Hi Lisa,
Welcome back to the Disney Parks Moms Panel! I love your commitment to savings. We always have a budget when planning our trips to the Walt Disney World Resort!
In my experience, I have seen Free Dining offers available at different times during the year so there is always a chance that another Free Dining offer will appear. I have seen it
offered for dates in late August in the past but there is no guarantee that it would be offered at that same time in future years. Having said that, I always check other
Special Offers against that of Free Dining offers. The Free Dining offer has not always been the best price. When you do the price comparison, be sure to check the Free Dining offer against another special offer with the same type of park tickets and with a dining plan added. Also, be sure to look at the special offers for Canadian guests.
I do have one additional suggestion. We typically make our reservations with the current special offers and do not wait for a particular special offer to come available because we prefer to get a certain resort and room type. If we wait, our preferred room type might not be available when Free Dining appears. If a special offer appears and is applicable to your resort and room type, I suggest that you contact your travel agent or the Walt Disney World Resort to see if a cast member can apply it to your reservation. I have been able to do that in the past. Just know that special offers cannot always be applied to existing reservations.
Lisa, I am sending pixie dust your way as you try to the find the best deal for your family!
Magic, memories and Minnie Mouse hugs,
Donyell