The best hotel has been a Hilton so far. I was staying with family and it was newly converted hotel from a long term stay and sheesh...it was plush with multiple bedrooms, giant pillows, a fireplace with a suspended chimney, a giant bathroom with walk-in shower and a hot tub. I've definitely day dreamed about driving 9 hours to that place to refresh my memory so I can try to mimic that on a floor of my next house, whenever that happens.
In my cross country trip I stayed at a few pretty nice places, mostly out west it was either the quaint town and the western accents on the design of the hotel and/or the view.
On the terrible end it was definitely a Jersey shore Motel when I was a kid. Fire escape style stairs, on the facade of the building, Water stains on the ceiling, musty, the inescapable stench of cigarette smoke everywhere. of course there had to be one beer belly guy with a speedo. It was horrible. I still enjoyed the beach, the boardwalk, restaurants, arcades etc. I just tried to stay away from the hotel except to sleep as much as possible.