Holiday Competitions

Looking to travel more without spending more? I am a big advocate for entering holiday competitions. Over the past 18 months, I have won a trip to Barcelona, flights to Iceland and various other day trips. Winning holiday competitions are a great way to travel more without spending any money, and while you may not win them all (or any to start with!), it goes without saying, the more you enter, the more chance you have.

On this page, I will round-up all the best holiday competitions I find on the internet, from city break competitions, to once in a lifetime holidays. They will all be opportunities to win a holiday, all you need to do is follow the instructions to enter and think positive thoughts.

lady sitting on cliff edge in jersey

Win a holiday competition tip: I find I have better chances with ‘effort competitions’ or ‘creative competitions’, this means competitions where you have to do more than just sign up for something for entry. The reason behind this is because fewer people enter as a lot of people cannot be bothered. The more effort you put in, the better your chance of winning.

The newest competitions will be at the top of the page and will be updated with new holiday competitions weekly.

May the odds be ever in your favour!

Win a holiday to New York 

How about winning a four-night luxury city break to New York for two? All you need to do is enter the very simple multiple choice question and fill in your details. Competition closes September 9th 2018.

Win a return flight to Japan 

Fancy visiting Tokyo or Osaka? How about spending a few weeks travelling around Japan? Win a return flight to Japan with Japan Airlines for one. All you need to do is sign up for a newsletter. Competition ends on August 14th 2018.

Win a holiday to South Africa 

Win a trip of a lifetime to one my favourite countries – South Africa! This includes a 14-day itinerary along the Garden Route includes a safari at the Addo Elephant National Park and Wine tasting in Cape Town. Competition ends November 23rd 2018.

Win a trip for two to Argentina

This incredible prize also includes a Trivento Winery tour across sunny Mendoza, a real Gaucho trip, a bike ride through the wine country and tango lessons for two, plus £500 spending money. To enter you must complete the multiple choice question. Competition ends August 13th 2018.

Win a city break to Paris, France

Win a romantic city break for two to Paris, including Eurostar Tickets with Super Break. Answer a simple question to be in with a chance of winning. Competition ends August 31st 2018.

Holiday competition tip: A lot of competitions will ask you to sign up for their newsletter in order to be in with a chance of winning. To combat your inbox being filled with emails, create a new email just for comping, this way all emails will be in there and not your main email.

Use your photography skills to win a luxury journey through Egypt

One lucky person(and a plus one) will win the chance to spend five nights aboard the beautiful Steam Ship Sudan while exploring the wonders of Egypt’s River Nile, with all offshore activities, meals and flight voucher included. Upload your best travel shot to Instagram using the #originaltravel, tag and follow @originaltravel. Competition ends August 31st 2018.

Win a weekend in Barcelona plus a £200 Bon Marche voucher 

Win a weekend for two in Barcelona, Spain as well as  £200 Bon Marche clothing voucher to ensure you have the perfect outfits for your trip. Simply fill out your details to be in with a chance of winning. Competition ends August 31st 2018.

Kid’s Competition to win flights for the whole family with Easyjet

Children can get involved in comping as well. Let your kid’s imagination run wild and it could win you Easyjet flights for the whole family. Simply get your child to finish this sentence: “I looked out of the plane window and saw…”. Competition closes on August 31st 2018.

Win a holiday for two to the Florida Keys and Miami 

Win a 7 night holiday to the beautiful Florida Keys, including hotels, flights with Virgin Atlantic and rental car. Enter the multiple choice question to be in with a chance of winning. Competition ends September 6th 2018.

Use your creative to win a walking holiday in Germany

What is your interpretation of a slow moment? Take a photo, put pen to paper, or record a short video and share it to be in with a chance of winning an InnTravel trip. Be as imaginative as possible to stand out. The competition runs monthly with the overall winner being selected in January 2019.

Win two Eurostar tickets to Amsterdam

Win travel tickets to Amsterdam courtesy of King’s Cross, all you need to do is fill out your details. Competition ends September 29th 2018.

Sleeping under the stars in Reykjavik

Spend the night in a futuristic and fully transparent bubble in the middle of the tranquil Icelandic landscape  – perfect for gazing up at the moon and stars. Team this with a visit to the Thingvellir National Park, Geysir hot springs and the Gullfoss waterfall. All you need to do is answer a multiple choice question on the new Penguin book Artemis. Competition closes on September 3rd 2018.

Win a £2500 holiday voucher

Book the holiday of your dreams by winning a £2500 Virgin Holiday voucher to spend however you please thanks for Cravendale. All you need to do is enter your details on the form. Competition ends August 13th 2018.

Win a city break to Hamburg, Germany 

Hamburg has become a really popular city break destination over the past year, so why not try to win a trip to discover it yourself? All you need to do is follow @hamburgontour and @theartshelf on Twitter and follow the instructions on the website to inform them. Competition ends August 18th 2018.

Win an all-inclusive adventure holiday to Whistler, Canada. 

This prize looks incredible, and I urge everyone to enter this one. As well as flights and accommodation, Whistler tourism is also including so many different incredible activities during your time there. All you need to do is fill out your details. Competition ends September 27th 2018.

Win a city break to Tallinn, Estonia 

Win a 4 night holiday to Tallinn, including return flights, accommodation and an excursion trip for your chance to see wild bears. All you need to know is how many years of independence Estonia is celebrating in 2018. Competition ends on September 30th 2018.


Remember to check back weekly for new competitions and if you win anything, please do let me know!