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 VIP trip to the Legoland Windsor Resort AND £1000

Here is your chance to win an amazing family trip to the LEGOLAND® Windsor Resort, plus £1000 to give away to one lucky winner! All you need to do in answer a simple question. 

Competition ends July 12th 2020

Win two places on the southern route of the Lanka Challenge

Your chance to win two places on the southern route of the Lanka Challenge (Sept 2021, Sri Lanka) for you and a friend, including tuk-tuk hire and stays in high quality, locally-owned hotels and campsites.

Competition closes on 12th August 2020.

Win 7 Nights on the Beautiful Caribbean Island of Nevis

Get the Chance to Experience the Unspoilt, Relaxed, and Easy-Going Island of Nevis, with Wide Open Spaces and a Rich Cultural Heritage.
This Fabulous Prize comprises Two Amazing 4 StarResorts located on Nevis Island. Four Nights at Montpelier Plantation and Beach, a boutique hideaway offering Relais & Chateaux hospitality where you can let the rest of the world slip away. Three Nights at Nisbet Plantation Beach Club, the Caribbean’s only historic Plantation Hotel located directly on a beach. Secluded, peaceful and tranquil, it is the quintessential island hideaway.

Competition closes August 3rd 2020

Win a luxury family stay at the iconic Lion Lodge at Port Lympne Hotel & Reserve in Kent

Port Lympne Reserve is giving one night stay for a family of four (2 x adults and 2 x children) at our Lion Lodge for one lucky winner.

Set within our 600 acres of parkland, the lodge boasts large windows with reinforced glass overlooking the lion enclosure. The luxurious interior boasts a king-sized bed in the master bedroom, a mezzanine floor featuring two single beds and an indulgent bathroom complete with a walk-in Monsoon shower and Bamford toiletries.

But that’s not all, the prize also includes a AAA Safari! This VIP behind the scenes experience gives you the chance to have an up-close and personal visit to one of Africa’s big five – the black rhino – as part of a Land Rover safari through over 100 acres of Kentish Savannah where animals such as giraffe, zebra, wildebeest, ostrich and many more animals roam free. 

Competition closes July 31st 2020

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

Win a UK weekend break with Forest Holidays

Forest Holidays are offering one lucky winner and up to 3 guests a fabulous 3-night weekend break in a cabin set in enchanting woodland. 

Accommodation will be in a fully equipped two-bedroom cabin on a self-catering basis, sleeping up to four people. Each cabin comes with soaring windows with dramatic forest views and your own private hot tub from which to stargaze late into the night.

Choose from one of 10 stunning locations exclusively, subject to availability. 

Competition closes August 2nd 2020.

Win a 12-night cruise of the British Isles

One lucky person will win a 12 night British Isles cruise for them and up to three close friends or family thanks to Princess Cruises.

This relaxing trip aboard Crown Princess departs Southampton and sails clockwise around the British Isles, stopping at Guernsey, Cork, Dublin, Belfast, Glasgow (Greenock), Invergordon and Edinburgh among others.

The ultimate premium ‘staycation’ worth over £5,000, the prize includes one Balcony Stateroom for up to four people, with fabulous sea views, all meals, and the Princess MedallionClass experience. 

Competition closes July 8th 2020.

Win a two-night Italian villa stay

One lucky winner and up to 5 of their chosen guests a chance to win a unique and unforgettable luxury experience – staying at the Monvigliero Vineyard Villas in Piedmont.

You’ll spend two nights at the stunning vineyard villas, where you can enjoy a relaxing stay surrounded by Barolo’s breathtaking UNESCO World Heritage vineyard landscape.

Competition ends July 18th 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 a 5 Star Holiday to Crete & £2,000 to Spend at Crew Clothing

To celebrate our new kidswear collection, Crew Clothing has teamed up with Scott Dunn and Daios Cove to whisk you away on that holiday we know you so deserve.

Stay in the lap of luxury for five blissful nights this year or next with all posh-nosh, snacks, ice cream and cocktails covered for two grown-ups and two little ones.

There’s even a Scott Dunn Explorers kids club on-site, so while they’re making best friends, your only worry will be whether you take a long dip in the infinity pool or head down to the secluded private beach.

Competition closes July 30th 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 4-night foodie adventure to Norway

Each year, to mark the March and September equinoxes, and the summer solstice in June, Holmen Lofoten hosts Kitchen On The Edge Of The World, which sees brilliant chefs and bright thinkers of the foodie world come together for a four-day experience of feasting, foraging, fishing and exploring.

The prize-winner and their guest the ropes with a cooking class championing wild food and local, seasonal ingredients. Guests can also hop in a RIB for a fishing trip – March being the annual migration season for the Arctic cod – and enjoy picnics along the banks of the lakes.

Competition closes 13th August 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.