Hi Tammy!
Thanks for visiting the Moms Panel with your great question.
There's no real way to know what fantastic offer Disney will offer next or what resorts or time periods it may cover. Sometimes, fantastic offers are made available as 'last minute' deals, while other times, the offers are available far in advance for 'off peak travel times.' This past year, Free Dining was offered for latter half of August and similar dates in 2011.
What I always recommend is to book the Resort and Package you're comfortable with in terms of price and date, and to reserve as far in advance as you can. That way, if a special offer doesn't become available for your travel dates, you'll still enjoy the great vacation you had planned and budgeted for.
Then, keep an eye on the Walt Disney World website's '
Special Offers' section often!
If a new offer comes out, call (407) 939-7675 and mention that you have an existing reservation and would like to switch to the "such and such" offer. The Cast Member will advise you of availability under the offer and can even help you compare to determine what's best for you! The offer may vary by resort level in terms of which properties have availability, what percentage discount is available or what 'free' add-ons such as dining are being offered.
I hope you'll write me back soon with any additional questions you may have.
Wishing you a Magical time planning your next Walt Disney World vacation Tammy!
Kirsten