8 Epic Travel Contests And Sweepstakes Worth Entering This Winter

These travel offers are free and give you the chance to win gift cards, vacations and even a free dream wedding.

Published on Feb. 16, 2026

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Test your luck this winter with these exciting, travel-focused sweepstakes, giveaways and contests that could have you taking a free vacation in no time. From trips to national parks and New York City gift cards to a completely free, high-end wedding in Palm Beach, it's worth entering all of them to see what you can win.

Why it matters

These contests offer a unique opportunity for travelers to win free trips, experiences, and even a dream wedding, providing a chance to explore new destinations and create unforgettable memories without the financial burden.

The details

The contests include a Super Bowl ad giveaway from Volkswagen, a spring break getaway at the Cadillac Hotel & Beach Club in Miami Beach, a volunteer and vacation trip to Chilean Patagonia, an 88-night global stay giveaway from Shangri-La Hotels, a field trip to U.S. landmarks for lucky grade school students, free hotel stays and gift cards in New York City, a 'love lottery' from Walker Hotels, and a dream wedding prize at The Singer Oceanfront Resort in Palm Beach.

  • The Super Bowl ad giveaway deadline is March 2.
  • The Cadillac Hotel & Beach Club giveaway deadline is March 8.
  • The Chilean Patagonia volunteer and vacation trip takes place between March 22–26 or March 28–April 1.
  • The Shangri-La Hotels giveaway runs through February 21.
  • The U.S. landmarks field trip essay/art contest deadline is March 30.

The players

Volkswagen

An automotive manufacturer that is offering a trip to Taos, New Mexico, U.S. Men's National Team soccer tickets, and a new Golf GTI car as part of its Super Bowl ad giveaway.

Cadillac Hotel & Beach Club

A hotel in Miami Beach, Florida that is offering a two-night stay in an oceanfront suite, a $100 resort credit, and a pasta-making and charcuterie board experience as part of its spring break getaway giveaway.

Las Torres Patagonia

A family-owned reserve in Chilean Patagonia that is offering a five-night trip including round-trip airfare, hotel stay, and the opportunity to volunteer on trail restoration efforts as part of its '10 Volunteers for 10 Days' campaign.

Shangri-La Hotels

A hotel group that is giving away 88 complimentary nights across its properties around the world as part of its Chinese New Year celebration.

The Singer Oceanfront Resort

A Hilton Curio Collection hotel in Palm Beach, Florida that is offering a dream wedding package including waived venue fees, food and beverage credits, flowers and decor, and professional photography and videography.

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What’s next

The winners of the Super Bowl ad giveaway will be announced on March 2, and the Cadillac Hotel & Beach Club giveaway winner will be selected on March 8. The Chilean Patagonia volunteer and vacation trip will take place in late March or early April, while the Shangri-La Hotels giveaway and U.S. landmarks field trip essay/art contest will conclude by the end of February and March, respectively.

The takeaway

These travel contests and sweepstakes offer an exciting opportunity for adventurous and budget-conscious travelers to win free trips, experiences, and even a dream wedding, providing a chance to explore new destinations and create unforgettable memories without the financial burden.