Latest Travel Contests and Sweepstakes

June 15, 2026

Win a $5,000 Travel Gift Card in the Dramamine Your Why. Your Way. Sweepstakes

If a flexible travel prize sounds good, Dramamine Your Why. Your Way. Sweepstakes is giving one grand prize winner a $5,000 travel gift card from a sponsor-designated list of hotel or airline gift card providers. Additional prizes include Bose QuietComfort headphones and Dramamine product prize packs. You can enter once per day, with optional bonus entries available by spinning the vacation wheel after entering. Open to legal U.S. residents 18+. Ends September 7, 2026.

June 12, 2026

Win a New York City Holiday Trip in the Snapple Americana QR Code Sweepstakes

If a holiday trip to New York City sounds exciting, Snapple Americana QR Code Sweepstakes is giving one winner a trip for two to NYC during the 2026 holiday season. The prize includes a 3-night stay, two tickets to an event at Madison Square Garden, and either a guided MET Museum tour or a private holiday history tour depending on travel dates. You can enter once per day during the promotion. Open to legal residents of the contiguous U.S. and D.C. who are 21+. Ends August 11, 2026.

May 29, 2026

Win a NASCAR Championship Weekend Trip in the CRAFTSMAN Race With CRAFTSMAN Sweepstakes

If NASCAR and tools are your kind of combo, CRAFTSMAN Race With CRAFTSMAN Sweepstakes is giving one Entry Period 1 winner a 5-day, 4-night trip for two to the 2026 NASCAR Cup Series Championship Weekend at Homestead-Miami Speedway, plus up to $700 in CRAFTSMAN tools. Two additional entry periods will award CRAFTSMAN tool prizes valued at up to $1,468.92 and $794. You can enter once per day during each applicable entry period. Open to legal U.S. residents 18+ who have reached the age of majority in their state. Ends November 8, 2026.

May 14, 2026

Win a Hawaii Wellness Retreat in the Waiākea Sweepstakes

If a relaxing island getaway sounds like the perfect prize, Waiākea Wellness Retreat Sweepstakes is giving away two Hawaii travel packages. One mainland U.S. winner will receive a 4-day, 3-night trip for two to the OUTRIGGER Kona Resort & Spa, including airfare, ground transportation, an activities credit, a private helicopter tour, and spa and dining credit. A separate Hawaii winner will receive an inter-island wellness trip with similar resort perks and a helicopter tour. It’s a simple one-time online entry, making this a great travel giveaway to add if ocean views, resort time, and unforgettable experiences sound good to you. Open to legal U.S. residents who have reached the age of majority in their state. Ends August 31, 2026.

May 13, 2026

Win a Family Trip to Barcelona in the Fresh Del Monte Toy Story 5 Sweepstakes

If a big family adventure sounds like your kind of prize, Fresh Del Monte Sweepstakes Celebrating the Release of Toy Story 5 is sending one winner, another adult, and two children to Barcelona, Spain. The trip package includes roundtrip airfare, five nights of hotel accommodations, daily breakfast, airport transfers, and a fun lineup of family-friendly experiences like a GPS-led mini car tour, museum visits, a horseback excursion in Montserrat, park admission, a science museum visit, and even space-themed gelato. It’s a simple one-time online entry, with optional trivia just for fun. Open to legal residents of the U.S., D.C., and Canada who are 18+ or the age of majority. Ends July 31, 2026.

May 7, 2026

Win a Pokémon Family Adventure in the Campbell’s Pokémon Promotion

If your family loves Pokémon, Campbell’s Pokémon Promotion is serving up a fun mix of big prizes and instant wins. Three grand prize winners will each receive a Pokémon Family Adventure with funds for a trip to Chicago’s Field Museum to visit the Pokémon Fossil Museum, plus spending money, Chicago CityPASS, Pokémon plush dolls, backpacks, and Goldfish snacks. There are also 3,150 instant win prizes, including Pokémon backpacks, Pokémon Center gift cards, and free Goldfish coupons, so this one has lots of chances to win. Entries are accepted daily, and you can play the instant win game each time you enter. Open to legal U.S. residents 18+. Ends September 13, 2026.

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