Can You Really Win Holiday Competitions?
You may have read our original version of this post, written back in 2025. Well, the world of holiday competitions moves quickly, new platforms appear, clever new entry methods pop up, and the tricks that worked brilliantly last year sometimes need a little dusting off. So we have rewritten this guide from scratch for 2026 to make sure everything you read here is as fresh and useful as possible.
Now, to answer the big question: can you really win? Absolutely, yes. And before you roll your eyes and mutter something about lightning and thunderstorms, hear us out. We are living proof that real people win real holidays, because we have done it ourselves. Not once, but two fabulous holiday wins. Proper, pinch-yourself, check-your-spam-folder-three-times wins!
Holiday competitions offer the chance to win a free holiday explore stunning destinations, indulge in luxurious stays, and create utterly unforgettable memories, all without touching your savings. Of course, with thousands of eager hopefuls entering the same draws, you will need a bit more than blind luck to land the big one.
Fear not – we’ve got the insider tips you need to help maximise your chances!
Your Quickfire Guide to Winning Holiday Competitions
- Enter, enter, enter – You cannot win if you do not enter. This is not a drill.
- Pick prizes you actually want – If you get seasick on a pedalo, perhaps skip the transatlantic cruise.
- Follow the rules – Read the small print, check the deadlines, and tick every single box. Competitions are frequently won because others did not bother.
- Go for the quirky comps – Anything with extra entry requirements tends to put people off. Their laziness is your advantage.
- Quality over quantity – Entering dozens of well-chosen competitions thoughtfully will serve you far better than blasting through hundreds using autofill. Focus beats volume, every time.
- Use a dedicated email address – Keep your personal inbox clutter-free and your competition life gloriously organised.
- Get creative – If a competition asks for a photo, a short video, or a witty slogan, go the extra mile. Judges adore originality and quietly despise the mediocre.
- Be wary of social media comps – The odds are frequently brutal, and scammers lurk like seagulls at a chip shop on the prom. Always verify before you click anything.
- No win is too small – Every smaller prize builds your comping confidence. Today’s weekend break could lead to next year’s fortnight in the Maldives.
- Stay positive – Persistence is the real secret weapon. Keep going, even when it feels entirely hopeless.
Where to Find the Best Holiday Competitions
Start by bookmarking the Rosemary and Pork Belly holiday and travel competitions page. We sift through the internet’s endless noise so you don’t have to, filtering out the dodgy, the dubious, and the outright weird.
Better yet, sign up for our fortnightly newsletter, where we spotlight six handpicked top-notch competitions that we actually think are worth your time. No padding, no filler
Other good hunting grounds include:
- Search online – Terms like “win a holiday 2026” and “holiday competition UK” are your friends. Keep searches fresh and dated.
- Follow brands on social media – Airlines, hotels, tour operators, and tourism boards regularly run giveaways across Instagram, Facebook, Bluesky, Threads and TikTok. A quick follow today could be a boarding pass tomorrow.
- Subscribe to newsletters – Many travel brands reserve exclusive competition entries for their subscribers. It costs nothing and your inbox has seen worse.
- Attend travel shows – The Telegraph Travel Show, Holiday World, and various regional expos often feature on-site raffles and giveaways. You might even enjoy them.
- Check food and product packaging – On-pack competitions are everywhere if you look, on your breakfast cereal, your coffee jar, your bottle of ketchup. Purchase-necessary competitions often attract a fraction of the entrants of a free online draw. Keep your eyes open in the supermarket aisle.
- Complete legitimate online surveys – Some reputable survey sites offer competition entries as rewards. Emphasis on reputable. Google them first.
- Check loyalty programmes – Many airlines and hotel groups now include prize draws within their rewards schemes. If you are collecting points anyway, you might as well enter the draws.
- Watch TikTok live giveaways – An increasingly popular competition platform, TikTok runs live draws where winners are chosen at random by the platform itself. Worth keeping an eye on, particularly from travel brands
- Look for local business competitions – Small local businesses, restaurants, venues, boutique hotels, and shops run competitions that attract a tiny fraction of the entries of national ones. Facebook and Instagram are the best places to find them, and the odds are delightfully encouraging.
