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Best Sweepstakes to Enter

Geoff Williams

For some people, entering free sweepstakes is a bit of a hobby, and it's easy to see why. After all, if you're entering a giveaway that literally gives you free stuff, and you're not spending money, well, why not?

But before we run through a list of some of the more interesting sweepstakes out there, consider some of these tips:

The bigger prize, the more the odds that you'll pay taxes on it. Just something to remember. If you win a prize over $600, you will have to pay taxes on it.

Read the fine print before you play. You don't, for instance, want to enter every day to win the prize -- and later learn that the first entry was eligible, but the other 400 entries were not.

Enter often. That is, if you get more than one chance to enter a sweepstakes, play often. You'll increase your odds of winning. If you want to win any sweepstakes, well, play a lot of them.

If you see an instant win game, that may be your best bet. That's the opinion of Fred Skoler, a digital games innovator who owns DigiSnax LLC in Barrington, Illinois. He estimates that he has overseen the release of 34,000 sweepstakes in the past eight years.

[See: How to Build an Emergency Fund.]

You might think of the phrase "instant win game" and equate it with lottery tickets, where you might win or lose instantly, but a lot of big brands will do free instant win sweepstakes.

"Sweepstakes come in several varieties, but the best are instant win games," Skoler says. "These games let you know, right away, whether you've won a prize."

He feels that they're also the easiest sweepstakes to win. That said, there are many different kinds of sweepstakes. Some are one-entry sweepstakes (you can only enter once) or daily, weekly or monthly sweepstakes.

There are sweepstakes that you can only enter on social media, through perhaps only Twitter, Facebook, Pinterest or Instagram, or only by sending an email, or something via regular mail. But while there are a lot of different ways you can win a sweepstakes, the one thing in common is that you should look for free sweepstakes from brands you trust.

As you can imagine, especially when it comes from sweepstakes offers coming via email, there are a lot of scammers out there. So if you're looking for sweepstakes to play, you might want to consider these:

-- Expedia CruiseShipCenters -- Win a Dream Vacation 2020 Sweepstakes

-- Cricket Wireless - Win Concert Tickets for a Year Sweepstakes

-- Sandals Resorts - Sandals and Beaches Q1 2020 Sweepstakes

-- Mother Earth News - 50th Anniversary Giveaway

-- HGTV Dream Home 2020 Sweepstakes

-- TruDog Sweepstakes

-- Cheerios Heart Health Promotion with Fitbit Sweepstakes

-- Win a Trip with JAL

-- The Frigo Cheese Heads Chomp vs. Peel Sweepstakes

-- Blue Nile - $10,000 Shopping Spree 2020 Sweepstakes

-- Win Lucky's Gold Sweepstakes

-- 2021 Country Music Cruise Giveaway

Expedia CruiseShipCenters -- Win a Dream Vacation 2020 Sweepstakes

Why you should enter: If you're the type who gets seasick, maybe you shouldn't. But otherwise, this is your chance for you and a special someone or friend to take a Caribbean cruise for two, worth about $5,000.

How often you can enter: One time per person/email. You can enter by clicking on this link, and the official rules are here.

End Date: Feb. 29, 2020

Eligibility: Open to the U.S., Canada and Mexico

Cricket Wireless -- Win Concert Tickets for a Year Sweepstakes

Why you should enter: Do you like concerts? Well, there you go. The title is open to interpretation. Will you get to go to a concert every day for a year? Probably not. Two people will win, and they'll each get a $3,000 gift card to Live Nation, where you could buy a lot of concert tickets, and, yes, stay busy for a year, or if you prefer, stretch it out for longer than a year. But that would be a long title, so they're evidently just going with "win concert tickets for a year."

How often you can enter: Up to five times a day. You can enter by clicking on this link, and the official rules are here.

End Date: May 10, 2020

Eligibility: Anyone in the 50 states and the District of Columbia

[See: How Investing Can Boost Your Emergency Savings.]

Sandals Resorts -- Sandals and Beaches Q1 2020 Sweepstakes

Why you should enter: It's kind of a no-brainer. Four days and three nights at a Sandals or Beaches resort of your choice. These resorts tend to be in some stunningly beautiful countries, like the Bahamas, Saint Lucia, Antigua and Barbados.

How often you can enter: Technically once, although if you get five friends to apply, you could get five more entries. You can enter by clicking on this link, and the official rules can also be found here.

End Date: March 31, 2020

Eligibility: Anyone in the 50 states and the District of Columbia and Canada. Void in Puerto Rico and Quebec.

Mother Earth News -- 50th Anniversary Giveaway

Why you should enter: If your home is important to you, and you feel strongly about the environment, this could be a fun prize package for you. You'll receive things like the Heatmaster SS G200, an outdoor furnace, and an Ambrogio Robot, a robotic mower. The prize value is $24,000.

How often you can enter: One entry per person. You can enter by clicking on this link, and the official rules can be found here.

End Date: Aug. 26, 2020

Eligibility: Eighteen-year-olds and up throughout the 50 United States, excluding the states of New York, Rhode Island, Florida, Alaska, Hawaii and Washington.

