I've used the free night quite a bit. What's nice about it, that's different to other loyalty programs, is that you can choose from all hotels in their inventory. You're not confined to only Starwood, Hilton, or the others out there. The $400 cap provides an adequate allowance to choose some really nice properties, if you choose well. You will have to pay resort fees and usually a small processing fee. I just booked a 5 star hotel in Athens, Greece, for $35. I'm pretty happy with it.