If you're gonna drive you can probably wait until just a few days before your departure to pick an area with a good number of trails open. Going closer to Xmas might give you a chance for slightly better conditions. There should be plenty of lodging available as long as you're returning home by about Dec 23. As you know Killington is pretty good about opening terrain early. A laundry list of other good early snowmakers might be Okemo & Mt. Snow in southern VT, and Sugarbush & Stowe in northern VT; Quebec (Mt. Ste Anne & Le Massif, or in different area Mt Tremblant) is an interesting suggestion, longer drive, but might be worth it if conditions are significantly better than New England; Bretton Woods, Loon, or Waterville Valley might be pretty aggressive about early snowmaking in the state of New Hampshire; Sunday River might be good for early season in Maine; Gore and Whiteface might be a cool pairing for a couple days each in NY state although they don't have as strong a snowmaking reputation as others mentioned.
The world is your oyster, just follow the weather, fill the car with gas, and be ready to accept only 50% trail openings, which is probably better than what you'd get in western PA at that time.