Vacation Sweepstakes and Giveaways 2026 - Page 6

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Enter the Expedia Cruises Win a Dream Vacation 2026 Sweepstakes for a chance to win a 7-night Caribbean cruise for two, including roundtrip airfare, valued at up to $5,000. No purchase necessary. To enter, visit www.expediacruises.com and complete the entry form or enter in person at any Expedia Cruises location. Limit one entry per person, with additional entries available through referrals. Sweepstakes runs from January 1, 2026 to November 1, 2026. Winner will be selected in a random drawing on November 16, 2026. Expedia Cruises reserves the right to modify or cancel the sweepstakes. See official rules for details.

Win $5,000 in value – Expedia Cruises Win a Dream Vacation 2026 Sweepstakes - Enter Now

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Enter the M&M Heroic Cruise Adventure​ Contest for a chance to win an unforgettable prize. With 45 prizes up for grabs, you could be one of the lucky winners of a Secondary Prize or the Grand Prize. The Grand Prize is a 4- or 5-Night Disney Cruise Line vacation for you and up to three guests, valued at approximately CAD$20,000. This incredible Vacation Package includes round-trip airfares, a 1-night hotel stay, ground transportation, and a Disney Destiny cruise with meals and onboard gratuities. Alternatively, you could win one of 44 Secondary Prizes, including Disney+ Subscriptions or Cinema Gift Cards, with a total value of CAD$4,620. Don't miss your chance to win - enter the M&M Heroic Cruise Adventure​ Contest before the contest closes on August 31, 2026.

Win $24,620 in value – M&M Heroic Cruise Adventure Contest - Enter Now

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Get ready for adventure with the Eddie Bauer Adventure Club The Red Rocks and Roam Giveaway. Enter to win exciting prizes, including a Grand Prize package valued at up to $9,000, featuring a 7-night vacation for four at Club Wyndham Moab Resort in Moab, Utah, a $2,000 Airline Credit, and a $1,000 Virtual Promotional Prepaid Mastercard. Monthly and Weekly Prizes are also available, with twelve $750 Virtual Promotional Prepaid Mastercards and fifty-two $250 Virtual Promotional Prepaid Mastercards up for grabs. With a total ARV of $25,945, this free entry sweepstakes is a thrilling opportunity to win big. Prizes are non-transferable, and winners are responsible for all taxes. Join the Eddie Bauer Adventure Club and take a chance to win with this incredible giveaway from Eddie Bauer.

Win $25,945 in value – Eddie Bauer Adventure Club The Red Rocks and Roam Giveaway - Enter Now

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Enter the Choice Hotels Choice Privileges Sweepstakes for a chance to win exciting prizes. Choice Hotels International, Inc. is offering a grand prize deluxe vacation package to Hawaii, Las Vegas, or Orlando, including round-trip air transportation, 7-night accommodations, car rental, and 2,000,000 Choice Privileges Points, valued at $19,400. Alternatively, the grand prize winner can choose a $10,000 cash alternative. Additionally, 12 monthly prizes are available, each consisting of a 3-night stay at a Choice Hotels location, 100,000 Choice Privileges Points, a 5-day car rental, and a cruise, valued at $1,525. To enter, visit the website and follow the on-screen instructions, or use the alternate method of entry online without a mobile phone. Bonus entries are also available. The Choice Hotels sweepstakes is open to legal US residents 25 years or older, and winners must be Choice Privileges members. Enter now for a free chance to win, courtesy of Choice Hotels International, Inc. Giveaway begins on 5/1/26 at 12:00 AM ET and ends on 4/30/27 at 11:59 PM ET.

Win $37,700 in value – Choice Hotels Choice Privileges Sweepstakes - Enter Now

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Enter the Golf PEI Golf Vacation Giveaway Contest today for your chance to win an incredible PEI golf vacation valued at $10,000. This grand prize pack includes $7,500 in Golf PEI gift cards for golf rounds and accommodations, $1,000 in gift cards to Prince Edward Island restaurants, a $1,000 rental car voucher, $500 in Island activities, and 4 tickets to the 2027 Charlottetown Festival. Enter to win this amazing prize for free. Contest ends October 31, 2026.

Win $10,000 in value – Golf PEI Golf Vacation Giveaway Contest - Enter Now

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Enter the Classic Anniversary Sweepstakes, a year-long celebration by Classic Vacations, where travel advisors can win exciting prizes to Europe, The Islands of Tahiti, and Costa Rica. To participate, advisors must be 18+ years old, legal residents of the 50 US states or DC, and have an active account with Classic Vacations. Employees of Classic Vacations and their families are not eligible. The sweepstakes features three Destination Spotlights, each with a quiz, and advisors can earn entries through eligible bookings or by mailing a handwritten entry ( AMOE in rules ). The Europe Spotlight Period runs from January 6 to May 31, 2026, while the Tahiti & Costa Rica Spotlight Period is from June 1 to September 30, 2026. Nine prizes will be awarded, including trips to Rome, Florence, Venice, Mykonos, Santorini, and more. Travel must be completed by December 15, 2027, and is subject to availability and blackout dates. Enter now for a chance to win with Classic Vacations.

Win $270,000 in value – Classic Anniversary Sweepstakes - Enter Now

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Enter the Hilton Grand Vacations Jackpot Sweepstakes for a chance to win a luxurious vacation package to Hawaii, Las Vegas, or Orlando, valued at $18,600. The Grand Prize includes round-trip air, deluxe Hilton accommodations, $1,000 spending money, car rental, and 2,000,000 Hilton Honors Points, or choose $10,000. Plus, 12 Monthly Prizes are up for grabs, each featuring 3 nights at a participating Hilton hotel, 250,000 Hilton Honors points, and $500 spending money, valued at $1,825. Alternatively, monthly winners can opt for $1,000. To enter, visit https://www.hiltongrandvacations.com/lp/sweepstakes, spin the wheel for 50 entries, or use the Alternate Method of Entry. Complete the registration form, follow on-screen instructions, and earn bonus entries by opting-in to marketing messages. With no purchase necessary, enter now for a chance to win big with Hilton Grand Vacations. Monthly winners will be selected on or about the 7th of each month, and the Grand Prize winner on or about February 5, 2027.

Win $40,500 in value – Hilton Grand Vacations Jackpot Sweepstakes - Enter Now