Vacation Contests
This list contains many contests for Trip that are open world wide. If you are looking for local contests checkout the contest locale archive.
Win a $4,000 Hawaii trip for two with 805 Beer's sweepstakes.
Contest ends: September 30, 2025
Entry limit: Single Entry
Status: Open
Eligible for USA ResidentsWin a 2-night stay in Oxford, MS, plus lunch and a welcome bag.
Contest ends: September 30, 2025
Entry limit: Single Entry
Status: Open
Eligible for USA ResidentsEnter to win a $6,992 cruise vacation or one of 330 instant win prizes of Celebrity merchandise in the Xcel Dream Makers Sweepstakes & Instant Win.
Contest ends: September 30, 2025
Entry limit: Daily Entry
Status: Open
Eligible for Canadian ResidentsEligible for USA ResidentsWin $3,000 in Live Nation gift cards or a $300 prize with the Mi Campo Tequila Concerts For A Year Sweepstakes.
Contest ends: September 30, 2025
Entry limit: Daily Entry
Status: Open
Eligible for USA ResidentsWin a trip for two to the 2025 MLB All-Star Game in Atlanta, Georgia, with tickets and accommodations included.
Contest ends: October 1, 2025
Entry limit: Daily Entry
Status: Open
Eligible for USA ResidentsWin a luxurious Veranda stateroom cruise and $1,000 credit on Christian McBride's World at Sea voyage in January 2026.
Contest ends: October 1, 2025
Entry limit: Single Entry
Status: Open
Eligible for USA ResidentsWin $5,000 airfare to Europe or tickets to a Toronto FC game with the Tunnel Club Takeoff Contest.
Contest ends: October 10, 2025
Entry limit: Single Entry
Status: Open
Eligible for Canadian ResidentsWin a $4,950 trip for two to Las Vegas with a 2-day tuition at the Cadillac V-Performance Academy Driving School.
Contest ends: October 11, 2025
Entry limit: Single Entry
Status: Open
Eligible for USA ResidentsWin a $10,980 Central Asia trip or a 3-night Banff ski getaway valued at $2,500
You could win one of two prizes of a 2-night trip for two to NBA or WNBA finals and a gift box, valued at $4,750. There are also 25 prizes of signed sports memorabilia.
Contest ends: October 20, 2025
Entry limit: Single Entry
Status: Open
Eligible for USA ResidentsYou could win a $10,000 vacation in Prince Edward Island including golf, accommodations, a car rental and more.
Contest ends: October 31, 2025
Entry limit: Single Entry
Status: Open
Eligible for Canadian ResidentsYou could win 1,000,000 Wyndham Rewards Points, a 7-night stay for four at your choice of Club Wyndham location and a $2,500 airfare credit, valued at $19,593. There are also monthly prizes of 120,000 Wyndham Rewards Points or weekly prizes of 30,000 points.
Contest ends: October 31, 2025
Entry limit: Daily Entry
Status: Open
Eligible for USA Residents