Jody has excellent advice. Once you figure out your flights get your reservations in order. I usually put everything together and reserve rooms about 5-6 months in advance...and then reconfirm closer to my departure date. 8-9 months in advance might even be safer, though some establishments won't allow that.
This most recent trip I shot myself in the foot by forgetting to book rooms well ahead of time. I browsed accommodation listings 5 months in advance and began to seek out reservations 4 months out, in the meantime a convention was booked into town and my main and 7 alternate choices were booked up. At three months out I've only recently managed to track down a room.
Finding a room closer to your departure date might be easier for one person, however; I'm usually trying to book for two to four making the job a bit more difficult.