Holiday Competitions

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

lady sitting on cliff edge in jersey

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.

The newest travel competitions will be at the top of the page and will be updated with new holiday competitions weekly.

May the odds be ever in your favour!

Win a holiday to America’s most famous music cities

Escorted touring specialist Collette is giving one lucky reader the chance to win an incredible tour of America’s major music cities, featuring Nashville, Memphis and New Orleans! Competition closes Saturday 17th November 2018.

Win a luxury 2 week trip to the British Virgin Islands 

One lucky entrant will win a luxury two-week holiday for two to the BVI including flights from the UK, a week’s sailing with Dream Yacht Charter and a week in Turtle Bay Villa on beautiful Virgin Gorda. Competition closes Wednesday 5th December 2018.

Win a trip for 2 to Costa Rica

Curious about Costa Rica? Rickshaw Travel is giving you are the chance to win a 10 day trip for two to Costa Rica complete with accommodation and excursions.  Competition closes Friday 30th November 2018.

Win an 8 day Christmas Cruise for 2

To celebrate Goadsby’s 60th anniversary they are giving away their biggest and best prize yet…an 8 night Christmas Market Cruise to Germany and Denmark for 2 adults. Competition closes Friday the 9th of November.

Win A Four Star Amsterdam City Break

Win this Dutch getaway for two adults, complete with a four-star hotel for three nights plus flights. It’s a quick hop across the North Sea for the perfect trip for yourself and a loved one. Competition closes 30th September 2018.

Win a Holiday to Austin, Texas

Visit Austin is giving you and a friend the chance to win the holiday of a lifetime to Austin, Texas, in association with Norwegian. Spend 5 nights in the Live Music Capital of the World and take in a gig at the famous ACL Live venue! Competition closes September 30th

Win a trip for two to Venice, Italy 

Win a trip to Venice with Aperol Spitz to visit the home of Aperol. Competition closes October 1st.

Win flights to Dubai from Stanstead airport 

To celebrate the new Emirates flight path between Stanstead airport and Dubai, Bright Sun Travel is giving you the chance to be one of the very first on the new direct route. Competition closes October 5th.

Win flights to Florida, Orlando 

Norwegian are giving you the chance to win a pair of return economy flights to your favourite city in the Sunshine State. Choose from Tampa, Miami-Fort Lauderdale or Orlando on the Boeing 787 Dreamliner. Competition closes January 1st 2019

Win a trip to Disneyland Paris 

The grand prize is a two night, three-day trip to Disneyland® Paris this December for you and up to three guests. Return transport and accommodation will be provided, along with tickets for Disneyland Park and Walt Disney Studios. Continental breakfast, vouchers for an evening meal on Friday and evening dinner on Saturday are also part of the prize. Competition closes October 1st

Win a Candian Rockies tour for two 

Want to discover the soaring peaks, crystal-clear glaciers, iconic wildlife and spectacular national parks of the Canadian Rockies? Enter the prize draw and you could experience this breath-taking scenery for yourself. Spot grizzly bears in Banff and Jasper National Parks, wander the pretty green spaces of Victoria and stay overnight in thrilling Vancouver. Competition closes October 10th

Win an Isle of Wight holiday worth over £2000

Isle of Wight tourism have got together with Classic Cottages and are making a big push on promoting the Island as a great holiday destination.  The prize includes accommodation, travel, as well as activities and some meals. Competition closes on Friday 30th November 2018

Win a holiday to South Africa 

Win a trip of a lifetime to one of my favourite countries – South Africa! This includes a 14-day itinerary along the Garden Route includes a safari at the Addo Elephant National Park and Wine tasting in Cape Town. Competition ends November 23rd 2018.

Holiday 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.

Use your creative to win a walking holiday in Germany

What is your interpretation of a slow moment? Take a photo, put pen to paper, or record a short video and share it to be in with a chance of winning an InnTravel trip. Be as imaginative as possible to stand out. The competition runs monthly with the overall winner being selected in January 2019.

Win two Eurostar tickets to Amsterdam

Win travel tickets to Amsterdam courtesy of King’s Cross, all you need to do is fill out your details. Competition ends September 29th 2018.

Win an all-inclusive adventure holiday to Whistler, Canada. 

This prize looks incredible, and I urge everyone to enter this one. As well as flights and accommodation, Whistler tourism is also including so many different incredible activities during your time there. All you need to do is fill out your details. Competition ends September 27th 2018.

Win a city break to Tallinn, Estonia 

Win a 4 night holiday to Tallinn, including return flights, accommodation and an excursion trip for your chance to see wild bears. All you need to know is how many years of independence Estonia is celebrating in 2018. Competition ends on September 30th 2018.


Remember to check back weekly for new competitions and if you win anything, please do let me know!