How to win holiday competitions in 2025

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Blues Brothers Universal Studios, Orlando ©rosemaryandporkbelly
win holiday competitions

Can You Really Win Holiday Competitions?

Absolutely – we’re living proof. We’ve bagged not one but two fabulous holiday wins, and let us tell you, the thrill of a “Congratulations, you’ve won!” email is a feeling like no other.

Holiday competitions offer the chance to explore stunning destinations, indulge in luxurious stays, and create unforgettable memories – all without opening your wallet. But let’s be honest, with thousands of eager entrants, you’ll need more than a sprinkle of luck to bag a win.

Fear not – we’ve got the insider tips you need to help maximise your chances!

Blue Waters Resort, Antigua © rosemaryandporkbelly.co.uk
Blue Waters Resort, Antigua

Your Quickfire Guide to Winning Holiday Competitions

  • Enter, enter, enter – You can’t win if you don’t enter. Simple.
  • Pick prizes you actually want – If you get seasick, why enter for a cruise?
  • Follow the rules – Read the fine print, check deadlines, and tick every box.
  • Go for the quirky comps – Ones with extra entry requirements often have fewer competitors.
  • Use a dedicated email – Keep your personal inbox clutter-free.
  • Get creative – If a comp asks for a photo, video, or witty slogan, go the extra mile. Judges love originality.
  • Be wary of social media comps – Huge numbers enter, so the odds are low. Scammers may encourage users to follow fake accounts and enter fake draws.
  • No win is too small – Every success is a step closer to the big one.
  • Stay positive – Persistence is key. Today’s loss could be tomorrow’s jackpot.

Where to Find the Best Holiday Competitions

Start by bookmarking our holiday and travel competitions page. We filter out the dodgy ones so you don’t have to!

Better yet, sign up for our fortnightly newsletter, where we spotlight six top-notch comps, handpicked just for you.

Want more?

  • Search online – Try terms like “win a holiday” and “holiday competition.”
  • Follow brands on social media – Airlines, hotels, and tour operators love a good giveaway.
  • Subscribe to newsletters – Many travel brands offer exclusive comp entries.
  • Attend travel shows – These often feature raffles and giveaways.
  • Complete online surveys – Some legitimate survey sites offer comp entries as a reward.

Always check the terms and conditions before entering, and make sure the competition is legitimate!

Exterior of the Hard Rock Cafe Universal theme parks Orlando Florida
Hard Rock Cafe Universal theme parks Orlando, Florida

Smart Tips for Entering

  • Enter only what suits you – Prizes are often non-transferable, so if the dates or destination don’t work for you, move on.
  • Check terms carefully – Read the T&Cs. Some comps require winners to share photos or stories for marketing. If that’s not for you, skip it.
  • Go for effort-based comps – Fewer people enter comps requiring skill or creativity, increasing your odds.

Frequently Asked Questions About Holiday Competitions

Do free online entries ever win?

Yes, absolutely! Many competitions offer free entry alongside paid options, and under UK regulations, free entries must be treated equally. We’ve won amazing holidays without spending a penny.

Is it safe to enter holiday competitions online?

Yes, but you need to be cautious. Stick to reputable websites, check privacy policies, and avoid competitions that seem too good to be true. Ensure your device has up-to-date antivirus protection and never click on suspicious links.

How can I tell if a holiday competition is legitimate?

Check if the competition is hosted by a well-known company or reputable competition site.
Look for clear terms and conditions, including entry deadlines and prize details.
Beware of competitions that ask for excessive personal details or payment to claim a prize.
Google the competition name along with “scam” to see if others have flagged issues.

Will entering competitions lead to spam emails?

It depends on where you enter. To manage this:
Use a dedicated email for competitions.
Only opt into newsletters if required.
Read privacy policies before submitting details.
Legitimate companies should let you unsubscribe easily.

Should I pay to enter holiday competitions?

In general, no. Some paid competitions donate proceeds to charity, but free entries should have an equal chance of winning. If a competition is legitimate, it won’t pressure you to pay to improve your chances.

Padstow Christmas Festival chefs © rosemaryandporkbelly.co.uk
Meeting the chefs at Padstow Christmas Festival

Are social media competitions worth entering?

