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Holiday Competitions
Life is hard – more so recently than ever! You deserve a break and with these holiday competitions, you will have the chance to win a holiday free of charge!
We have the full range of travel competitions, from short weekend breaks based in the UK to exotic ‘once in a lifetime’ luxury getaways. Going away with the family is an expensive ordeal. With the listings below you can win a family holiday - the opportunity to experience places that you would otherwise only dream of visiting and make lasting memories together.
Holidays and trips are some of the most popular (and valuable!) prizes. Here are all the holiday competitions currently available – run only by reliable and trustworthy websites.
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UK HolidaysYou could win a nine-night stay for two people with Journeyscape, exploring Atlanta, Nashville and New Orleans.
The prize includes accommodation, international return flights with 23kg checked baggage per person, flight from Nashville to New Orleans and car hire in the USA. Simply enter your details below for a chance to win.
In celebration of SUPERGIRL landing in cinemas June 25, you could win a luxury getaway in London PLUS a year's supply of popcorn!
Two nights at the superb Sofitel St James Hotel sets the mood for super girls or boys.
See the skyline of London with a rooftop cocktail and dinner before meandering through the vibrant streets and back to your hotel.
Dreaming of a Greek island escape? We’re giving you the chance to win a luxury getaway for two worth £1,500!
You and a lucky plus-one could be jetting off to the stunning Cabú Adults Only Hotel for the ultimate private, five-star retreat.
- Return flights from the UK + return airport transfers
- 5 nights in a Superior Room at the Cabú Adults Only Hotel
- Daily breakfast included
- Valid for 2x adults (18+)
Sign up to our emails…to be in with a chance of winning £500* off your next TUI holiday. Plus, you’ll be the first to know about our exclusive offers and holiday information.
One lucky Square Mile reader will win an unforgettable three-night, four-day Northumberland expedition courtesy of Overland Adventures, one of the UK's leading luxury Defender adventure specialists.
Your prize includes exclusive use of a fully equipped classic Land Rover Defender 110 and a bespoke Northumberland 250 itinerary designed to showcase the very best of England's most underrated county.
Discover dramatic castles overlooking the North Sea. Cross the tidal causeway to Holy Island. Explore the vast wilderness of Kielder Forest. Enjoy some of Europe's finest stargazing beneath Northumberland's internationally recognised Dark Sky skies.
We’re giving away two cosy two-night stays at Coombe Barn. With space for eight guests across four comfy bedrooms, it’s the perfect spot for a family retreat, catching up with your favourite people, or that long overdue celebration.
There’s adventures waiting right outside the door, so pack your wellies, lace up those walking boots and get ready to make some memories. Fresh air, lots of laughter and questioning “why don’t we do this more often?” pending.
Win a two-night stay for two at The Guardsman in London. The prize includes breakfast.
The Guardsman was made for discerning travellers looking for polished luxury, a suave British vibe and superb setting. It feels very exclusive here; more like a member’s club than a hotel. You’re certainly given special treatment during your stay thanks to the exceptional service, which is extremely intuitive with the aim to provide each and every guest with a memorable, personalised experience in the capital.
Win a four-night stay at Terme Di Saturnia Natural Spa & Golf Resort, including breakfast and access to the championship golf course for two.
Nestled in the unspoilt rolling hills of The Maremma, Terme di Saturnia Resort is a five-star retreat like no other. Here, the healing waters at the world-renowned natural springs and timeless Tuscan charm have long been a drawn for those seeking wellness amid natural beauty, with first-rate cuisine and an award-winning golf course on the doorstep.
Win a two-night stay for two at Hotel Can Simoneta in Mallorca. The prize includes breakfast each morning for two persons and a half board one evening x 2 (drinks not included). Travel is not included in the prize
- A two-night stay
- Breakfast for two
- Half board one evening x 2 (drinks not included)
Win a three-night stay for two people in luxury accommodation at The Monteleone, including bed and breakfast.
One lucky winner will enjoy a three-night stay for two in a Superior Double Sea View Room, complete with a king-size or twin bed, walk-in shower, premium amenities, and a private balcony overlooking the Ionian. The setting lends itself to an easy-going pace, from quiet mornings to evenings spent watching the sunset over the water.
Flights, transfers, insurance and any additional expenses are not included.
A luxury five-star holiday in Greece for two people, including flights.
Plus we have more than £45,000 worth of prizes up for grabs, including products by Sisley, Charlotte Tilbury, NARS, and Dermalogica.
Ready for your next getaway? We’re giving you the chance to win a trip for two to Cincinnati, including return flights, four nights’ accommodation in a four-star hotel, plus £250 spending money!
Ready to spice up your summer plans? We’ve teamed up with Encona to give you the chance to win a £5,000 holiday. Where? Anywhere you like.
So whether you want to escape to somewhere extra hot, or fancy milder temperatures with a dash of local flair and flavour, this is summer’s spiciest giveaway yet.
We've teamed up with Outdoors Magic and Altberg to offer you and your companion of choice a weekend away in the stunning Yorkshire Dales.
Including luxurious accommodation, an Altberg factory tour, personalised boot fittings and a guided hike - what's not to like?
Win a National Trust stay worth up to £500!
We’ve teamed up with National Trust to offer one lucky winner the chance to enjoy an unforgettable stay at a National Trust holiday cottage or campsite!
Metro has teamed up with Starhotels Collezione to give one lucky reader (and a companion) a chance to win a luxurious two-night stay worth £900 at The Gore London, a historic boutique hotel in the cultural heart of the UK capital.
We’re giving you the chance to win a family weekend trip to Chessington World Of Adventures plus Paw Patrol goodies! Entries close 11:59pm on Wednesday 12th August. Good luck!
- One day entry to Chessington World of Adventures, including the World of Paw Patrol.
- Overnight accommodation at Chessington Safari Hotel sharing a family room and including breakfast.
- £200 contribution towards return travel. Above this, transport between home and the venue (and vice-versa) is the responsibility of the Participants.
- £150 contribution towards food and drink.
Become the ultimate Spidey Superhero on an action-packed trip to Berlin with Spider-Man: Brand New Day! Entries close 11:59pm on Wednesday 12th August. Good luck!
Start by pampering your taste buds with a 'foodie break' package at one of the city's most exclusive addresses, The Francis Hotel. As well as an overnight stay in one of the hotel's stylish, individually designed rooms, you'll also be treated to a £150 dining credit in the neighbouring Emberwood restaurant - all you need to do is choose how you'd like to spend it!
- A 'Foodie Break' package for two at The Francis Hotel, including a one-night stay for two people sharing a room and a £150 dining credit to share in the Emberwood restaurant. Valid for stays Sunday - Thursday until 31 March 2027.
- A Swedish or Deep Tissue Massage for two at Manipura House, redeemable for up to 3 months from 12 August 2026.