These days, you're better off finding a way to get "status" from a chain so you can cancel without penalty and book a bunch of rooms. Our last road trip, I booked 4 rooms over 300 miles and cancelled in the afternoon before stopping in.
It all depends on the approach. Instead of saying "do you have any rooms available?" you could just say "I only have $AMOUNT and quite frankly I'd rather stay here than at my old Uncle's place down the road" (or a variation of which indicates 'price does not matter'. [1]
Disclosure: I am somewhat of a paid professional negotiator so techniques like this may not work if not done properly or in every context.
[1] In another business you'd be surprised at how many people simply say 'can you do any better' (which means 'you have the sale') rather even 'wow that's to high... a competitor will do it for $AMOUNT can you match that?' Edit: Emphasis on a convincing use of 'wow!'.
>Our last road trip, I booked 4 rooms over 300 miles and cancelled in the afternoon before stopping in. Oh, you're /that/ guy.
I'm following the rules.
Its obnoxious behavior, but what am I supposed to do?
If I arrive late, the hotel will happily give my room to the platinum member who rolls in or some random person, and leave my family stuck in the room designed for wheelchair bound chain smokers with pets suffering from shedding disorders.
If I book same day, the $99 motel turns into a $139 hotel. If I just show up, I roll the dice.
I also limit myself to newer nice motels.