It used to be that procrastination didn’t pay when it came to travel. But with the explosion of Internet travel sites, sometimes waiting to book until the last moment will net you a better deal than meticulous long-range planning. Here are some tips to help you book that much needed vacation for the upcoming holiday season. 

Package deals
Flights tend to be marked up close to the departure date to capitalize on business travel, so book both flight, hotel and/or car rental as a package. The flight will be considerably cheaper than as a stand-alone purchase.

Check Lastminute.com for package vacations of either flight plus hotel or flight plus car that can be booked up to 3 days in advance to both domestic and international destinations. For price comparison, your search will also bring up alternative dates and more attractively priced proximate destinations. You may choose from a range of flight options, hotels and car rental services, with the final price tag clearly marked. A sidebar provides helpful information on your chosen destination.

Online booking services
All the major travel services websites feature last minute domestic and Caribbean deals. Orbitz and Expedia offer last minute deals on hotels, flights, cars, cruises and package vacations; Orbitz also offers sports, music and theater tickets.

Use Hotwire to browse last minute deals by theme (4-star hotels, golf) if you don’t have a specific vacation spot in mind, or by destination. Hotwire also allows you to blind-book car rentals or hotel rooms just days in advance, when businesses drop their prices, sometimes drastically, for their unused inventory. Though you are informed of the car’s pick-up location, mileage restrictions and size, or the hotel’s neighborhood and star rating, you don’t find out with which business you’ve booked until payment.

Cruises
Especially if you live near a port, cruises are a bargain hunter’s delight. Ships that will sail in a few days are eager to fill their empty cabins. And because they repeatedly make the same trip, there are generally lots of dates to choose from. Check out sites like CruiseDeals.com, CruisesOnly and LastMinuteCruises.com for some incredible markdowns on cruises departing as soon as 2 days from booking.

Flying
Airfarewatchdog.com offers an easy way to find short-lived deals and cheap tickets. The site doesn’t book the flights for you, but directs you to the website that is offering the discounted ticket. The site also includes discount airlines, like Southwest, and smaller airlines that are not featured on Orbitz or Expedia. Promo codes are provided so you get the additional discount when you book. Not all flights are "last minute." Many require at least a 14-day advance purchase.

Not only are fares higher on peak travel days, but now most major U.S. carriers (except for Southwest Airlines and JetBlue) have instituted a holiday surcharge fee of $20 for those most-traveled days of the year. To avoid the surcharge, and for cheaper tickets in general, plan to fly on the actual holiday itself. See United Airline’s calendar for what days to fly to get the best fares around the holidays. Also, be aware that most airlines are charging additional fees for reservations made over the phone or at ticket counters. Most websites cannot process tickets less than 48 hours prior to departure, so for the literal last minute traveler, expect to pay more.

Comparison shop all accessible airports. Sometimes the nearest airport is not the cheapest.

Online bidding
For those who like to bargain, Skyauction.com offers everything from Broadway shows to flights to vacation packages. They tell you what the minimum bid is, and you go from there. After you have made your bid, the item’s page will display the current highest bid and the time remaining until bids are no longer accepted. Each item has a comprehensive description, including dates of availability, restrictions and additional charges that may be incurred. Many of the items are available for immediate departures. The site also offers discounted travel which you can buy without bidding.

In the same vein, Priceline allows you to blind-bid on flights, hotels and car rentals. The airline, hotel or rental agency is not revealed until the bid is accepted. Pertinent information, like location, star-ratings and car-size, is provided to help you make your bid. Generally, bids are responded to in less than 5 minutes. If your bid fails, you can always try again.

Other tips
Travel to an off-peak destination—winter holiday travel trends towards warm weather destinations, leaving other destinations looking to fill their empty hotel rooms. Hotel rates in Europe are considerably cheaper from November to April. Also, if you travel somewhere that doesn’t celebrate Thanksgiving or Christmas, you may avoid both holiday prices and holiday crowds. For weekend travel, go to cities that get a lot of business travelers. Conversely, travel to big weekend destinations during weekdays.

Keep it close to home—that way you don’t have to pay the hiked-up fares charged by the airlines. Scour the local paper’s travel section for B&Bs or inns that are offering great holiday deals, or call to see if rates have dropped for upcoming weekends. Do keep in mind, though, that the Wednesday before Thanksgiving is one of the busiest days on the road.