Win a Holiday

Dreaming of sun-drenched beaches, snowy ski slopes or magical Disney escapes without paying a penny – or even leaving your sofa? You’re not alone. Travel competitions are booming in the UK and offer a real opportunity to turn those daydreams into reality. Whether you want to win a luxury holiday, a spontaneous city break, or an unforgettable family adventure, entering online has never been more accessible – or more rewarding.

This guide shows you how to navigate today’s most promising holiday prizes. From understanding entry types to boosting your winning chances, here’s everything you need to know.

Why Holiday Competitions Are Worth Entering

Holiday competitions offer a unique mix of low entry barriers and high-value rewards, making them an appealing option for anyone with a sense of wanderlust. Participants can choose from a wide range of prize formats – from weekend getaways to full-package experiences such as an all-inclusive holiday. Many competitions are run by established travel brands or specialist raffle platforms like Fifty20, which helps ensure transparency and reliability. With flexible entry models and prizes tailored to different lifestyles and group sizes, it’s no surprise that more and more people are seizing the chance to win a trip. Why not join them?

How Travel Competitions in the UK Work

Holiday competitions typically fall into two main categories: free-to-enter prize draws and paid-entry raffles with limited ticket numbers. In free draws, participants usually enter by sending a postcard, subscribing to a newsletter, or engaging with a social media post – all for the chance to win a trip for free. These are often used by brands to boost visibility or reward loyal audiences.

Paid raffles, on the other hand, allow entrants to purchase one or more tickets, with the promise of higher-value rewards such as luxury escapes or exclusive experiences. In these cases, the number of participants is often capped, which can significantly improve your odds of winning.

Free Entry Doesn’t Always Mean Low Value

Many of the most attractive holiday prizes don’t cost a penny to enter. In fact, free entry competitions are among the most popular formats in digital marketing campaigns – and they still offer the chance to win a free holiday. Although the competition may be steeper due to the large number of entrants, these draws require minimal effort: no purchase, no commitment, just a few clicks. They’re a perfect entry point for newcomers who want to try their luck without financial risk. And for seasoned participants, free entry draws remain a valuable part of any competition strategy.

How to Identify a Legitimate Holiday Raffle

With the rise of online competitions, it's easier than ever to take part in a holiday giveaway – but not every contest you encounter is genuine. Spotting the difference between trustworthy raffles and potential scams is crucial if you want to protect your data and avoid disappointment. Fortunately, there are clear indicators that can help you recognise a legitimate competition. Before entering, take a moment to check for the following:

Clear prize descriptions outlining value, destination, and included services (e.g. flights, accommodation, extras)
Well-defined terms and conditions including deadlines, eligibility, and selection process
Verified organisers with visible contact details or ties to known brands
No requests for sensitive financial data such as bank details
A visible privacy policy outlining how personal data is used