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 snowboard prize package with the Cutty Sark Gear All Year Sweepstakes.
Contest ends: December 31, 2025
Entry limit: Monthly Entry
Status: Open
Eligible for USA ResidentsWin a snowboard prize package with the Cutty Sark Gear All Year Sweepstakes.
Contest ends: December 31, 2025
Entry limit: Monthly Entry
Status: Open
Eligible for USA ResidentsEnter the Cutty Sark Gear All Year Sweepstakes to win a snowboard and other exciting prizes.
Contest ends: December 31, 2025
Entry limit: Monthly Entry
Status: Open
Eligible for USA ResidentsWin a snowboard prize package with the Cutty Sark Gear All Year Sweepstakes.
Contest ends: December 31, 2025
Entry limit: Monthly Entry
Status: Open
Eligible for USA ResidentsWin a snowboard prize in the Cutty Sark Gear All Year Sweepstakes, with monthly prizes including a $300 AirBnB gift card and more.
Contest ends: December 31, 2025
Entry limit: Monthly Entry
Status: Open
Eligible for USA ResidentsWin a snowboard prize package with the Cutty Sark Gear All Year Sweepstakes.
Contest ends: December 31, 2025
Entry limit: Monthly Entry
Status: Open
Eligible for USA ResidentsWin a snowboard prize in the Cutty Sark Gear All Year Sweepstakes, valued at $1,240, with monthly prizes including an Airbnb gift card.
Contest ends: December 31, 2025
Entry limit: Monthly Entry
Status: Open
Eligible for USA ResidentsWin $1,240 in gear and prizes, including a $300 Airbnb gift card, snowboard, paddleboard, and more.
Contest ends: December 31, 2025
Entry limit: Monthly Entry
Status: Open
Eligible for USA ResidentsWin concert show tickets in the ongoing sweepstakes at Party Guru, with new giveaways added frequently.
Contest ends: December 31, 2025
Entry limit: Single Entry
Status: Open
Eligible for USA ResidentsWin a snowboard prize package with the Cutty Sark Gear All Year Sweepstakes.
Contest ends: December 31, 2025
Entry limit: Monthly Entry
Status: Open
Eligible for USA ResidentsWin a snowboard prize package valued at $1,240 with Cutty Sark's Gear All Year Sweepstakes.
Contest ends: December 31, 2025
Entry limit: Monthly Entry
Status: Open
Eligible for USA ResidentsWin a 2-night trip for your nominated minor hockey team to the 2025 Memorial Cup in Rimouski, Quebec, and get to practice with Hockey Hall of Fame Legend Jarome Iginla.
Contest ends: February 28, 2025
Entry limit: Single Entry
Status: Open
Entry method: Web Submission
Eligible for Canadian Residents