They can be, but your odds of winning are often lower due to high entry numbers. Also, be wary of fake giveaways – genuine competitions will not ask for banking details or direct you to suspicious links.

How often should I enter to increase my chances of winning?

As often as possible! The more competitions you enter, the better your chances. Make it a daily habit and keep a record of entries to avoid duplicates.

What happens if I win a holiday competition?

Once notified, verify your win by checking the competition’s original terms and conditions. Be prepared to provide any requested details, and check if there are any hidden costs (e.g., travel insurance, meals). Always confirm travel dates before accepting.

Can I transfer my prize if I can’t go?

Most holiday prizes are non-transferable, meaning you can’t pass them to someone else or swap for cash. Always check before entering if the dates and destination work for you.

Are effort-based competitions easier to win?

Yes! Competitions that require a photo, video, slogan, or short essay often have fewer entries, giving you a much better chance. Put some effort into your submission – it could be your golden ticket! In the days before the internet, when slogans were the popular way to enter a comp, we won a TV because we took the time to work up a little poem. Mind you, we once slaved over a perfect little slogan and won … an oven glove!

What’s the best holiday competition site in the UK?

Looking for the best, handpicked holiday competitions? Rosemary and Pork Belly is your go-to source. We sift through the internet’s endless competitions to bring you the most exciting, trustworthy, and winnable travel giveaways. Our regularly updated list ensures you never miss a chance to bag a dream getaway, whether it’s a luxury beach escape, a thrilling adventure holiday, or a cosy UK staycation. If it’s worth entering, you’ll find it on our site!

Islands of Adventure Orlando Florida ©rosemaryandporkbelly
Islands of Adventure, Florida

Here are a few websites and forums we trust

SuperLucky Di – packed with news of the latest comps and hints and tips on the best way to increase your chances. Di is a BIG winner herself and her advice is worth heeding.

The Prizefinder, and Moneysaving Expert – these are user-generated forums which we’ve found to be reliable and useful in sourcing good competitions. Create a profile, and you can use the power of algorithms (or gorilla-rithms as Pork Belly calls ’em) to serve up competitions that match what you’re looking for. Also, very good for finding ‘closing soon’ comps you may have missed.

Universal Studios Theme Park Florida ©rosemaryandporkbelly
Universal Studios, Florida

And finally ….

The Joy of Winning

Hard Rock Hotel Orlando Florida ©rosemaryandporkbelly
Hard Rock Hotel, Orlando – our family home for 7 days!

Winning a holiday competition is pure magic. The disbelief, the elation – it’s an experience you won’t forget.

Your first reaction will be, ‘I don’t believe it!’ And that’s exactly the right way to respond.

We always verify that we actually entered, with that company.

Never click suspicious links. Once you’re satisfied everything’s above board, soak up the moment – you’ve earned it!

If the terms and conditions of the comp are no longer on their website, try asking for a copy so you can refresh your memory of what they’re offering.

Then relax and enjoy your win!

The Snow Queen and Jack Frost, Padstow © rosemaryandporkbelly.co.uk
Padstow Christmas Festival

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.

One was a family holiday at Universal in Orlando, Florida – Hard Rock Hotel, theme park tickets and fast passes.

And here’s a cautionary tale – we nearly didn’t enter!

I’d seen the leaflet and thought, ‘Nah, not a chance’ and popped it in the recycling. Pork Belly salvaged it, smoothed out the crumples, and went ahead and entered.

So never say never – one entry is better than no entry.

The other was our trip to Antigua, staying at Blue Waters Resort.

We’ve also had a few smaller UK travel wins, the best one a trip to Padstow for their Christmas Festival – 3 days of eating, drinking and demonstrations.

And Next?
Well, we’re still entering, still dreaming.

Your Turn
Have you cracked the code for holiday wins? What are your top tips? The dream holiday could be just one entry away – so what are you waiting for?

Men in Black ride Universal Studios ©rosemaryandporkbelly
MIB at Universal Studios, Florida

All photographs taken while enjoying a competition win copyright ©rosemaryandporkbelly


Where to next?
Holiday and Travel Competitions
Dog-friendly holiday cottages UK
A guide to the Prosecco Road

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