8 Deal Breakers to Consider Before Entering to Win Trip Prizes

Do You Really Want to Win That Trip?

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Winning a free trip sounds like a dream come true. After all, who doesn't want a free vacation? And it's true that trip 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, take a moment to think about whether the prize is right for you. There are some good reasons to be picky about the trip sweepstakes you enter.

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

The Prize Is Free, But the Trip Isn't, Quite

You may win a free trip, but that doesn't mean you won't end up paying something. Even when airfare, hotel, and entertainment is covered, you may end up with other costs you have to pay out of pocket. Some common expenses with trip prizes include:

  • Transportation to/from the airport and hotel.
  • Meals while you're away.
  • Transportation around the city/country you're visiting.
  • Rental car and gas.
  • Tips for housekeeping, taxis, tour guides etc.
  • Souvenirs.
  • Sightseeing expenses like entrance fees and tours.
  • Phone calls home.
  • Luggage, new clothes, and other necessities for the trip.
  • Passport and visa fees, if you win a trip abroad.
  • Travel insurance.
  • Medical costs like vaccines, which are required for some destinations.
  • Lost wages, if you need to take unpaid leave from work.
  • House- or pet sitting costs.
  • Taxes.

Before you enter to win a vacation, be sure to check out what's included 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.

Then, before you submit the entry form, decide whether you are willing and able to pay for any uncovered costs.

You Don't Have Time to Prepare for Your Trip

Some trip sweepstakes give you only a few days between the time you're notified and the day you have to leave on your trip. Will you be able to travel on a moment's notice, if that's the case?

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.

You Can't Bring Your Kids (or Your Spouse) 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 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.

Will you be able to go if you have to leave a spouse or children behind? If not, this might not be a giveaway for you.

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.

If some of the standard travel costs aren't covered, you need to decide whether it's worth paying for them yourself.

Additionally, some trip sweepstakes won't cover the airfare portion of the prize if you live within a certain distance from the destination. Sometimes, they'll substitute a rental car or limo transportation to the hotel or event, but not always

In these cases, you might need to travel a hundred miles or more on your own, without being reimbursed for your costs. Is the rest of the trip worth it?

The Taxes on Your Trip Are Too High

One of the drawbacks of winning sweepstakes is that US residents need to pay taxes on their prizes. If you win a big trip, like a pampering vacation with an ARV of $10,000, the taxes you'll end up paying can be pretty hefty.

The good news is that 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 you've taken the trip.

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, features that you don't really want, or bringing fewer guests with you, you could reduce your tax cost.

You're Banking on Taking Cash 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 isn't explicitly offered, don't assume you'll be able to talk the sponsor into giving you one.

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 specify that the winner must be 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, for example.

But be sure to read the rules carefully to be sure that the trip is transferable if you don't want to go yourself.

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. Your guest or guests might 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'll never forget. But it makes sense to spend your time entering for prizes you'll love. By taking the time to enter only the vacation sweepstakes you really want to win, you'll avoid bad experiences.