Latest Travel Contests and Sweepstakes

October 28, 2026

Win a 4-Day Walt Disney World Family Vacation in the Visit Orlando Sweepstakes

Disney families, this is one of the better Orlando prizes we’ve seen lately. The Win an Orlando Family Vacation Sweepstakes is sending one winner and up to three guests to Walt Disney World with three nights at a Moderate Disney Resort, up to four 4-Day Park Hopper tickets, and up to $1,000 in Frontier Airlines flight vouchers. You can enter once per day, which is worth remembering on a prize like this. The flight vouchers are capped at $250 per traveler, so if your airfare costs more you’ll need to cover the difference yourself. Open to residents of the contiguous U.S. and D.C. age 21+. Ends January 18, 2027.

October 23, 2026

Win a 4-Night Miami or San Diego Getaway in the Ultimate RHA Getaway Sweepstakes

Choose Miami or San Diego for this one. The Ultimate RHA Getaway Sweepstakes is picking four grand prize winners, and each gets a 5-day/4-night trip for two with round-trip airfare, hotel accommodations at either Fontainebleau Miami Beach or the Catamaran Resort Hotel and Spa in San Diego, airport transportation, an excursion, and a $1,000 check for meals and other incidentals. The prize also includes an optional RHA facial filler treatment with an expert injector, subject to medical eligibility, and you can decline the treatment without losing the rest of the trip. It’s a one-time online entry. Open to U.S. residents 22+. Ends December 31, 2026.

October 21, 2026

Win a VIP Breeders’ Cup Trip + $5,000 Cash + $5,000 Betting Credit

Horse racing fans, this is a big one. The 2026 Breeders’ Cup The Champion’s Ticket is sending one winner and a guest to the 2027 Breeders’ Cup World Championships at Belmont Park in New York, with round-trip airfare, four nights of hotel accommodations, airport and racetrack transportation, and two VIP tickets, plus $5,000 cash and $5,000 in betting credit for the races. The trip is tied to the October 29–30, 2027 Breeders’ Cup, and if selected you’ll need to be reachable within 24 hours of the initial winner notification. Open to residents of the U.S. and Canada excluding Quebec who are 21+. Ends November 30, 2026.

October 20, 2026

Win an 8-Day Viking European River Cruise for Two with Airfare

This is exactly what I like to see in a travel prize: the flights are included. The 2026 MASTERPIECE European River Cruise Sweepstakes is sending one winner and a guest on an 8-day Viking river cruise in Europe, with a choice of six itineraries including the Danube, Rhine, Bordeaux, Normandy and Provence, plus a veranda stateroom, onboard meals, an included excursion at every port, round-trip economy airfare and airport-to-ship transfers. You can enter once per day and earn up to five additional entries by referring friends. You’ll need a valid U.S. or Canadian passport when you enter, and the cruise must take place during 2027. Open to residents of the U.S. and Canada excluding Quebec, age 21+. Ends November 24, 2026.

October 16, 2026

Win a 6-Night Trip to Japan for Two in the House of Suntory Japan Travel Package Promotion

Japan is calling. The House of Suntory Japan Travel Package Promotion is sending one winner and a guest to Japan with round-trip economy airfare, four nights in Tokyo, two nights in Kyoto, and first-class train travel between Tokyo and Kyoto, plus a planned itinerary that may include dining and cocktail experiences, a Yamazaki Distillery visit, and a day trip to Osaka. You get one standard entry, one optional bonus entry for signing up for House of Suntory marketing, and 10 more optional entries by completing the Art of Suntory Time experience and submitting the generated image, with no social media post required. Mobile SMS verification is required to enter. Travel must be completed during 2027, and no alcohol is included in the prize. Open to residents of the U.S., Canada excluding Quebec, and the UK who are 21+ and of legal drinking age. Ends December 1, 2026.

October 15, 2026

Win a 5-Night Ski + Heli-Ski Trip to Golden, BC in the Win a Ski Trip to Golden Sweepstakes

Skiers and snowboarders, this is a big one. The Win a Ski Trip to Golden sweepstakes is sending one winner and a guest to Golden, British Columbia for five nights, including up to CAD $2,000 toward round-trip airfare, airport and local transportation, two days of skiing or snowboarding at Kicking Horse Mountain Resort, one day of CMH heli-skiing, lunch at Eagle’s Eye Restaurant, up to CAD $700 for dining, and up to CAD $300 for shopping in Golden. The trip must take place during January through March 2027, with some blackout dates, and the heli-skiing portion requires both travelers to be strong intermediate-to-advanced skiers or snowboarders comfortable on black-diamond terrain. You get one entry from the form, with two optional bonus entries for agreeing to partner marketing emails, and you can unsubscribe later without losing the bonus entries. Open to residents of Canada (excluding Quebec), the U.S. (excluding New York, Washington, and Florida), and the UK who are 19+. Ends November 30, 2026.

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