Explore Travel Sweepstakes to win flights, hotel stays, dream getaways and more. Enter today for a chance to travel the world. In 2026, Classic Vacations is celebrating three milestone anniversaries with a year-long sweepstakes program highlighting Europe, The Islands of Tahiti, and Costa Rica.
Throughout the year, travel advisors can earn chances to win by booking eligible travel and participating in destination quiz drawings. Check back monthly for updated fun facts, prize details, and quiz announcements. Win your dream vacation for free! Travel accross America, Europe, Asia and beyond in these fabulous vacation sweepstakes!
Enter the best Vacation Sweepstakes 2026 to win free trips! Explore dream destinations with legit vacation giveaways, travel contests, and more. Win a FIFA World Cup 2026 Group Stage Trip with Casamigos Enter the Casamigos FIFA World Cup 2026™ Group Stage Sweepstakes for a chance to experience one of the biggest sporting events on the planet, live and in person. Four winners will each score a World Cup group stage trip package that includes two match tickets, round-trip airfare, hotel accommodations, a merchandise gift basket, and a.
The sweepstakes is open to Marriott Bonvoy members, with entries accepted from December 22 to January 1, 2026. With the flexibility to choose from Marriott Bonvoy's vast global portfolio of properties, the grand prize offers winners the chance to design their dream vacation, whether that means a bucket. Enter by March 31, 2026 Win a $1,500 Saks Fifth Avenue gift card (enter monthly!) There is one (1) Grand Prize available.
The Grand Prize consists of a $1,500 Saks Gift Card Sweepstakes is open to legal residents of the 50 United States and the District of Columbia, age 18 and older Enter by January 31, 2026 Win an RV. OFFICIAL SWEEPSTAKES RULES REQUEST: For a copy of these Official Rules, send a request specifying Official Rules along with a self-addressed, stamped envelope postmarked by January 31, 2026 and received by February 5, 2026, and mail to: Compliance/"Travel Marketplace Vacation Giveaway" Sweepstakes Official Rules, Box 469, Stonington, CT 06378. Friday newsletters always feature luxury travel contests, tips, or news.
Today: 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. Travel Sweepstakes We have the best list of travel sweepstakes you can enter to win a vacation, including the ones from Travel Channel.
Some might be ending soon so hurry up and you could be among the winners! Expedia Cruises Sweepstakes 2026 Enter the Expedia Cruises Sweepstakes today for a chance to win a $5,000 cruise for two to the Caribbean, airfare included. Sunday, January 25, 2026 5:38.