Always check the terms and conditions before entering, and always make sure the competition is legitimate. If something feels off, it probably is.
Smart Tips for Entering in 2026
- Enter only what suits you – Most prizes are non-transferable, which means you cannot flog the holiday, swap it for cash, or hand it to your sister. If the dates are impossible or the destination sends you into a cold sweat, move on.
- Make a competition wishlist – It sounds delightfully organised, but writing down the kinds of prizes you actually want, from a weekend UK break all the way up to a long-haul dream trip, keeps your focus sharp and stops the hobby feeling overwhelming. You can then match competitions to your wishlist rather than entering everything willy-nilly.
- Read the terms and conditions – Some competitions require winners to share photographs or feature in marketing. If the thought of appearing in a brand’s Instagram Reel fills you with existential dread, factor that in before entering. Every UK prize promotion is legally required to have terms and conditions, and a quick read before you enter could save a world of disappointment later. Although some are badly written they should tell you exactly what is and is not included for example are flights covered? Is travel insurance thrown in? Are there blackout dates conveniently covering every school holiday? Can you bring who you like? These are not small details. And if a competition has no visible Ts&Cs at all be more cautious. Reputable promoters have nothing to hide.
- Go for effort-based competitions – Competitions requiring a photo, a slogan, or a short video have significantly fewer entrants. People are fundamentally lazy, and that laziness is your golden opportunity.
- Try entering overnight for instant win competitions – If a competition uses a “winning moment” format, where a specific moment in time is pre-selected as the winning entry, entering during quieter overnight hours means you face far less competition for those precious windows. Set a reminder, have a biscuit, enter in your pyjamas.
- Watch out for AI-generated entries – In 2026, many competition organisers running creative competitions are becoming wise to AI-written slogans and obviously artificial submissions. Your genuine wit, personality, and charm remain your best assets. Let them shine.
- Prioritise competitions closing soon – A competition with two days left and fewer people aware of it is a far more attractive prospect than one with six weeks to run and a growing entry pile. Keep an eye on closing dates and pounce accordingly.
- Keep a competition diary – A simple spreadsheet noting what you entered, when, and any deadlines works wonders. You will thank yourself when a winner notification lands and you cannot remember entering anything in the past three months.
Frequently Asked Questions About Holiday Competitions
Do free online entries ever win?
Yes, genuinely. Many competitions offer free entry routes alongside paid options, and under UK regulations, free entries must be given an equal chance of winning. Our extraordinary holidays came without spending a penny in entry fees. The playing field is far more level than you might think.
Is it safe to enter holiday competitions in 2026?
Generally yes, but caution remains your best friend. Stick to reputable websites and well-known brands. Check privacy policies before submitting any personal details. Ensure your device has up-to-date antivirus protection, and never, ever click on links that arrive in unsolicited messages claiming you have won something you did not enter. The golden rule: if it seems too good to be true, it invariably is.
How can I tell if a holiday competition is legitimate?
There are several reliable checks:
• Check whether the competition is hosted by a well-known company or a reputable competition site.
• Look for clear terms and conditions, including entry deadlines, prize details, and a closing date.
• Be wary of competitions that demand excessive personal information or payment before you can claim a prize.
• Search the competition name alongside the word “scam” and see what comes up.
• Check the brand’s official website or social media to confirm the competition is real
Will entering competitions lead to spam emails?
It depends entirely on where you enter. Use a dedicated email address for all competition entries. Only opt into newsletters when it is a genuine entry requirement. Read privacy policies before submitting your details. Legitimate companies will always let you unsubscribe without drama.
Should I pay to enter holiday competitions?
In general, no. Some paid competitions legitimately donate proceeds to charity, which is a different matter entirely, and free entries should always carry equal odds. If a competition pressures you to pay in order to improve your chances of winning, walk away. That is not how genuine competitions work.
Are social media competitions worth entering?
They can be, though the odds are often sobering given the sheer volume of entrants. The landscape has also shifted somewhat, with platforms like Bluesky, Threads, and TikTok joining the familiar faces of Instagram and Facebook as competition venues. TikTok live draws in particular are worth watching, as winners are selected randomly by the platform itself, making them genuinely fair. Be cautious of fake giveaways, which continue to proliferate. Genuine competitions will never ask for your banking details, direct you to suspicious links, or require you to send money to release your prize.
