5 Holiday Travel Contests to Enter, Plus Enter Day 6 of the 12 Days of Giveaways

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Holiday contests offer some of the best giveaways of the year. Prizes range from small trinkets or discounts to phenomenal tropical all-expenses-paid family vacations.

After shopping for everyone on your list, could you use a little holiday magic of your own this year? Below are some of the coolest holiday travel contests to enter in 2017.

5. Hallmark’s Countdown to Christmas Sweepstakes where 4 lucky grand prize winners will each receive Delta Vacations round trip air travel to enjoy a three day whirlwind trip for four people at one of the Gaylord Hotel resorts.

You can enter daily through Monday, December 25, 2017 at 8:59 PM PST.

4. SassyMamaHK has a contest where you can win a staycation at the Mandarin Oriental Hong Kong, worth $12,500. The prize comes complete with Harbor View room, breakfast for two, couples massage, champagne, and VIP status at the hotel.

Harbor view room, Mandarin Oriental Hong Kong (photo credit: Mandarin Oriental)

You must be a resident of Hong Kong to enter, and all entries must be received by December 31, 2017.

3. Le Club Accorhotels is running 31 days of giveaways including daily bonus Rewards points, free stays, partner gifts, and Elite experiences.

You can enter daily through December 31, 2017.

2. Norwegian Reward, the loyalty program of Norwegian Airlines, has a Christmas countdown where you can search for Travelling Santa and win daily CashPoints. The grand prize winner will receive 10,000 CashPoints on Christmas Day.

You can enter daily through December 25, 2017.

1. JetSetFam is running an outstanding giveaway with over 43 prizes worth $20,000. Highlights include luxury hotel stays (think Loews Hotel 1000 in Seattle, Omni La Costa Resort, Hotel Del Coronado, etc.) and travel experiences.

You can enter in several ways through December 24, 2017.

Of course, the cool contests to enter include the Magic of Miles 12 Days of Giveaways.

Today is Day 6, and to win today’s holiday goodie bag, let me know in the comments below what your coolest contest win has been. If you are one of those people that doesn’t usually win contests you can say that too.

Today’s Magic of Miles contest ends at 9pm PST tonight. Click here to read full contest details.

Good luck to all!

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  1. Carly Bogen

    I never win anything! This would be a great start 🙂

  2. paul v

    I pretty much got a rock (I think I won an electric train as a kid, and a map as an adult).

  3. Robin W.

    I won a week-long trip to Niagara Falls with Motel 6 a few years ago.

  4. Robin W.

    I, also, won a box of science fiction books that arrive, by surprise, at my house. I was really excited about that as they were all by one of my favorite authors. I had entered the contest and then forgot all about it.

  5. Robin W.

    I LOVE contests and the possibility of winning.

  6. cnmaz

    I think my most exciting win has been concert tickets over the radio.

  7. cnmaz

    I did have a fun win when I received a first class British Airways amenity kit.

  8. cnmaz

    I would really like to win one of your giveaways this year. Thank you for posting information on some of these other contests.

  9. Dan

    I won a Hawaiian Tropic trip to Honolulu with airfare for 2, lodging at the Turtle Bay Resort, all meals at the resort, entrance to Miss Hawaiian Tropic events, and I think some cash to cover any taxes.

  10. Dan

    Another one was a Lufthansa First Class Duck

  11. Dan

    A third was airfare for 2, 3 nights at the Las Vegas Wynn, and $1,500 to spend at the hotel (I used to enter a lot of contests).

  12. Jeff M.

    Winning the 25 GOGO passes was a great win recently.

  13. Jim F.

    My coolest contest win — hands down — was a radio contest in 1981 in which I won a brand new Chevrolet Monte Carlo!

  14. Steve

    The Accor contest is great, I get 100 points almost every day!

  15. Jeff M.

    Winning a trip to Myrtle Beach.

  16. Jeff M.

    I haven’t won it yet, but winning a trip to the moon. My wife keeps saying she’s going to send me there. 🙂

  17. Sidney cook

    I once won a Royal Caribbean cruise from a Coca Cola sweepstakes

  18. Sidney cook

    Not winning much but then I don’t enter many contests

  19. Sidney cook

    Would love the Gogo passes

  20. Paul

    I won a prize box from you

  21. phil gold

    won a nice set of headphones a few years back. Thanks

  22. Giant Sis

    I got our Jeep paid off when we owed almost $25,000 on it! My husband was SO thrilled!

  23. Giant Sis

    I’ll go check out the contests you listed and maybe have a win from them!

  24. Giant Sis

    Thanks for sprinkling so much joy with your daily giveaways!

