That's a good question, and I can't recall if I've ever seen it offered in May. But then I'm not usually close to going then.
However, May often sees better discounts than "free dining", with room-only discounts and room/ticket discounts. "Free dining" requires paying rack rates for the rooms. If you wish to stay in a deluxe resort, there is very little chance that saves you money in the bottom line, versus getting a room or package discount and paying for dining out of pocket.
I had a PIN Code for free dining this year, we used it in June but I want to say it was good in May as well. For our family of 6 it saved us a ton, especially with 2 kids counting as adults now! However like the PP said above there are usually great discounts and unless you have a lot of adults (over 10) in your vacation free dining is not actually always the best deal.
We always go in May and I never realized there was free dining via pin code or otherwise. Boy, I would love to get one of those for our May 2011 trip!!
We were planning to arrive May 26 so I just booked the package for May 27-June 2 (we were already planning to leave June 2) and we'll do room only for May 26. I think I'll wait a month or two before booking that room only.... the call center has to be crazy right now.
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