So What's Your Best Strategy?
Road-Trip: Pump the breaks on booking early, unless visiting an exceptionally popular destination where hotel options will be limited. Watch rates dip as your desired check-in date approaches, then strike when it feels right.
Just A Flight: Confirm your travel plans now, you're in the optimal booking window of 60-70 days prior to departure.
Flight + Hotel: Decide how much flexibility you have within your itinerary. Book your flight now. Monitor hotel prices and availability as your trip approaches. If you're taking an extended trip over the last week of the year, consider booking a room in advance for the first half, then making a second reservation mid trip in order to save the most money.