We usually go then end of January. I have looked at my past 3 invoices and I booked end of July / Early August. Now that was booking with free dining...not a room discount.
But keep in mind if you are waiting for free dining... there was no free dining offered this January / February...so there no guarentee it will come back for next year either.
We are hoping it does though! We've been spoiled by it for the past sseveral years.
We went in February this year and the discount was offered around October 9, 2012. There wasn't any free dining in the offer. We were really hoping for that, too.
This was the promo for this past Jan/Feb...Play/Stay/Dine
Package With Disney Dining Plan at Select Disney Moderate, Disney Deluxe, and Disney Deluxe Villa Resorts: For example, purchase this 5-night/6-day Magic Your Way package for a family of 4 that includes tickets, the Disney Dining Plan and a standard room at a Disney Moderate Resort valid for stays most nights January 2 January 9, 2013, January 13 January 17, 2013, and January 21 February 13, 2013 for just $2,429. That's a savings of $633!
Package With Disney Quick-Service Dining Plan at Select Disney Value Resorts: For example, purchase this 5-night/6-day Magic Your Way package for a family of 4 that includes tickets, a Disney Quick-Service Dining Plan and a standard room at a Disney Value Resort valid for stays most nights January 2 January 9, 2013, January 13 January 17, 2013, and January 21 February 13, 2013 for just $1,967. That's a savings of $406!
Total package price based on 2 adults, one junior and one child. The number of rooms allocated for this offer is limited. Savings based on non-discounted price for the same package. Tickets valid for one theme park per day and must be used within 14 days of first use. See Important Details.