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Travel & Holiday Competitions 2021 – Updated Weekly!

Do you want to win your next holiday? Here is my weekly round-up of the best 2021 travel competitions.

I am a big advocate for entering holiday competitions to try to win a holiday. 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 travel competitions you enter, the more chance you have.

Holiday competitions 2021:

The newest travel competitions will be at the top of the page and will be updated with new holiday competitions every other day, so be sure to bookmark this page and keep checking back.

Please note, due to my location, most competitions will be for UK applicants, however, check the competition terms and conditions to be sure.

May the odds be ever in your favour!

Win a one-week stay for two in Sardinia’s new Cascioni Eco Retreat

Win a seven-night stay for two people on a bed and breakfast basis and including all flights and transfers, to Sardinia’s new Cascioni Eco Retreat.

Competition closes February 4th 2021

Win a luxury holiday to Jamaica

Boots have teamed up with Sandals to offer one lucky Health & Beauty reader the chance to win an all-inclusive, seven-night trip for two people to the Sandals South Coast Resort in Jamaica.

Closes April 20th 2021

Win a Holiday for Four on the Le De R with Sunlia Vacances

The prize is a week’s stay on the fashionable island hideaway on France’s Atlantic Coast with accommodation for up to four people in a well-equipped two-bedroom cottage at the island’s top 5* holiday park.

Competition ends February 10th 2021

Win a Luxury Stay for Two in Falmouth

The winner and a guest of their choice will enjoy two nights in the sumptuous Lookout Suite, cocktails on arrival, a Cornish breakfast each morning, a three-course dinner on one evening, a Cornish cream tea, two drinks in The Working Boat pub, and late check-out.

Closes for entries on February 28th 2021

Win a little island break for four in Jersey

We all need a little something to look forward to, so we’re giving you a chance to WIN an island break for two to Jersey for when you can visit us again! Enter now for your chance to WIN and when you can, restore your perfect balance here.

Competition ends of March 31st 2021

Win a Spa Break for Two in Northern Ireland worth £1740

One lucky reader will win a stay for two nights in a suite for two people at Slieve Donard Resort & Spa in Northern Ireland. Our winner will also receive two ‘spatisserie’ treatments, including a spa treatment and afternoon tea.

Competition ends February 28th 2021

Win the Chance to Work from a Corfu Villa for a Month

You and a friend will be able to live and work from Corfu villas for free, and they even cover your flights*. To enter for the chance to win, simply fill in the form on the link detailing why you think you deserve a luxurious home office for a month.

Closes 21st February 2021

Win a £500 Golf Break Voucher

  • Valid for any booking with Findagolfbreak.com
  • Valid for any booking, anywhere in the World
  • Can be given as a gift or prize
  • Valid for new bookings only

Competition ends January 31st 2021

Win a two week holiday to Mauritius

Neutradol are giving away a week for two in Mauritius with flights and transfers.

The prize includes:

  • Return flights from the nearest available major airport to Mauritius
  • Transfers
  • 7 nights in a double room on a half board basis at the Coin de Mire Attitude

Competition closes January 7th 2021

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.

Win a family holiday to New Zealand worth £13,700

Family Traveller has teamed up with VIVID Travel to offer one lucky family the chance to win an incredible 17-day adventure around New Zealand worth £13,700.

Prize includes:
  • Return economy international flights from London Heathrow with Singapore Airways
  • Economy domestic flights
  • All accommodation throughout (mix of room-only and breakfast-included)
  • Transfers from Auckland airport on arrival
  • Car hire
  • All tours and admissions stated including Sky Tower admission, day tour of Coromandel Peninsula, Hobbiton Movie Set Tour, Rotorua Sights and Skyline Gondola Tour, Waitomo Caves tour, Shotover Jetboat Ride, scenic flight to and from Milford Sound, Milford Sound Nature Cruise, and Safari of the Scenes tour

Win a Family Stay At Legoland

Legoland is giving one lucky winner the opportunity to shape the world of LEGO® MYTHICA forever and have their very own mythical creature brought to life on an EPIC scale and featured in our brand new land.

This AWESOME prize includes:

  • Your mythical creature brought to life as a 6ft tall LEGO model, presented pride of place in the heart of the new land
  • Place the final LEGO brick of LEGO® MYTHICA, in a once in a lifetime unveiling ceremony
  • Overnight stay at one of our LEGOLAND Windsor Resort Hotels
  • Premium LEGOLAND Annual Pass for a family of up to 5
  • LEGO Goodie Bag

Closes January 31st 2021

Holiday competition tip: For email entries, draft and save a template email with your name, email, address and telephone number, so you can fire it off quickly. Remember to leave a space for the answer.

Win a Luxury Five-Star Hotel Stay with England’s Coast

Enjoy a one-night stay at Seaham Hall for two people staying in a Junior Suite, including two-course dinner in The Dining Room, breakfast and Spa access (treatments at additional cost), worth £385.

Competition ends January 29th 2021

Win 7 Nights for 2 People Staying at Hotel Elite 3

In The Snow have partnered with Crans Montana to bring you this amazing competition: WIN 7 nights for 2 people staying at Hotel Elite 3*.
Stay in a double room with a mountain view and breakfast included. We will even throw in transfers to and from Sierre train station. It also includes eligibility to Hotelpass.

