I am usually booked far out, at least two months. I get nervous if I have open weekends a month out and start lowering prices little by little. My high season (May-August) fills up by end of February.
@Emilia42 while this should theoretically be true about having too low prices if booked far out, I am wondering why I rarely get booked at my rates if I happen to have an open window in a month out range. I am thinking because I rent out a whole house and usually have bigger groups (girl trips, reunions, etc), those just happen to plan in advance.