Holiday Competitions 2019 – Updated Weekly!

Looking to travel more without spending more? I am a big advocate for entering holiday competitions to try to win a holiday. 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 travel competitions 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, UK holiday 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.

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.

Holiday competitions 2019:

The newest travel competitions will be at the top of the page and will be updated with new holiday competitions every other day, so be sure to bookmark this page and keep checking back. 

Please note, due to my location, most competitions will be for UK applicants, however, check the competition terms and conditions to be sure.

May the odds be ever in your favour!

Win a 5-star break to Edinburgh

The winner and a guest will stay for three nights, B&B, at The Dunstane Houses, Edinburgh’s newest five-star hotel, which was one of The Sunday Times Scottish hotels of the year in 2018. One dinner for two (excluding drinks) is included in the prize. Competition closes on August 20th 2019.

Win an 8 night stay in South Africa

The winner will win a holiday for 2 in South Africa including one way transfer for 2 people from Port Elizabeth Airport to Garden Court Kings Beach, 2 nights for 2 people sharing in a standard double room on bed & breakfast basis at Garden Court Kings Beach, 4 Day / 3 night Garden Route Uncovered guided tour with Springbok Atlas for 2 people sharing, 3 nights for 2 people sharing a standard double room on a bed & breakfast basis at Southern Sun, The Cullinan, a lunch or dinner cruise for 2 people on The Alba Floating Restaurant, one way transfer for 2 people from The Cullinan hotel to Cape Town International Airport. Please note flights are excluded from this prize. Competition closes on September 30th 2019.

Win a trip to Venice

Win a trip to Italy by simply guessing the number of water bottles which will be refilled by the Excels water stations in 2019. The prize includes return flights to Venice for two people and £1,000 for accommodation and spending money. Competition closes January 5th 2020.

Win a Family Holiday worth £1000

From holidays, getaways and everything in between, Joules clothing want to see just what ‘summer of fun’ means to you and your family. To enter you need to upload a photo-based around the theme ‘summer of fun’ – be creative and make your photo stand out! The chosen winner will win a £1000 voucher as well as a £500 Joules Clothing voucher. Competition closes on August 31st 2019.

Win a dog-friendly break 

Here’s your chance to win a dog-friendly break for two people at Mosborough Hall Hotel in Sheffield, on the edge of the Peak District National Park.

The prize includes:

  • A one night, dog-friendly stay for two people (with your pet!)
  • Delicious breakfast the following morning
  • An evening meal with your dog in the cosy bar area

Competition closes on August 19th 2019

Win a trip to New York

Answer the question in the Event with Legend contest and you can win a trip for two including two nights hotel accommodation, flights and a three-course meal at Carragher’s Pub & Restaurant.  Competition closes August 31st 2019.

Win a luxury safari to Kenya

Mahlatini is delighted to offer you the chance to win an unforgettable 7 nights trip for two to one of Africa’s most iconic and spectacular safari destinations.

This amazing prize includes:

  • Return International flights to the value of £500 per person
  • Two nights at Saruni Samburu, on an all-inclusive basis
  • Two nights at Saruni Rhino, on an all-inclusive basis
  • Three nights at Saruni Mara, on an all-inclusive basis
  • Full game drive-packages in shared 4×4 vehicles with guides
  • Rhino Tracking Experience (1 per day)
  • Light aircraft flights and transfers
  • Conservation fees
  • Additional extras include massage treatments, guided bush walks, sundowner and picnic excursions

Competition closes on September 30th 2019.

Win return flights to Japan for two

British Airways celebrates its centenary this year, that’s an impressive 100 years of connecting Britain to the rest of the world and the rest of the world to us. To celebrate this anniversary, Bright Sun would like to give you the opportunity to win a pair of return flights in World Traveller economy class to Osaka, a newly launched British Airways route. Competition closes on August 23rd 2019.

Win a trip to Matera, Italy

Win a 4-day trip to the historic town of Matera in Southern Italy. The prize, sponsored by Italian furniture makers Nicoletti Home, includes return flights and transfers to Matera, a city tour and three nights in Matera’s luxury 5-star Aquatio cave hotel and spa. Competition closes on September 9th 2019.

Win an Amazing Seven Night Trip to Canada

Enter for your chance to win a 7 night holiday to Canada! The prize includes:

·         Roundtrip flights to Toronto, Canada from either London Gatwick, Manchester or Glasgow

·         7 days Intermediate motorhome hire with Canadream

·         1 night hotel accommodation in Toronto for the night before the motorhome trip commences

Competition closes September 30th 2019.

Win in a luxury four-night spa holiday in Portugal 

For this competition prize, one lucky winner and a friend will win an incredible four-night stay at Cegonha. As well as full-board accommodation, the pair will get a wellness evaluation, nutrition and wellbeing consultation, reiki, cranial-sacral therapy, energetic healing therapy, reflexology, body scrub, relaxing massage, flotation session and an anti-ageing facial.
Competition closes on September 1st 2019.


Comping tip: Comping, if done right, can be a really lucrative as well as fun hobby. While a big part of it is done to luck, you can also increase your chances of winning big if you know what to do.

If you are planning on making comping a hobby then I recommend investing in the Super Lucky Secrets book by Di Coke (currently available in paperback and E-book). Di has bagged over £300,000 of prizes by entering prize promotions – and now you can read a hundred of her tried and tested tips on being a successful winner.

Win the ultimate Texas getaway to Dallas and Fort Worth 

Visit Dallas and Visit Fort Worth have teamed up to give two lucky people the chance to experience the Texan lifestyle and to indulge in some of the best arts, culture, BBQ and more in Texas. Competition closes September 30th 2019.

Win a two-night getaway in Venice for two

Flying in from London, you’ll rest for two nights in a central, 4-star hotel. From here, you’ll be perfectly positioned to discover Venice’s marble palaces, historic squares and towering Basilica, before floating along in a gondola on Venice’s most famous of glistening waterways, the Grand Canal. Competition closes on October 31st 2019.

Travel 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.

Win An Amazing Seven-Night Trip to Canada

Enter for your chance to win a 7 night holiday to Canada.
The prize includes:
· Roundtrip flights to Toronto, Canada from either London Gatwick, Manchester or Glasgow
· 7 days Intermediate motorhome hire with Canadream
· 1 night hotel accommodation in Toronto for the night before the motorhome trip commences

Competition closes on September 30th 2019.

Holiday competition tip:  For email entries, draft and save a template email with your name, email, address and telephone number, so you can fire it off quickly. Remember to leave a space for the answer.

Win a trip to Machu Picchu

Cafe Direct is going one lucky person and a friend the chance to fly to Peru to hike Machu Picchu as well as explore the Sacred Valley. Competition closes October 31st 2019.

Win a 10 night trip of a lifetime to Japan 

Win a 10 night trip to Tokyo by waxing your nose! Yep you heard me correctly, Kenashii would like you to film yourself waxing your nose then upload it to social media for everyone to see – only the bravest will win the trip of a lifetime to Japan. Competition closes 31st December 2019.

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Remember to check back weekly for new travel competitions! If you do win a holiday which you have found through a travel competition on this page then I would love to know. Please be sure to send me a tweet at @yokomeshiuk so I can find out all about your win and next adventure.

Travel competitions I have won:

Return flights for two to Iceland with Wow Air – won via a tweet saying where I would like to go.

An all-inclusive city break to Barcelona with spending money – Creative competition with a photo.

An eco-friendly travel accessories gift bag worth over £50 – Guessing a destination on Instagram.

Tickets to a beer festival in Germany plus exclusive camping – Answering a question via Instagram.