Ideally, I start doing my Christmas cookie baking at the end of October. I usually make around 20 different varieties of cookies, so I try to split it up, doing a few recipes every weekend.
I store the cookies in individual Rubbermaid containers with waxed paper between the layers, and then store them in the freezer. If the cookie needs to be frosted or topped with powdered sugar, I leave it off and frost or sprinkle after the cookies are thawed and I'm ready to make the cookie platters. And I save my most delicate cookies for the last baking weekend so that they don't have to be frozen.
I also start shopping at Dollar Tree around October to catch the Christmas plates and containers as soon as they come in. I got the cutest Santa and Snowman plates last year for $1 each, which was great for making up my cookie platters. I make platters for my close neighbors, family, friends and the staff at my kids' school (about 15 platters in all), so it helps not to have to do it all at one time.
I hope that helps.