Do you think Toledo (and the Toledo Hilton?) are worth a trip of their own? Or is it worth staying at MAD (and likely pay less/use fewer points) and make it a day trip?
Toledo is absolutely worth a trip! It is a beautiful city. I don't know where the Hilton is in Toledo, but I was able to stay in a beautiful little pensione (sorry dont recall the name but there are tons of them) for 80 EUR a night including breakfast for a double room. I would personally stay in the old centre- and I would not miss Toledo as it is worth the trip.