How often should I enter to increase my chances of winning?
As often as reasonably possible, but quality matters as much as quantity. Making it a daily or weekly habit and keeping a record of your entries helps you stay organised, avoid duplicates, and remember to check for winning notifications.
What happens if I win a holiday competition?
First things first: do not assume the email is genuine without checking. Verify the win by cross-referencing the notification with the original competition and its terms and conditions. Be prepared to provide any requested details promptly, as most competitions have tight deadlines for claiming prizes. Check carefully for any additional costs, such as travel insurance, airport transfers, or meals, which may not be included. Confirm travel dates before accepting, and then allow yourself to feel wonderfully smug about the whole thing.
Can I transfer my prize to someone else if I cannot go?
Almost certainly not. Most holiday prizes are non-transferable, which means you cannot pass them along to a friend, a family member, or sell them on. Always check this before entering, particularly if your diary is the sort of thing that requires a military-grade planning operation.
Are effort-based competitions easier to win?
Considerably so. Competitions requiring a photo, a short video, a slogan, or an essay attract a fraction of the entrants of a simple prize draw. Put genuine effort into your submission, because it genuinely counts. Before the internet was a twinkle in anyone’s eye, we once won a television by writing a small poem for a slogan competition. The effort paid off handsomely. We have also slaved over what we considered a perfect slogan and won an oven glove. That is the game, and we love it.
What’s the best holiday competition site in the UK?
We are biased, naturally, but Rosemary and Pork Belly is your best starting point for handpicked, trustworthy, and genuinely winnable travel competitions. We sift through the internet’s considerable offerings to bring you the most exciting and credible giveaways, whether that is a luxury beach escape, a thrilling adventure break, or a charming UK staycation. Our list is regularly updated, so if it is worth entering, it will be on our site.
Here are a few websites and forums we trust
SuperLucky Di – is packed with news on the latest competitions, along with genuinely useful hints and tips on boosting your chances. Di is a seasoned winner herself and her advice is well worth heeding.
The Prizefinder is a user-generated forum we have found reliably useful for sourcing good competitions, particularly for finding those about to close that you might otherwise have missed.
Moneysaving Expert – is another reliable community resource. Create a profile and you can use the search tools to surface competitions that match your interests. Very handy for closing-soon alerts.
The Joy of Winning
Winning a holiday competition is, frankly, pure magic. The disbelief, the elation, the urgent need to tell absolutely everyone you know, it is an experience you will not forget. Your first reaction will almost certainly be “I do not believe it”, which is precisely the right reaction.
Always verify that you did actually enter, with that company, before doing anything else. Never click on suspicious links. Once you are satisfied that everything is completely above board, soak up the moment. You have earned it.
If the original terms and conditions have disappeared from the organiser’s website by the time you come to claim, it is perfectly reasonable to ask them for a copy to remind yourself what is included in the prize. Most reputable companies are happy to oblige.
What have Rosemary and Pork Belly won?
We’ve been entering travel competitions on and off for many years and have had two spectacular, amazing and glorious holiday wins.
The first was a family holiday to Universal in Orlando, Florida – complete with Hard Rock Hotel, theme park tickets, and fast passes. And here is a cautionary tale to file away: we nearly did not enter. Rosemary chucked the entry form which meant I had to rummage through the bin to rescue it. Smoothing out the crumples, I went ahead and entered. Moral of the story: never dismiss an entry as pointless. One entry is infinitely better than no entry.
The second was a trip to Antigua, staying at Blue Waters Resort.
We have also enjoyed several smaller UK travel wins, the highlight being a trip to Padstow for the Christmas Festival – three days of eating, drinking and demonstrations. Absolutely no hardship whatsoever.
As for what comes next? We are still entering, still dreaming, and still checking our emails with rather more excitement than is probably healthy.
Your Turn
Have you cracked the code for holiday competition wins? Have a tip, a cautionary tale, or a glorious win story of your own? Pop it in the comments below. The dream holiday could genuinely be just one entry away, so what on earth are you waiting for?
All photographs taken while enjoying a competition win copyright ©rosemaryandporkbelly
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