Hi JenB,
We (my husband and I) book our accommodation first, as long as we have a place to lay our heads we are set. We often wait until after September (we normally travel in late December to mid January) as the prices seems to go down a bit, this is historically what we have seen.
Right now for us, prices are up and we're hoping that they will go down some.
Hope this helps.
Peace,
Brynn - Islander