HGTV Dream Home 2020 Sweepstakes

Why you should enter: It's a big deal. You win a dream home, $250,000 and an amazing car. The house is on Hilton Head Island, South Carolina. The car is a Honda Passport Elite. It's all valued at $1,787,800.

How often you can enter: Daily. You can enter by clicking on this link, and the official rules can be found here.

End Date: Feb. 19, 2020

Eligibility: Legal residents in the 50 U.S. states and the District of Columbia who are at least 21 years of age or older.

TruDog Sweepstakes

Why you should enter: If you win the grand prize, you'll get a car worth $40,000 and $10,000 in cash. If you are a runner-up (there are two runner-up winners), you'll either get $10,000 or a one-year supply of dog food. And every month that the contest is open, somebody will win $500 or $1,000.

How often you can enter: Daily. You can enter by clicking on this link, and the official rules can also be found here.

End Date: April 30, 2020

Eligibility: Legal residents in the contiguous 48 U.S. states and the District of Columbia who are at least 18 years of age or older.

Cheerios Heart Health Promotion With Fitbit Sweepstakes

Why you should enter: No, you're not winning a new car or a million bucks. The Fitbit you'll win is worth about $100. But there are 9,000 winners, and so maybe your odds of winning aren't too shabby. And if you've been thinking of getting a Fitbit, all the more reason to enter. This is an "instant win" game as well, so you'll know immediately if you've won or lost.

How often you can enter: Up to 10 times during the promotion period. You can enter by clicking on this link, and the official rules are here.

End date: May 1, 2020

Eligibility: Open only to legal residents of the 50 U.S. states and District of Columbia who are 18 years of age or older.

Win a Trip With JAL

Why you should enter: If you love the Olympics and have always wanted to go to Japan, this could be a great deal for you. In a promotion related to the 2020 Olympics, which is being held in Tokyo, Japan Airlines is giving away 50,000 free round-trip tickets to international visitors. Groups of up to four people can win tickets to travel to Japan from July 1 to Sept. 30. The tickets won't be to Tokyo, however, but other cities in Japan. You'll also need to budget for hotels and make sure you have your passport up to date.

How often you can enter: The details haven't been released, but you'll be able to find them once they're up if you click on this link.

End date: Unclear, but the applications will open in late February, and then applications will be on a first-come, first-served basis.

Eligibility: It's open to anyone who doesn't live in Japan. You do have to be a member of the Japan Airlines loyalty program, but if you sign up to become a member, which you can do here, before the contest opens in late February, that problem is solved.

[See: 9 Secrets to Save Money on a Shoestring Budget.]

The Frigo Cheese Heads Chomp vs. Peel Sweepstakes

Why you should enter: We realize that this sweepstakes contest is a little -- ahem -- cheesy, but wouldn't it be fun to tell your friends that you won a year's supply of string cheese? Forty grand prize winners will win free cheese for a year (well, 24 coupons). The retail value of the prize is $144.

How often you can enter: Once a day. You can enter by clicking on this link, and the official rules can be found here.

End date: March 31, 2020

Eligibility: Eighteen-year-olds and up in the 50 states and the District of Columbia.

Blue Nile -- $10,000 Shopping Spree 2020 Sweepstakes

Why you should enter: Do you like shopping? Do you like jewelry? Then you may consider this sweepstakes a gem. The winner gets a Blue Nile shopping spree worth $10,000. BlueNile.com is an online jewelry store that has been around since 1999, and so, yes, you'll be getting a $10,000 gift card.

Entry Frequency: One time per person/email, or two if you make a purchase and do a product review. You can enter by clicking on this link, and the official rules are here.

End Date: March 3, 2020

Eligibility: Legal residents who are 18 and older in the 50 U.S. states, Canada (except Quebec) and the United Kingdom.

Win Lucky's Gold Sweepstakes

Why you should enter: This is an "instant win" game, so you'll know promptly if you won or lost. There's also a lot of prizes being given out -- over 10,500. Alas, this is not actual gold you'll be winning but an offering from the cereal Lucky Charms. Still, you will surely feel lucky if you win a prize, which are mostly $50 Visa gift cards.

Entry Frequency: You can play up to 15 times. You can enter by clicking on this link, and the official rules are here.

End Date: May 31, 2020

Eligibility: Legal residents who are 18 years old and older and who live in the 50 U.S. states, the District of Columbia, the U.S. Virgin Islands or Puerto Rico.

2021 Country Music Cruise Giveaway

Why you should enter: If you love country music, you should enter. If you're somebody who hates country music, this is not for you. This is a week-long cruise for two people on board the 2021 Country Music Cruise. Numerous country groups and stars will be performing, including Lee Greenwood and The Oak Ridge Boys, and the cruise leaves from Fort Lauderdale, Florida, and goes to the Bahamas, Key West, Florida, and Cozumel, Mexico.

Entry Frequency: Once a day, per person. You can enter by clicking on this link, and the official rules are here.

End Date: Dec. 4, 2020

Eligibility: Open to residents of the United States (void in Alaska, Hawaii, Rhode Island and U.S. territories).



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