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 7-night trip for two to the Cayman Islands and golf, valued at $14,600.
Contest ends: November 30, 2025
Entry limit: Single Entry
Status: Open
Eligible for Canadian ResidentsWin one of eight prizes worth $60,000, including trips to Paris and Greece, by picking up a Trevi sign and uploading a picture.
Win a 4-night trip to San Antonio, Texas with flights & accommodations valued at $5,000
Win a $15,000 Formula 1 US trip package with Heineken's sweepstakes, featuring tickets to Miami, Austin, and Las Vegas races.
Contest ends: November 30, 2025
Entry limit: Daily Entry
Status: Open
Eligible for USA ResidentsYou could win one of six prizes of $3,000 in Ticketmaster e-gift cards.
Contest ends: December 1, 2025
Entry limit: Single Entry
Status: Open
Eligible for USA ResidentsWin a $8,500 Las Vegas Formula One trip package including tickets to the race and $2,500 in cash to help cover taxes.
Contest ends: December 7, 2025
Entry limit: Daily Entry
Status: Open
Eligible for USA ResidentsWin hotel stays and winter festival experiences in Vancouver with the Very Merry Vancouver Giveaway.
Contest ends: December 12, 2025
Entry limit: Daily Entry
Status: Open
Eligible for Canadian ResidentsEligible for USA ResidentsWin a $10,000 travel voucher or one of 11 $300 vouchers in our 30th birthday sweepstakes with Flight Centre.
Contest ends: December 19, 2025
Entry limit: Single Entry
Status: Open
Eligible for Canadian ResidentsFrontera Wines is giving away a $4,000 trip for two to attend the 2026 Grammy Awards. Enter now and make unforgettable memories with your loved one.
Contest ends: December 31, 2025
Entry limit: Daily Entry
Status: Open
Eligible for USA ResidentsWin a UFC event trip and 19 Crimes/UFC merchandise in this exciting contest.
Contest ends: December 31, 2025
Entry limit: Daily Entry
Status: Open
Eligible for USA ResidentsWin a 2-night trip for two to Las Vegas to attend a UFC Fight event, plus an ESPN+ Pay-Per-View access code and a backpack.
Contest ends: December 31, 2025
Entry limit: Weekly Entry
Status: Open
Eligible for USA ResidentsWin two 3-Day Rhinestone Saloon passes to the 2026 Stagecoach Festival in Indio, California, valued at $2,800.
Contest ends: December 31, 2025
Entry limit: Daily Entry
Status: Open
Eligible for USA Residents