I forgot to mention it also depends on WHEN you're booking the flight/hotel room for, if it's during high season 5-6 months in advance is critical for best pricing.... Off season it's usually the complete opposite and booking that far out is bound to cost you a lot more.

I generally also do a stopover in Florida instead of a direct flight from DC, as it saves money and I don't mind being in an airport terminal for a few hours, flying direct can be a LOT more expensive and a layover on the way back lets me get caught up on work.

I wish I had enough miles saved up for the flight, generally airline tickets are "free" thanks to putting everything on a work credit card.