Friday newsletters always feature luxury travel contests, tips, or news.
Today (May 7, 2021): Travel contests & sweepstakes: win luxury holidays!
Every month, you can win exclusive holidays in my pick of the best luxury travel contests & sweepstakes on the internet. These contests are weekly updated on my travel blog here, so check back regularly.
In this issue: win two luxury holidays the Maldives, a vacation with George Clooney in Italy, as well as holidays to Malaysia, Portugal, Italy, South Africa, Bali, Antigua, Scotland and Cyprus.

- Win a three night stay at any Small Luxury Hotels of the World (SLH). The grand prize is a three night stay at any SLH hotel around the world, based on two people sharing arriving between 1st June 2021 to 30th June 2022. SLH’s portfolio includes 520 hotels in more than 90 countries.
- Eligibility: open to all
- End date: May 23, 2021
- Enter the travel contest: click here
- Win a three night stay in the Maldives. The grand prize is a three-night stay in a overwater pool villa at Mövenpick Resort Kuredhivaru Maldives. This prize includes breakfast at ONU Marché, complimentary Movenpick chocolate hour each day, free non-motorized watersports (kayaks, stand-up-paddleboarding, windsurfing), plus free snorkelling gear throughout your stay. Note: travel is not included in the prize.
- Eligibility: open to all
- End date: May 31, 2021
- Enter the travel contest: click here
- Win a five night luxury holiday in the Maldives. The grand prize is a 5 night bed and breakfast stay for two adults in a beach bungalow with pool at the luxurious Huvafen Fushi resort in the Maldives. Note: roundtrip airport transfers by speedboat are included in the prize but international flights are not.
- Eligibility: open to all
- End date: May 31, 2021
- Enter the travel contest: click here
- Win a vacation with George Clooney & Amal in Lake Como, Italy. The grand prize is includes a meal made of all their favorite local foods, as well as a “cheers to life” and the chance to snap a photo to remember it all by. Flights and hotel are included in the prize.
- Eligibility: open to most countries
- End date: May 16, 2021
- Enter the travel contest: click here
- Win a one night stay in Kuala Lumpur, Malaysia. The grand prize consists of a one-night stay inclusive of breakfast for two guests at Banyan Tree Kuala Lumpur. The Banyan Tree Hotel Group is also giving away other hotel stays over the coming weeks via its Instagram page.
- Eligibility: open to all
- End date: May 11, 2021
- Enter the travel contest: click here
- Win a two night luxury break in Lisbon, Portugal. The grand prize is a two-night stay in at The Vintage Hotel & Spa in Lisbon. This prize includes breakfast served in your room each morning plus a three-course dinner for two in Blue Bar & Restaurant or the V Rooftop Bar on one evening of your stay.
- Eligibility: open to all
- End date: May 31, 2021
- Enter the travel contest: click here
- Win a two night luxury break in Tuscany, Italy. The grand prize is a two-night stay in a romantic room at Torre A Cona Wine Estate in Tuscany. This prize includes breakfast served in your room each morning plus a three-course Chef’s Suggestion dinner for two in Osteria Torre a Cona on one evening of your stay.
- Eligibility: open to all
- End date: May 31, 2021
- Enter the travel contest: click here
- Win a safari in South Africa. The grand prize is a seven-day stay for two at South Africa’s newest bush resort, Oase by 7 Star Lodges. Flights to and from Johannesburg’s Oliver Tambo International Airport, internal flights, game drives and meals included.
- Eligibility: open to all
- End date: May 24, 2021
- Enter the travel contest: click here
- Win a post-pandemic holiday in Bali, Indonesia. The grand prize is a five-night stay for two at Nirjhara Resort on a bed & breakfast basis, and includes flights plus £250 to spend on Hush’s summer collection to ensure you’re all kitted out for the trip.
- Eligibility: open to all
- End date: June 20, 2021
- Enter the travel contest: click here
- Win a four night stay in the Caribbean island of Antigua. The grand prize includes airfare for two and a four night stay at the Carlisle Bay Resort in an ocean suite, inclusive of breakfast and afternoon tea.
