I used to prefer the first full week of December. We ate off-resort and stayed at a hotel outside the gate because low demand meant dirt cheap room rates, but now the Pop Warner Super Bowl and National Cheer and Dance Championships are usually that week so switched to the week following Thanksgiving which conveniently offers free dining even at the cheapest resort on-site, All-Star Music, which we upgrade from the quick service dining plan to regular dining then eat breakfast we bring in our room saving those credits for snacks in parks. Free dining comes with opportunity costs like losing the fall room discount and being forced to buy the park hopper option, but if you want to eat on resort it's still cheaper. The weather is usually spring like and hurricane season is at a close. The three of us are paying $2,517 for 6 nights/7 days on resort with park hopper tickets and free regular dining including meals at Akershus, BOG, Cinderella's Royal Table, 'Ohana, Mama Melrose, & Sanaa so two people should be able to do it for under $2,000. We could save hundreds by staying and mostly eating off-site, but not if we paid out of pocket for character meals for our daughter. MK closes early some days for the Christmas party, but it's easy to schedule around and we enjoy the Christmas decorations. If flexible on dates and staying off site I suggest looking for the best room rates with no cancellation charge. That way you can keep looking and booking better deals until closer to departure.