8 Deal Breakers to Consider Before Entering to Win Trip Prizes

Do You Really Want to Win That Trip?

Lost female tourist on a desert island
••• Buena Vista Images / Getty Images

Winning a free trip sounds like a dream come true. After all, we could all use a getaway, am I right? And vacation prizes can be wonderful, giving you the chance to enjoy once-in-a-lifetime experiences, relaxing getaways, international travel, and much more.

But before you start entering every vacation giveaway in sight, stop to take a moment to think about whether the prize is right for you. You'll waste your time and the sweepstakes' sponsors' if you're trying to win trips that won't really make you happy.

Here are some common deal breakers to consider before you start entering trip giveaways.

Deal Breaker #1: The Prize Is Free, But the Trip Isn't, Quite

It's true that sweepstakes give away free prizes, but that doesn't mean you won't end up paying something for your vacation. Some expenses commonly associated with trip prizes:

  • Transportation to/from the airport and hotel.
  • Meals while you are on the trip.
  • Transportation around the city/country you're visiting.
  • Rental car and gas.
  • Tips for housekeeping, taxis, etc.
  • Souvenirs.
  • Sightseeing expenses like entrance fees and tours.
  • Phone calls home.
  • Luggage, new clothes, or other necessities for the trip.
  • Passport and visa fees, if you win a trip abroad.
  • Travel insurance.
  • Lost wages, if you need to take unpaid leave from work.
  • Taxes you pay on sweepstakes prizes.

So before you enter to win a vacation, be sure you check out exactly what's covered by reading the sweepstakes rules. Many vacation prizes pay for some or all of these costs, while others give you discretionary cash to cover expenses. Before you submit the entry form, decide whether you are willing and able to pay for any uncovered costs.

Deal Breaker #2: How Much Time Do You Have to Prepare If You Win?

Some trip sweepstakes leave only a few days between the time the winner is notified and the day you have to leave on your trip. Read the rules to see how much notice you'll receive if you win.

If the preparation time is short, make sure you have a passport on hand and can get the time off work on short notice. If not, you might want to skip the sweepstakes.

Deal Breaker #3: You Might Not Be Able to Bring Your Kids on Your Trip

Some trip sweepstakes have no problem (or even encourage) you to bring your child as a guest. Others, however, have strict age restrictions for the winner and all guests. Make sure you check the rules before entering if you want to bring minor guests with you if you win.

You may also win a trip that doesn't include enough guests to cover your entire family. Sometimes, you'll be able to pay to bring extra guests  along with you. In other situations, it might not be possible to bring any extra people with you.

Deal Breaker #4: Airfare and Hotel Costs Aren't Covered

Most trip sweepstakes include airfare and lodging in their prize, but some don't. Be sure to check carefully if you don't want to end up being responsible for part of the trip's expenses yourself. Some experiences might be worth the extra money, but some won't be.

In addition, some trip sweepstakes will remove the airfare portion of the prize if you live within a certain number of miles of the destination. Sometimes, they'll substitute a rental car or limo transportation to the hotel or event, but not always. In these cases, if you live nearby you might need to travel a hundred miles or more on your own, without being reimbursed for your costs, to get to your destination.

Deal Beaker #5: The Taxes You'll Need to Pay for Your Trip Are Too High

One of the drawbacks of winning sweepstakes is that US residents need to pay taxes on their prizes. Vacation prizes have a lot of wiggle room when it comes to the value of the various things included in the trip.

Remember that the ARV is called the "average" retail value for a reason. The actual, taxable prize value will be determined after the trip has been taken.

For this reason, it's a good idea to document the lowest prices you can find for your trip. You may be able to dispute the ARV on your taxes and pay less.

The sponsor may also be able to work with you to reduce the total cost of your vacation. By turning down extra activities or other features that you don't really want or taking one guest with you instead of three, you could reduce your tax cost.

Deal Breaker #6: You're Banking on TakingCash Instead of a Trip

Many people say that if they win a vacation prize, they will simply opt for the cash option instead of traveling. Which is fine, if a cash option is included in the prize, but trip sweepstakes don't have to offer a cash alternative. Read the rules, and if a cash alternative is not specifically offered, don't assume you will be able to talk the sponsor into giving you one.

Deal Breaker #7: You're Planning on Giving Away Your Trip

Some people think that if they win a trip that they don't want to use themselves, they could always give it to a friend or loved one. However, this is rarely the case.

Most trip sweepstakes require that the winner is one of the travelers and that the winner and all guests travel on the same itinerary.

There are some exceptions; a gift card to a travel site or airline might be usable by people other than the winner, but be sure to read the rules carefully to be sure that the trip is transferable if you don't want to go yourself.

Deal Breaker #8: Your Guests Might Not Get All the Goodies

Some trip sweepstakes offer special extras like shopping sprees, photo shoots, spending cash, and admission to special events or attractions. Sometimes your guest or guests will be invited to go along with you on all of the bonus experiences, but sometimes only the winner will receive those portions of the prize.

To make sure that the guests aren't disappointed, be sure to read the rules carefully so you'll know what their portion of the trip sweepstakes win will include.


Vacation prizes give you the opportunity to expand your horizons and to build memories you will never forget. But taking the time to enter only the vacation sweepstakes you really want to win will avoid bad experiences.

While you're at it, here are some other things to watch out for while you're reading sweepstakes rules.