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 trip to Orlando, Florida

To celebrate the 2019 NFL London games, Virgin Atlantic is giving one lucky person the chance to win a trip to Orlando, Florida with three friends to see the 2020 NFL Pro Bowl.

Competition closes on November 3rd 2019.

Win a trip to Los Angeles 

Win a Charlie’s Angels themed trip to Los Angeles with Chambord!
The holiday package shall consist of the following:
  • Two (2) round trip economy airfares between the major international airport closest to winner’s residence and Los Angeles International Airport (LAX), California, USA.
  • Roundtrip transfers from Los Angeles International Airport to the hotel.
  • Room accommodations consisting of one (1) standard room (with a maximum of two (2) persons per room) for three (3) nights at a hotel in Los Angeles, to be selected by the Promoter in its sole discretion;
  • A Charlie’s Angels inspired stunt experience at a stunt training facility in Los Angeles are which shall include:
  • 2-3 hours activity with a professional stunt co-ordinator to feature some or all of the following; fight choreography and hand to hand combat skills and wirework. In addition, you will be taken to an Escape Room facility and experience a 1-hour simulated mission.
  • Round trip transfers from the chosen hotel to the stunt training facility.
  • Round trip transfers from your hotel to an LA Rooftop bar where you will have a bar tab of $100USD

Competition closes November 28th 2019

Win a dream trip for 2020

Fat Tire Tours’ annual Win a Dream Trip Contest is back for its 7th year! Don’t miss out on the chance to win your dream vacation to one of our 12 destinations in the U.S. and Europe for you and a friend! Enter September 30th through October 28th for your chance to win a trip valued at $7k!
    • Round Trip Airfare for Two to the Fat Tire Tours destination of your choice
    • Five Night Stay Accommodation
    • Roundtrip Airport Transfer at your destination
    • UNLIMITED tours with us – Fat Tire Tours!
  • 60-minute photoshoot with Flytographer
  • A Weekender Bag and Essentials Kit from Birdling
  • One year premium subscription to Matt’s Flights

Competition closes October 28th 2019.

Win a holiday for two to Barbados

Enjoy everything the Caribbean has to offer with a holiday for two to Barbados’s Platinum Coast. The lucky winner and their guest will spend seven nights in a one-bedroom ocean-view suite at the premium all-inclusive resort of Crystal Cove. Its amazing beachfront cliff setting, sea views and tropical scenery will take your breath away.

Guests are guaranteed the warmest Bajan welcome, with the prize including all-day dining and drinks. There’s also a beach ambassador service and complimentary motorised water sports.

Competition closes November 12th 2019

Win a trip to Iceland

To celebrate the launch of Ted Baker’s new autumn collection, one lucky winner – and their plus one – will be going on an enchanting 3-night getaway in the Icelandic wilderness.

The prize for one lucky winner includes:

  • Return flights for two from Europe to Reykjavik, Iceland
  • Car hire for the duration of the stay
  • 3 nights accommodation in The Panorama Glass Lodge, Iceland
  • A fully stocked fridge and a hamper from Ted

Competition closes October 21st 2019.

Win a seven-night Cox & Kings tour of Jordan for two

Cox & Kings are offering one reader the chance to win two places on a Splendours of Jordan eight-day/seven-night group tour, including flights.

Cox & Kings signature experiences:

  • Spend two full days exploring Petra and tour the remote ruins of Little Petra
  • 4×4 desert excursion over the dunes in Wadi Rum
  • Time at leisure to enjoy the mineral-rich waters of the Dead Sea

Competition closes on November 17th 2019.

Win a ski holiday to Niseko in Japan 

Skye Niseko, Finnair, Experience Niseko and a host of other sponsors are partnering again to present Niseko’s biggest winter giveaway!

Simply enter and you could win the following:

  • 2 x return economy airfares flying Finnair from any airport in Europe which Finnair operates, to Sapporo (New Chitose Airport) via Helsinki
  • A 7-night stay for two people in a Skye Niseko one-bedroom suite including daily breakfast at Kumo Restaurant
  • 6-day Grand Hirafu lift passes for two people
  • 6-day GoSnow group ski/snowboard lessons for two people
  • 6-day premium ski/snowboard rental equipment from YamaSport
  • 2 x 60-minute Deep Tissue massages at Ryko Spa
  • Return airport transfers for 2 people
  • Dinner for two people at Kumo Restaurant to the value of ¥20,000

Competition closes on November 30th 2019.

