my experience is that if you can find a parking garage with a charger that in close by to wherever you'll be staying that it more than likely would be less expensive to self park and walk a bit than it would be to utilize the hotel's parking. for example on a recent visit to chicago the hotel parking was almost $75 per night and a block away I could park for $52 a night and use the chargepoint L2 units at no costs. the answer to your question is a between cost or convenience, are you willing to walk a block or two to save $20 or do want to pull up to the door and let the valet do the walking?
for me I'd rather not allow someone else to park the car and to plug it in properly, I don't mind the time lost to parking it myself and I am happy saving $20+, everyone has different tolerances