We did a Texas to Massachusetts trip a couple months ago in the Model Y with the family and honestly I never based anything on hotel chargers. I just picked the hotel and checked PlugShare for fast chargers nearby. Only actively waited for a charger three times the whole way. A destination charger is a bonus but I wouldn't trust it as the plan.
We did get stuck once at home in the winter when a couple of public chargers were down and snow was blocking an EVgo. Ended up paying $0.53/kWh at a dealer just to get home, so I'm wary of anything that's only one stall.