  25. mike murphy

    won a $500 prize from Rubios for filling out their online survey

  26. S. Bradford

    I have won some fabulous things in my life. I consider myself lucky in general (not just winning contests) but maybe it has more to do with my general optimism that makes me see things through an “I am lucky” lens. One great prize I won was a trip to be a “Hydration Specialist” to Tiger Woods on the 9th hole of some golf thing. It was supposed to be his first appearance back after a long injury. A week before the trip, scandal broke and he had the troubles in his home life and couldn’t make it. We still enjoyed our paid vacation to watch a bunch of golf in Southern California. The week long trip for four included airfare, resort hotel, endless days of Golf watching with VIP passes and entertainment (food and drinks) access, car rental, Nike swag bags, some cash, and probably some other stuff. None of us are particular golf fans but it was worth it for the experience. Something I would not have done had I not won it. I did have to pay taxes on the value of the trip, but it was still worth it.

  27. S. Bradford

    Another great thing that I won was a huge prize assortment from Gogo many years ago when they hosted a 12 days of giving Holiday Season giveaway. I won the final and biggest prize. I was a supporter before that, but really a fan of Gogo afterward. The package didn’t come with any Gogo passes. However, whenever I have flown since I have never minded paying for Gogo when I need to use the internet in flight.

  28. Chris

    I think I’m due for a win this year.

  29. Chris

    But I did win a contest that Wandering Armenian was running a few years ago.

  30. Chris

    It was fun opening a grab bag of travel swag.


    I won third prize, a skateboard, in a bike shop raffle in Peru Indiana in 1979. Much to the chagrin of my brothers. Still can’t skate..

  32. Joe-SC1

    I think my coolest win was an iPad Mini 2 a few years back. Thanks.

  33. S. Bradford

    When I worked for a sportswear company I won an in-house contest and was able to select a great winter jacket for my husband. Every winter we are thankful to have it. Not that we couldn’t acquire another winter jacket, but this one has a particularly nice cut and is super warm and waterproof. He looks great in it.

  34. Joe-SC1

    I also won a Kindle Fire 2nd Generation more than a few years back that was also very cool. Thanks.

  35. Joe-SC1

    Then again, fitting in with the travel theme, I did win a year of ExpertFlyer Pro in 2015 that was cool when I flew a bit more than I do now.

  36. Teddy

    Most of my winnings are hotel stays

  37. Teddy

    Tho, early in my contest hunting days, I used to win smaller trinkets (think tumbler, egg poacher, stuff like that)

  38. Teddy

    Lately it’s been a dry spell though. C’mon, Christmas is supposed to be a time of sharing, yes?

  39. JRG

    I won a $900 coffee table once; not my style so I sold it for $250.

  40. Dwi S

    Coolest contest win? Gosh, it’s rather hard to say. When I first started, I suppose it was a Bose QuietComfort headphones. A bit too big for my head though.

  41. Dwi S

    Then I moved up to hotel stays. A night here, two nights there. That was when I first started to travel a lot. Fun times!

  42. Dwi S

    Lately I haven’t won anything “cool” though. Is it because my standard has increased, or is it just getting harder to win anything?

  43. Kiki

    Once I heard the end of a contest-be the 10th caller, but I didn’t hear for what prize. I called and won. The female disk jockey said she was exited a woman had won. Then I found out the prize was two tickets to a monster truck pull. (Not my thing-but magicofmiles goodie bags are!)

  44. J.


  45. J.

    Accor points, too.

  46. Gino

    I’ve won an assortment of random small things over the years from contests and radio giveaways, but nothing big like a car or trip. Just a basket of scratch-offs and some HOOU coupons. I did win on the scratch-offs ($10) and a drink is always a welcome treat when flying DL!

  47. Ricky

    I won a brand new drone last holiday season, definitely the coolest gadget I own!

  48. Jonathan

    I won 250 dollars in my Chase account last year. So random, but all of a sudden I had 250 more than the day before. The strange thing was, there was no notification about winning.

  49. Ed

    I was blessed to win 2 Alaska Airlines tickets with the Alaska virgin merger.

  50. Abhishek D

    A trip to Spain

  51. Dotti cahill

    Nothing exciting but 2 drink coupons

  52. Rich

    A $50 Amex gift card

  53. Chris

    Only thing I’ve won in United drink tickets

  54. rmh

    i only won publishers clearing house once. and it was only 25 million…

  55. rmh

    thanks for all the contest information

  56. r m h

    thanks for your site

  57. Phxbne

    My coolest was a $200 gift card

  58. James Turner

    I was fortunate enough to win a Garmin Fenix 3 smart watch, Sony Action Cam, & a portable battery pack from MasterCard & IHG 2 years ago!

  59. Jean

    I don’t usually win, but I keep trying

  60. Vet&Banker

    Just won a Caribbean cruise, which was fantastic.

  61. Vet&Banker

    Also, my family won an A&P Disney trip when I was small. So many ride tickets that we gave them away to strangers.

  62. Vet&Banker

    Winning this would be a nice way to end the holidays.

  63. Bob

    I won one of the smaller prizes for 10,000 AAdvantage miles several years back.

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