Travel & Holiday Competitions 2020 – Updated Weekly!

sunset view from plane, flying with cbd oil

Do you want to win your next holiday? Here is my weekly round-up of the best 2020 travel competitions.

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.

family standing at the beach on holiday won on a travel competition

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 trip for 2 to Las Vegas 

Dr Ed is giving away the ultimate trip to Las Vegas. This prize includes:

  • Return flights for two people from the UK to Las Vegas
  • A 5 night stay in a Las Vegas Strip Hotel
  • $500 spending money

Competition closes on February 7th 2020.

Win a family holiday to Corfu

There are two prizes. Each prize is a seven-night holiday for two adults (18+) and two children aged 11 or under on return date of travel, sharing a family room at the four-star Labranda Sandy Beach Resort, Corfu on an all-inclusive basis.
The prize includes economy return flights from each winner’s choice of London, Birmingham or Manchester airports to Corfu.

Closing date 4th February 2020.

Win a spa break for two 

Co-op is offering one lucky reader the chance to win a classic spa break for two gift voucher, courtesy of

Valid at more than 300 stunning destinations in the UK and Ireland, it includes one night’s B&B, full use of the spa facilities and a 25-minute treatment per person.

The closing date is 28 January 2020.

Win a Week-Long Retreat At Soul & Surf In Sri Lanka

The seven-night stay includes breakfast, lunch and two-course dinner every day, five two-hour surfing lessons plus an extra five at sunset, five yoga classes and additional meditation sessions and Yoga.
Located on the southern coast, the winner and their guest will be invited to join yoga classes and surfing lessons throughout the week.

Competition closes on January 23rd 2020.

Win a holiday to the Maldives for two 

Thanks for Monster Energy Drink you could win a 4-night luxury trip to the Maldives for 2 people (incl flights) with surf lessons and yoga activities during Maud Le Car. Two trips up for grabs!

Competition closes on April 30th 2020.

Win an Overnight Spa Break

– An overnight stay for two at a spa venue of your choice

– One night’s dinner, bed and breakfast

– One blissful 60-minute treatment per person

– Full use of the spa facilities

– Use of robe, towel and slippers

– A £250 Evans gift card

Competition closes on 18th January 2020.

Win a Vegan Cookery Retreat In Portugal

Enter your details in this free draw with Psychologies and you can win a week-long retreat in Portugal, worth £2,499. Please note flights are not included. Competition closes on January 12th 2020.

Win a holiday in France

Enter your details in this free draw with French Entree and you can win a weeks stay for up to eight people at the Nicotiana holiday home. Competition closes January 31st 2020.

Win a Resilience and Flow retreat in Morocco worth £1,950

Enter your details in this free draw with Psychologies and you can win a place on the Resilience and Flow week-long retreat at Resurface Surf-Therapy Retreats. Please note flights are not included. Competition closes on February 17th 2020.

Win a luxury Caribbean Holiday for two worth £5000 

To celebrate the new year, Wallis has partnered with Sandals Resorts to give one lucky winner the chance to WIN their dream holiday to the Caribbean, including a luxury seven-night all-inclusive stay for two at Sandals Halcyon Beach Resort, St Lucia, plus return economy flights. Competition closes on January 18th 2020.

Win a Seven-Night Stay for Two on Grand Cayman

Food and Travel Magazine have teamed up with the Cayman Islands Department of Tourism to offer one lucky reader a luxurious seven-night break for two on the paradise island of Grand Cayman at Westin Grand Cayman Seven Mile Beach Resort & Spa. Competition closes on February 14th 2020.

Win flights to New York City 

Win 2 flights to New York City with Virgin Atlantic by playing the addictive game Suitcase Stack. Competition closes on January 31st 2020.

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 six-night holiday in the Maasai Mara

Courtesy of National Geographic and Asilia Africa the winner and a guest will travel to the Maasai Mara for a six-day, five-night walking safari. Covering between 10-12 miles per day, you will stay in a mix of fly camps and permanent camps, with all the logistics and transfers taken care of. The prize includes return flights from London to Nairobi. Competition closes Friday 31 January 2020.

Win a luxury mountain trip to Austria

The prize consists of two return economy flights from London to Salzburg (either from Stanstead with Ryanair or from Gatwick with British Airways), four nights at the Grossarler Hof Hotel in Grossarl, twin or double Tower Room on a half-board basis, two days bicycle hire and Grossarl Summer Card (alternatively two days ski hire available and ski lift pass for winter departures), two spa treatments in the Erlenreich Relax & Spa and private return airport transfers. Competition closes on 9th February 2020.

Maximise your chances of winning holiday competitions by reading 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 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.

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 a trip to Porto, Portugal

The first prizes is a trip to the vibrant city of Porto for two people including flights, hotel accommodation, dinner and an exclusive port tasting at the award-winning Cockburn’s Lodge. For the second prize, there are 24 bottles of Cockburn’s Quinta dos Canais Vintage Port up for grabs, and for the third, there are 5,000 bars of 35g Green & Black’s Organic Chocolate to be won. Competition closes January 12th 2020.

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.


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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.