Win a Free Vacation Sweepstakes 2026
Vacation sweepstakes give participants the opportunity to win exciting travel prizes such as luxury resort stays, cruise vacations, and theme park trips. Many brands and travel companies run promotional giveaways where entrants can win trips to destinations like Hawaii, the Caribbean, Europe, or popular theme parks.On this page you can explore the latest vacation sweepstakes currently open for entry. These giveaways may include all-inclusive resort vacations, cruise trips, airline ticket sweepstakes, and travel prize contests. Most promotions are free to enter and are open to eligible residents of the United States.Check back often because new travel sweepstakes and trip giveaways are added regularly, giving you more chances to win unforgettable vacation experiences.
2026 El Estepario's Drum Set Giveaway – Win a Signed Pearl Drum Kit & Spain Trip Worth $9,578
Worldwide
Club Wyndham Wander Your Way Sweepstakes – Win a 7-Night Greece Vacation, Wyndham Rewards Points & Travel Credits [1507 Winners]
![Club Wyndham Wander Your Way Sweepstakes – Win a 7-Night Greece Vacation, Wyndham Rewards Points & Travel Credits [1507 Winners]](https://www.sweepstakesbible.com/img/sweepstakes/62/club-wyndham-wander-your-way-sweepstakes-greece-trip.jpg?t=1793338405)
United States
Union Plus Take Your PTO Promotion – Win $5,000 Cash and Dream Vacations [14 Winners]
![Union Plus Take Your PTO Promotion – Win $5,000 Cash and Dream Vacations [14 Winners]](https://www.sweepstakesbible.com/img/sweepstakes/62/union-plus-take-your-pto-travel-cash-sweepstakes.jpg?t=1793337895)
United States
Travel + Leisure World's Best Awards 2027 Giveaway – Win a $35,772 Viking River Cruise for Two
United States
iHeartRadio A Perfect Circle Flyaway Sweepstakes – Win a $3,500 Hawaii Concert Trip
United States
PEOPLE App InStyle Roadway Party Sweepstakes – Win a $3,500 Las Vegas Party Prize
United States
SiriusXM John Mayer at Sphere Las Vegas Sweepstakes: Win a $3,000 VIP Concert Trip for Two
United States
T-Mobile Tuesdays Week Sweepstakes: Win 1 Million Southwest Rapid Rewards Points and $5,142 Cash
United States
The Kewpie Japan Experience Sweepstakes: Win a $15,000 Trip to Japan for Two
United States
Tortuga 2027 Flyaway Contest: Win a $4,700 Tortuga Music Festival Trip for 2
United States
Vacation Sweepstakes – Win Free Trips & Travel Giveaways
Vacation sweepstakes give participants the opportunity to win exciting travel prizes such as luxury resort stays, cruise vacations, and theme park trips. Many brands and travel companies run promotional giveaways where entrants can win trips to destinations like Hawaii, the Caribbean, Europe, and popular theme parks.
On this page you can find the latest vacation sweepstakes and travel giveaways currently open for entry. These promotions may include all-inclusive resort vacations, airline ticket sweepstakes, cruise prizes, and family trips to popular destinations. Some giveaways offer daily entry opportunities while others allow a single entry during the promotion period.
Many travel sweepstakes include prize packages that cover round-trip airfare, hotel accommodations, resort stays, meals, and additional travel experiences. Sponsors often include well-known brands, travel companies, and promotional partners offering these giveaways as part of marketing campaigns.
New trip sweepstakes and vacation giveaways are added regularly, so check this page often to discover the latest opportunities. Whether you are hoping to win a tropical getaway, a cruise vacation, or a theme park trip, these sweepstakes provide a chance to win memorable travel experiences.