I have to admit I have recently been disappointed with DVC.
I have tried to book accommodation several times at my home resort for dates that are not at peak times and have found no availability, even though I am within the 11 month window and the accommodation had not been opened up to all DVC members (7 month window).
I have been a member for over 10 years and have only had this problem recently.
Whats going on!!
I really dont think you should have to ring up every day to book each day as it opens up.
Own at BCVs and SSR and we have only had to waitlist once in 11 trips. That was at new years when I forgot and booked several days later that I should have ( waitlist came through 1 month later). I normally book somewhere between 9 and 10 months out and yes this frequently includes food and wine festival time. On one occasion we booked 9 days out for a last minute trip.
I think it depends largely on when you want to go and, depending on your resort, the room view/category. If you really, really have to get the reservation you want, you should book day by day when your window opens up, just to be certain.
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