While winning a free vacation, like any other contest of chance, is mostly a matter of luck, there are ways you can increase your chances of winning that fabulous trip to the tropics or the slopes. First, you must enter. Sounds easy, right? Unfortunately, many people don't take this first step and, thus, never have a chance to win. Second, you have to find the contests. It will take some diligence on your part, but there are ways to find get yourself a vacation for no cost.
Sign up for email newsletters at travel information websites such as Frommers.com and Concierge.com. Frommers has contests about once a month, with many prizes being vacations for two. For instance in July 2010, the prize was a trip for two to Ireland. Concierge.com has regular contests. A recent contest was for a $25,000 dream trip to anywhere in the world. Enter as often as possible. A contest often will ask you to submit email addresses of friends and family to increase your chances of winning a contest.
Look through travel websites and newsletters for contests being offered by advertisers. Many travel companies offer their own contests not related to the site hosting the advertisement. For instance, on a recent email Frommer's newsletter, a company called Nile Guide was holding a contest to win a trip for Aruba.
Check travel sites like Travelocity.com, Orbitz.com, Cheapoair.com and Expedia.com for contests. Travel sites often host contests to lure customers to their sites.
Read travel magazines and the travel section of your newspaper, and specifically look through the advertisements for contests. Advertisers often host contests so that they can capture customer information for their databases.
Enter contests as many times as you can. Send a reminder to yourself to re-enter contests that allow you to enter once a day so you won't forget to submit your entries.
Look for writing contests in magazines such as Budget Travel. The prize for winning Budget Travel's funny True Stories section is often a vacation.
Watch the Travel Channel or travel-related shows like CBS's "Amazing Race." Travel-related television shows often have promotional contests during the season to lure viewers. The Travel Channel website also holds contests for trips.
Sign up for timeshare sales pitches. If you are willing to sit through several hours of sales pitches, some timeshare resorts will give you a a few days at one of their resorts as a prize.
Work for a company that offers vacations as incentives. Some companies, such as Computer Associates, will offer their salespeople paid vacations if they meet their sales goals.
Collect miles on airplane trips, credit-card usage, and hotel miles every time you stay at a hotel to earn free airline trips, hotel stays and car rentals. While this is technically not winning a vacation, it is a way of getting a vacation for free.
Organize a group trip. Some travel companies and cruise lines will give a group's organizer a free trip or cruise. A group can be a family reunion or just people you know. Consult with a cruise line or travel agency to see if they offer this incentive--and what size your group needs to be to qualify for a free trip, as it varies from business to business.