I think how easy/hard the road trip will be depends on your pup. Trixie has been a great traveler, she's been on lots of long road trips (and one long plane trip overseas). I just make sure we have lots of potty breaks (every two hours or so), have fresh water available (or give it to her by syringe), food and nutrical in case she doesn't want to eat.
You'll be surprised how easy it is to find a hotel that allows pets. Just go to
www.petfriendly.com and alsmost every city has a few. Mostly largers chains like Holiday Inn, Super8 etc.
If I were you, I'd take her.