- Eligibility: open to USA residents
- End date: May 23, 2021
- Enter the travel contest: click here
- Win a five night stay in the Caribbean island of Antigua. The grand prize is five nights at Hammock Cove Antigua in a luxury villa, all meals including breakfast, lunch and dinner, small bites throughout the day, afternoon tea, premium beverages, wine and champagne, and a variety of land and water activities.
- Eligibility: open to residents of the USA, UK, Canada, and the Caribbean
- End date: May 17, 2021
- Enter the travel contest: click here
- Win a five night luxury stay in Crete, Greece. The grand prize is a five night stay at the 5-star Daios Cove Luxury Resort & Villas staying in an all-inclusive deluxe junior suite plus return flights for up to 3 people. Note: travel needs to take place within 14 September to 31 October 2021, 01 April to 30 June 2022 and 14 September to 31 October 2022, subject to availability.
- Eligibility: open to UK residents
- End date: June 13, 2021
- Enter the travel contest: click here
- Win a family trip to Orlando in Florida, USA. To celebrate the launch of their new direct route from Manchester to Orlando, Aer Lingus is giving you the chance to enjoy a family holiday of a lifetime. The grand prize includes return flights for 4 from Manchester to Orlando, fully inclusive car hire for the duration of your stay, five nights accommodation in a 4-star hotel in Orlando, plus travel insurance.
- Eligibility: open to UK residents
- End date: May 9, 2021
- Enter the travel contest: click here
- Win a two night stay in Edinburgh, Scotland. The grand prize is a two-night stay for a winner and one guest at Kimpton Charlotte Square Hotel in Edinburgh, including dinner each evening and a spa treatment for two.
- Eligibility: open to UK residents
- End date: May 22, 2021
- Enter the travel contest: click here
- Win a two night stay in Glasgow, Scotland. The grand prize is a two-night stay for a winner and one guest at Kimpton Blythswood Square in Glasgow, including dinner each evening and a spa treatment for two.
- Eligibility: open to UK residents
- End date: May 22, 2021
- Enter the travel contest: click here
- Win a 10-night island-hopping tour in Scotland. The winner and a guest will set off on a 10-night, self-drive odyssey courtesy of National Geographic Traveller and McKinlay Kidd. The prize includes two nights on the Isle of Barra, two on the Uists, two on Harris, two on Lewis and two on Skye in hand-picked accommodation. The prize also includes ferry travel with CalMac for a car and two passengers.
- Eligibility: open to UK residents
- End date: May 13, 2021
- Enter the travel contest: click here
- Win a 14-night European cruise for two. The grand prize is a 14-night Princess Cruise for two, with stop-offs along the coast of France, Portugal and Spain, and with food, entertainment and 24-hour room service included.
- Eligibility: open to UK residents
- End date: May 13, 2021
- Enter the travel contest: click here
- Win a 2-night active holiday in Portugal. The grand prize is a two-night active holiday for two at Portugal’s Quinta do Lago, including breakfast, supper, a day’s membership at the health club, The Campus, and a round of golf on one of its world-class courses
- Eligibility: open to UK residents
- End date: May 27, 2021
- Enter the travel contest: click here
- Win a holiday in Cyprus. The grand prize is a three-night holiday for two at Parklane, a Luxury Collection Resort and Spa, in Limassol in Cyprus. Breakfast, supper, a spa treatment and return flights from London are included in the price.
- Eligibility: open to UK residents
- End date: May 6, 2021
- Enter the travel contest: click here
- Win a safari holiday to Kruger National Park, South Africa. The grand prize includes round trip flights, transfers and a seven night safari to Hippo Hollow Resort in Kruger National Park.
- Eligibility: open to UK residents
- End date: June 30, 2021
- Enter the travel contest: click here
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Hi, the contest to “Win a five night stay in the Caribbean island of Antigua. The grand prize is five nights at Hammock Cove Antigua in a luxury villa, all meals including breakfast, lunch and dinner, small bites throughout the day, afternoon tea, premium beverages, wine and champagne, and a variety of land and water activities.
Eligibility: open to residents of the USA, UK, Canada, and the Caribbean”
Via a Brides magazine is only open to U.S residents according to the rules.