It does matter when from what I've read December is historically very busy on property. If we had an owner cancel on us (however unlikely) that means our options (outside of DVC) to recover would be severely limited and we would likely be spending far more than we could have potentially saved. Make sense? I am also aware of the booking windows for DVC- information on that is pretty easy to find online. The broker sites make it clear as well from the upcharge for booking out further than seven months in advance.It is not about crowd but timing and demand. DVC works best planned more than 7 months out. Fall is DVC high demand season, which is independent of crowds.