Avoid nonstop flights. To find a less expensive airfare, search flights (or request flights) with one or more stops if you can afford the time. When using travel websites for booking, refrain from clicking "nonstop flights only" or search all flights and compare prices, recommends Tom Parsons, founder of bestfares.com.
[See: 10 Ways to Avoid Airline Fees.]
Ask for transfers. Traveling to and from the hotel tacks costs onto your midwinter vacation, so inquire when booking by telephone or through a travel agent if the hotel or resort has a free shuttle between the airport and the hotel. Plan ahead for this, as it will make your trip smoother and cheaper.
Find free breakfast or happy hours. No matter where you stay, it's always worth finding out which hotels include breakfast of some kind with your room. Even if it's a continental breakfast, you'll still save.
Ask for a refrigerator. Instead of eating in restaurants, aim for at least one meal each day in your room or on your balcony or patio. Research ahead where you can shop or, if you can handle the challenges, bring some nonperishable food with you.
Timing a midwinter vacation can save you money on airfare and hotels, so plan your trip sometime after Jan. 4 and before President's Day weekend. Think through the details, including meals and transportation to and from the airport before you go. You'll spend less and enjoy the trip more.