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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

Holiday competitions 2020:

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 £2000 trip with Holiday Pirates 

HolidayPirates is giving away a trip worth £2,000! Dreaming of holidays far away? Enter the contest for a chance to win a luxurious vacation that’s valid until 2021!

Competition closes September 27th 2020

Win a wellness weekend in Croatia 

Vote in the Soul Awards and win! Simply vote for your favourite spiritual people and experts that you feel are deserving of an accolade, and you’ll be automatically entered into a prize draw to win a luxury stay in Croatia, worth £1,100!

Competition closes October 15th 2020

Win a trip for 2 to Thailand 

Open to travellers between 18 – 40 years old. An unforgettable trip for two in Thailand with TruTravels and TourRadar could be yours. The winner can choose from 3 trips ranging from 7 to 14 days.

Note: Flights not included.

You can also increase your chance of winning by 10 by completing a quick treasure hunt near the end of the entry

Competition closes on 28th September 2020

Win a honeymoon in The Maldives!

Kuoni is offering one lucky winner the chance to win a honeymoon on one of their exclusive islands: the luxurious and newly-styled Maafushivaru, which has just undergone a complete refresh.  You can enter now and travel later, with the peace of mind that you will be fully looked after.

Competition closes November 5th 2020

Win a Classic Lodges Hotel Break

The sender of the winning photograph will enjoy a three-course dinner for two before settling down for a good night’s sleep in a double or twin bedroom. The next morning, indulge in a full English or continental breakfast, before enjoying a stroll around the historical towns or beautiful countryside near to all 14 Classic Lodges hotels’.

Competition ends October 8th 2020

Win a 7 Night Skiing Holiday in the French Alps

Here is your chance to win a seven-night holiday for up to five people in the stunning Isère resort of Alpe d’Huez, boasting 250km of slopes and magnificent views of the Alps, including Mont Blanc. The prize includes apartment accommodation, fully inclusive ski passes and a Eurotunnel Long Stay Flexiplus travel ticket for your vehicle and all passengers.

The prize partner is Isere Tourism who is offering a 7-night stay for 5 people in a minimum 3 Star apartment with 2 bedrooms or 1 bedroom + cabin, in the resort of Alpe d’Huez. The prize includes 5 x 6-day Grand Domaine Ski passes (excluding insurance) in Alpe d’Huez.

Competition ends November 25th 2020 

Win a Four-Night Stay at One of Turkeys Most Beautiful Hotels

Condé Nast Traveller is giving away a four-night stay at one of Turkey’s loveliest hotels, plus dinner at its hillside Anatolian restaurant and a complimentary wine tasting.

The winner and their guest will stay at Argos in Cappadocia, which is located in the eponymous semi-arid region of Cappadocia in central Turkey known for its distinctive tall cone-shaped rock formations. The hotel sits on the slopes of the area’s highest peak, Mount Erciyes, and staying in one of the smart deluxe rooms you’ll wake up to views across the town of Uchisar, Pigeon Valley and the distant hills beyond. Spend the day lounging by the pool, treat yourself to a relaxing massage in the Turkish baths and spa, or head out to explore the volcanic landscapes and the gorge at Ihlara.

One dinner for two at the hotel’s Seki restaurant is included. Set inside one of the oldest and largest monasteries in the world, Seki serves classic Anatolian food using local ingredients, with dishes such as traditional kebabs and hand-rolled pasta. A wine-tasting experience for two is also part of the prize, so you can spend an evening sampling the restaurant’s own mountainside vineyard wines as well as some of the best bottles from around the world.

Competition ends October 8th 2020

Win a Two Night Glamping Holiday in Yorkshire

Wigwam® Holidays Forcett Grange is located near Richmond, North Yorkshire. Their stunning site includes spacious, fully en-suite cabins and private hot tubs in breathtaking surroundings. The site is completely step-free, meaning easy access for everyone. One lucky winner will win a two-night break for up to two adults and two children, subject to availability.

Competition closes September 17th 2020

Win a Private Photography Workshop for You and One Other Person & 2 Night Stay in North Yorkshire

The winner will be staying for two nights on a bed and breakfast basis in either a twin or double room at  Carlton Lodge in the beautiful market town Helmsley on the edge of the North York Moors National Park.

Your workshop will start at 6 pm on Friday evening and will run until 5 pm on Sunday. It is exclusively for you and one other person. During the workshop, you will visit and photograph some of the most iconic locations on the North York Moors and Yorkshire Coast.

Competition closes September 30th 2020.


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.


Win a family holiday to New Zealand worth £13,700

Family Traveller has teamed up with VIVID Travel to offer one lucky family the chance to win an incredible 17-day adventure around New Zealand worth £13,700.

Prize includes:

  • Return economy international flights from London Heathrow with Singapore Airways
  • Economy domestic flights
  • All accommodation throughout (mix of room-only and breakfast-included)
  • Transfers from Auckland airport on arrival
  • Car hire
  • All tours and admissions stated including Sky Tower admission, day tour of Coromandel Peninsula, Hobbiton Movie Set Tour, Rotorua Sights and Skyline Gondola Tour, Waitomo Caves tour, Shotover Jetboat Ride, scenic flight to and from Milford Sound, Milford Sound Nature Cruise, and Safari of the Scenes tour

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 8 day South Africa trip including safari

This magnificent trip to South Africa is a once-in-a-lifetime experience. From a private safari tour at Kruger National Park, one of Africa’s largest game reserves and home to the “Big Five”, to South African wine tastings at the beautiful vineyard towns of Franschhoek and Stellenbosch, this is no ordinary holiday. You can win this luxurious eight-night trip to South Africa for yourself and a guest.

Competition ends September 15th 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 luxury spa break in Bath Spa

The Gainsborough is delighted to offer one lucky reader the chance to win a two-night midweek stay for two at the iconic hotel. The winner will also receive complimentary valet parking, daily breakfast and one dinner in the hotel’s restaurant- Dan Moon at The Gainsborough. Staying in one of the hotel’s spacious suites, the winner can look forward to picturesque city views from the comfort of a contemporary two-poster bed or the suite’s generous sofa.

Competition ends October 5th 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.


Subscribe to my mailing list to receive a round-up of the best competitions to your inbox each month!

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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.