Win an enchanting stay at The Witchery in Edinburgh

Travel Scoop giving you the chance to win an enchanting night away at The Witchery by the Castle in Edinburgh

The prize

  • 1 night stay in a suite at The Witchery by the Castle with oodles of glamour, indulgence, luxury and roll-top baths for two
  • Welcome bottle of Champagne
  • Full Scottish breakfast

Competition closes on October 28th 2019.

Win a luxury holiday to Oman

One lucky family will be jetting off to the sunny, exotic shores of southern Oman with Oman Air to stay at the luxury Al Baleed Resort Salalah by Anantara.

The Prize:

  • Travel for a family of four (2 adults and 2 children under 18)
  • 7 nights in a One Bedroom Garden View Pool Villa including lunch and dinner for four
  • Private dolphin spotting boat trip
  • Cinema Under the Stars experience
  • Half-day tour with Salalah Guru including scenic gourmet picnic lunch
  • Roundtrip transfers
  • Round trip economy flights from London/Manchester to Salalah
  • Prize value: £8,420

Competition closes on November 4th 2019.

Win 8 day holiday to New Zealand

For your chance to win a holiday to New Zealand including flights, all you have to do is answer a simple question. Competition closes on October 20th 2019.

Win a 3-night trip to Rome

Hands up who’d like to a win a 3-night luxury break in Rome staying in a glamorous apartment just a coin’s throw from the Trevi fountain? Knomo has teamed up with our friends at i-escape, who offer a hand-picked collection of the best boutique hotels, B&Bs and villas worldwide. You and a friend could be jetting off to Rome for the perfect city adventure. Competition closes on October 20th 2019.

Win a luxury honeymoon in Indonesia worth £11000!

One lucky winning couple will spend four nights in paradise in one of Bawah’s stunning Overwater Bungalows. Accessed by wooden walkways, the bungalows have panoramic views over the lagoon and outer islands and come complete with a private verandah and open-air sundeck with steps straight into the tropical waters below. Competition closes on November 7th 2019.

Win a trip for 2 to New Zealand

Thanks to STA Travel, one person will win a trip for 2 people in New Zealand with Kiwi Experience. This includes: return flights from London in economy class to the value of £800 each only and a Whole Kit and Caboodle Kiwi Experience pass worth a value of £966 each. Competition closes on October 31st 2019.

Win a trip to Boston

For the ultimate Yankee Candle experience, enter the prize draw to win a trip to Boston, including a day trip to Yankee Candle factory and flagship store. Competition closes on December 11th 2019.

Win a 7 night luxury holiday to Grenada

National Geographic Traveller (UK) has teamed up with Sandals Resorts to offer the ultimate escape to Grenada.

The winner and their partner will receive seven nights at Sandals Grenada Resort & Spa for two adults, return economy flights from Gatwick and resort transfers. Sandals Grenada Resort & Spa is a Luxury Included resort, which means the lucky pair can enjoy all-inclusive, five-star global gourmet food as well as unlimited top-shelf premium spirits and fine wines for the duration of their stay. Competition closes on October 31st 2019.

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 holiday to The Maldives 

Conde Nast Travellers are giving away a five-night stay at Coco Bodu Hithi, a smart escape on the beautiful North Malé Atoll in the Maldives. Also included in the prize is a sunset cruise aboard one of Coco Bodu Hithi’s hand-crafted coconut-timber dhoni sailboats, as well as a couple’s treatment in the overwater spa.

The hotel also offers jet-skiing, powerboating, big-game fishing and wakeboarding, as well as yoga at sunrise and sunset on the pavilion, surrounded by panoramic views of the lagoon. Competition closes on November 3rd 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.

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 couples holiday to Majorca

One lucky winner will win a holiday to Majorca for two people, which will consist of the following; return economy flights from a UK airport to Palma, 7 nights accommodation staying in a 4-star hotel and return overseas transfers. Competition closes on 31st December 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 a 7 night holiday to Tobago 

Enter the prize draw for the chance to win an incredible trip to Tobago with return flights from London Gatwick with British Airways. Competition closes December 31st 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.