Well, it depends how big you want to go. Some people who hate winter (yet oddly choose to live in cold climates) arrange their schedules to take off as much as time as possible in December and January. Whether you can engineer your lifestyle to go a month or longer away from your "regular" life around Christmas, or you can only get away for a few days, make your life easier and follow these steps when planning for a Christmas vacation. (To learn about travel insurance for you winter getaway, read The Basics Of Travel Insurance.)
TUTORIAL: Credit Cards
Here are some strategies you might not have thought of.
Plan Several Vacations at Once
Planning a vacation, or even a simple business trip, is far more complicated now than it was in the prehistoric area (before Orbitz, Expedia, Travelocity, etc.) You can compare hotels, rank them by price, rank them by amenity level, rank them by distance from the airport, cross-reference them with reviews on TripAdvisor and read the reviews of those reviews. Hopefully, you'll still be in the mood for a vacation if you don't succumb to paralysis by analysis first.
It's easy to burn hours doing this, but if booking a trip is a necessary evil, minimize the duration of the discomfort and book multiple years' worth at once. This makes sense psychologically, too. Next November, the idea of going to Namibia a mere month later might sound grandiose and unfeasible. If you plan an exotic trip 13 months ahead of time, you might be surprised at how achievable it can be. (For related reading, see Travel Tips For Keeping You And Your Money Safe.)
There's an implicit understanding among some friends and family members, usually the latter, that you're supposed to return home bearing trinkets which indicate that you visited the destination in question. You don't. This is an outdated and expensive custom made largely irrelevant by advances in international commerce. When you can get Australian snow globes on eBay and Brazilian t-shirts down the street, the only purpose to buying international junk is to test the stowing capacity of your luggage. Tell Grandma she's going to get digital photos, and she's going to like them.
Everything Has a Price
Yes, red-eyes and other inconvenient flights are cheap. There's a reason for that. Such flights are for insomniacs and the very frugal. Do yourself a favor, pay the extra $40 and leave in the late morning. How much is a good night's sleep worth to you, anyway? You're presumably well-rested and conscious while reading this, so you're probably not all that committed to answering the question right now. Let's try it again when your alarm goes off at 3:17 a.m. in order for you to catch your 5 a.m. flight, and someone offers you four more hours of blissful sleep. In that situation, some people would gladly cough up the price of an airline ticket and then some.
Besides, getting wherever it is you're going a few hours earlier isn't worth it if you're irritable from the lost sleep. Vacations are supposed to be for avoiding stress, not enhancing it. (For cost saving traveling tips, see Globetrotting On A Budget.)
Flying Isn't the Only Mode of Transportation
Unless you're crossing an ocean, try the train. It's not exactly news that trains can be a destination unto themselves, and the kid who doesn't get excited at the prospect of riding one has yet to be born. Yes, it's slower than flying, but on the other hand you don't have to walk through endless security gates to ride the train. You don't have to remove your shoes or your dignity. You can go to the bathroom whenever you feel like it. There are power outlets and the worst meal served on trains is generally better than the standard coach food on any airline. (For related reading, see Save On Planes, Trains And Automobiles.)
Be Aware of Credit Card Charges
It seems that some people think that there's a special currency called "vacation dollars," which spend more easily than their everyday counterparts. If you were prudent enough not to run a balance the rest of the year, don't let Christmas be the time that you go off your fiscal diet and start to loosen your figurative belt. If you were running the balance the rest of the year, you should pay it off in its entirety before indulging yourself with vacations anyway. (For more on using credit cards while traveling, read 4 Tips For Using Credit Cards Overseas.)
The Bottom Line
Though the perfect vacation is different for everyone, these tips will lead to a more comfortable and, hopefully, more affordable vacation.