Please note travel is not included.

Closes January 31st 2021

Comping tip: Comping, if done right, can be a really lucrative as well as fun hobby. While a big part of it is done to luck, you can also increase your chances of winning big if you know what to do.

If you are planning on making comping a hobby then I recommend investing in the Super Lucky Secrets book by Di Coke (currently available in paperback and E-book). Di has bagged over £300,000 of prizes by entering prize promotions – and now you can read a hundred of her tried and tested tips on being a successful winner.

Win a holiday to Turkey

Enter the prize draw today and you and your family could be jetting off this summer for an all-inclusive sunshine holiday to Kusadasi in Turkey with Jet2holidays.

The prize includes 7 nights at the 4-star CLC Kusadasi Golf & Spa Resort plus return flights for up to 2 adults and 2 children.

Competition closes January 31st 2021

Do you want to win a holiday in 2020? A reguarly updated list of all the latest holiday competitions and travel competitions.

Win a Trip Abroad – International Travel Sweepstakes List

Win Trips to Europe, Canada, Asia, and Other International Destinations

Would you like to win a trip abroad? The International Travel sweepstakes list is full of chances for you to win trips overseas. If you want to take a free trip to Italy, the Caribbean, Canada, or other locations outside of the US, this is the place to start. Win free international travel with these sweepstakes!

If you’re looking for chances to win trips within the US, visit the US Vacation Sweepstakes list, or try to win trips to popular destinations with the Hawaii Sweepstakes List and the Las Vegas Sweepstakes List. You can also win free Disney vacations with the Disney Sweepstakes list. If you’d like to win a free cruise, visit the Cruise Sweepstakes list.

1. Bridal Guide – Fashion Survey Sweepstakes
Get the chance to win a five-night getaway for two people to the Conrad Punta de Mita resort in Mexico, a prize valued at over $3,300.
Entry Frequency: Unspecified
End Date: January 18th, 2021
Eligibility: Open to the U.S.
More Information about this Sweepstakes
Enter Sweepstakes Directly

2. Travelzoo – Tripmasters.com Sweepstakes
Enter to win a nine-night trip for two people to Thailand.
Entry Frequency: One time per person
End Date: January 31st, 2021
Eligibility: Open to the U.S. (void in HI & AK)
More Information about this Sweepstakes
Enter Sweepstakes Directly

3. American Way – AAdvantage Miles Sweepstakes
This sweepstakes is giving away up to 25,000 American Airlines AAdvantage miles.
Entry Frequency: One time per person
End Date: March 31st, 2021
Eligibility: Open to the U.S.
More Information about this Sweepstakes
Enter Sweepstakes Directly

4. Sandals Resorts – Sandals and Beaches Q1 2021 Sweepstakes
This could be your chance to win a free vacation at a luxury resort, a prize worth up to $2,043.
Entry Frequency: One time per person/email
End Date: March 31st, 2021
Eligibility: Open to the U.S. and Canada (void in PQ)
More Information about this Sweepstakes
Enter Sweepstakes Directly

5. 2021 Country Music Cruise Giveaway
Enter for your chance to win a week-long cruise for two people on board The 2021 Country Music Cruise.
Entry Frequency: 1 x daily per person
End Date: August 1st, 2021
Eligibility: Open to residents of the United States (void in Alaska, Hawaii, and Rhode Island)
More Information about this Sweepstakes
Enter Sweepstakes Directly

6. 2022 Soul Train Cruise Giveaway
Here’s your shot at a free seven-night cruise aboard The 2022 Soul Train Cruise valued at $4,450.
Entry Frequency: 1 x daily per person
End Date: October 29th, 2021
Eligibility: Open to residents of the United States (void in Alaska, Hawaii, and Rhode Island) who have a valid passport
More Information about this Sweepstakes
Enter Sweepstakes Directly

7. Expedia Cruises – Win a Dream Vacation 2021 Sweepstakes
Enter for your chance to win a seven-night Caribbean cruise for two people.
Entry Frequency: One time per person/email
End Date: November 5th, 2021
Eligibility: Open to residents of the United States, Canada, and Mexico
More Information about this Sweepstakes
Enter Sweepstakes Directly

8. Rock and Romance Cruise – 2022 Cabin Giveaway
Enter for your chance to win a seven-night Rock and Romance Cruise for two people.
Entry Frequency: 1 x daily per person
End Date: November 26th, 2021
Eligibility: Open to residents of the United States (void in Alaska, Hawaii, and Rhode Island)
More Information about this Sweepstakes
Enter Sweepstakes Directly

9. 2022 Ultimate Disco Cruise Giveaway
Enter for your chance to win a five-night The Ultimate Disco Cruise for two people.
Entry Frequency: 1 x daily per person
End Date: December 3rd, 2021
Eligibility: Open to residents of the United States (void in Alaska, Hawaii, and Rhode Island)
More Information about this Sweepstakes
Enter Sweepstakes Directly

An up-to-date listing of vacation sweepstakes offering free travel to Europe, the Caribbean, and other destinations outside of the United States. Win free trips to Rome, Paris, the UK, and other international destinations.