport directly accross from the wonderful Desert Roase Cafe, but Google isn't helping me find the name.
If there is still the detour, I say skip that sectionof teh trail and ride from Williams prot on Speilman Rd (Rt 63), Bakersville Rd, and Sharpseville Pike (Rt 65) through the ghost-filled Antietam Battlefield. Plenty of (fairly pricey) B&B's in Shaprsburgh, then Harper's Ferry Rd out of town the next morning.
The Norris House in Leesburg, VA was really nice in every respect, lovely room, great food. - but a bit pricey. To get there you pay $1 for a ferry across the Potomac that is cool and a few miles of trafficy road.
There is a paved rail-trail from Leesburg to DC- but you miss Great Falls on the Potomac. It it's been raining, it's worth it for sure.
Hope this all helps.