Hi Tara,
Thanks for stopping by the Disney Parks Moms Panel for assistance with your vacation planning!
If you have your heart set on a specific
Disney Resort hotel or have travel dates in mind that aren't flexible, I would recommend booking your reservation now. The Walt Disney World Resort is extremely popular and advanced planning is the key to securing your preferred resort. In order to hold a "Room Only" reservation, you only need to pay a deposit equal to the first nights room and tax. You can always convert this "Room Only" reservation into a
Magic Your Way Vacation Package later. These packages include your room as well as park passes. You can opt to add the Disney Dining Plan as well. You are correct that Disney does offer "Free Dining" several times during the year. If you have already booked your reservation and you see one of these offers come out, you simply need to call a Disney Travel Planner and request that they modify your existing reservation to include the "Free Dining" offer. Alternatively, you can simply book the special offer, and then cancel your existing Room Only reservation as long as you within the cancellation period. You will want to keep in mind that the number of packages available at the various resorts are limited with special offers. So call as soon as you see one released for the time frame that you are traveling. If your preferred resort isn't available, you may want to consider switching to a different resort in order to take advantage of the "Free Dining" offer. I recommend that you not pay off your vacation in full until 45-days prior to arrival as this will make it easier for you to modify your reservation if need be.
Wishing you magical memories,
Kaylene