I have stayed at a lot of posh hotels on other peoples dime - work things, conferences, trade shows. Not as much recently as those things have died out, but in the past. Places like the Hotel Del Coronado. Yes, very nice place, but in the end it was just a hotel room. I wouldn't make a huge effort to go back even if it was cheap, which it was not. I think a lot of it is so you can tell people you have been - like paying $1000 for a certain sneaker - its the status symbol not the product.
Possibly one exception being the Windsor Court Hotel in New Orleans. Every tiny detail is perfect, from the room to the bartender to the mixed drinks. Reminds me of the old South which is slowly going away. Pay for a Premium level floor which gives you access to the top floor lounge whose finger food offering at high tea is "complimentary" and not to miss, and I am not a tea kinda guy.
The only hotel I have interest in is maybe the Breakers for its historical significance. Maybe I'll just stop in for coffee some day.