Vacation Contests
This list contains many contests for Vacation Contests that are open world wide. If you are looking for local contests checkout the contest locale archive.
Enter now for your chance to win a trip for two to Teddy Swims' concert in the Hamptons, courtesy of White Claw Hard Seltzer.
Contest ends: September 14, 2026
Entry limit: Daily Entry
Status: Open
Eligible for USA ResidentsWin a trip for two to a Teddy Swims concert with White Claw Hard Seltzer sweepstakes.
Contest ends: September 14, 2026
Entry limit: Daily Entry
Status: Open
Eligible for USA ResidentsParticipate in the International Traveller 2026 Readers’ Choice Awards to win luxurious travel experiences worth over $120,000. Vote now for your favorite destinations and operators.
Enter the Cayman Jack sweepstakes for a chance to win a $25,000 vacation prize and fund a dream trip to a tropical paradise.
Contest ends: September 14, 2026
Entry limit: Daily Entry
Status: Open
Eligible for USA ResidentsUpload a photo of your CFL team spirit for a chance to win $500,000 prize and a trip to the Grey Cup.
Contest ends: September 14, 2026
Entry limit: Single Entry
Status: Open
Eligible for Canada ResidentsEnter for a chance to win one of three luxury trip to Montreal packages, including an exclusive meet and greet with a champion.
Contest ends: September 14, 2026
Entry limit: Daily Entry
Status: Open
Eligible for Canada ResidentsEnter now for a chance to win an Iconic Golf Trip to Scotland or one of 27,000 instant win golf gift cards.
Win a 3-night trip to San Diego for USA Pickleball National Championships with the Oceanview Sweepstakes!
Contest ends: September 15, 2026
Entry limit: Single Entry
Status: Open
Eligible for USA ResidentsEnter the Swing Big Contest for a chance to win a World Series trip for four, featuring a luxury prize package worth $20,000.
Contest ends: September 15, 2026
Entry limit: Weekly Entry
Status: Open
Eligible for Canada ResidentsEnter for a chance to win an athletic club trip for two to a premier golf or tennis tournament in Miami or Dallas.
Contest ends: September 15, 2026
Entry limit: Single Entry
Status: Open
Eligible for USA ResidentsEnter now for a chance to win a luxurious Sturbridge Massachusetts stay featuring dinner and activities valued at over five hundred dollars.
Contest ends: September 15, 2026
Entry limit: Single Entry
Status: Open
Eligible for USA ResidentsPurchase select wines for a chance to win a trip to Japan or instant $50 prepaid Mastercards in this winter promotion.