Vacation Sweepstakes and Giveaways 2026 - Page 6
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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
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
Enter the USA Pickleball Association 2026 Golden Ticket Sweepstakes for a chance to win an incredible prize. One lucky winner will receive a four-day, three-night all-inclusive Caribbean vacation for two adults in a deluxe luxury room at any Sandals Resort, valued at $3,186.00. Don't miss this opportunity to win a dream getaway - enter to win the USA Pickleball Association 2026 Golden Ticket Sweepstakes today.
Win $3,186 in value – USA Pickleball Association 2026 Golden Ticket Sweepstakes - Enter Now
Enter to win the AM 570 - The Answer Dream Vacation for Two to Italy Sweepstakes and take home an unforgettable Italy Unfiltered trip for two. One lucky Grand Prize winner will receive a 10-day getaway from September 29 to October 8, 2026, complete with 4-star accommodations, guided tours, and more. The prize package, valued at $9,990, includes centrally located hotels, entrance fees, daily breakfast, and four dinners with drinks. However, winners are responsible for their own air travel to and from Rome, Italy. Don't miss your chance to win this incredible prize - enter the AM 570 - The Answer Dream Vacation for Two to Italy Sweepstakes before 12:59 am EDT on September 1, 2026.
Win $9,990 in value – AM 570 - The Answer Dream Vacation for Two to Italy Sweepstakes - Enter Now
Get ready to win big with E. & J. Gallo Winery's Barefoot’s Here Comes The Fun Sweepstakes. Enter for a chance to win a $5,000 Visa Gift Card, perfect for a dream vacation. The sweepstakes starts on March 1, 2026, and ends on June 30, 2026. To enter, simply scan the QR code on participating Barefoot Wine point of sale materials or visit https://www.barefootwine.com/dream-vacation-sweeps.html. Open to legal US residents (excluding Utah) 21+, one entry per person/email address. Winner will be selected by random drawing on July 1, 2026. Don't miss out on this amazing opportunity to win with Barefoot Wine's Here Comes The Fun Sweepstakes, sponsored by E. & J. Gallo Winery.
Win $5,000 in value – Barefoot’s Here Comes The Fun Sweepstakes - Enter Now
Enter to win the One Country The Skyview Treehouse Sweepstakes for a chance to escape to a secluded 18-person treehouse in the Great Smoky Mountains. This mountainside retreat offers modern comforts and natural elements, perfect for a unique 7-day vacation getaway for multiple families. Enjoy sliding bi-fold doors, multiple bunk rooms, a kitchenside patio, and a 7-Person Dynasty Spa hot tub and hot-rock cedar sauna. The prize package includes flights for four to Sevierville, TN, with a stay from September 20 - 27, 2026. Don't miss this free entry sweepstakes to win an unforgettable prize.
Win $10,000 in value – One Country The Skyview Treehouse Sweepstakes - Enter Now
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
Enter the Voodoo Ranger Mystery Vacation Giveaway for a chance to win a $10,000 gift card to plan an unforgettable "mystery" vacation. The Grand Prize includes round-trip flights, accommodations, local experiences tailored to your taste, and travel between destinations. Choose from a hotel or Airbnb-style place, with the option to upgrade to 4+ star accommodations. The travel service currently offers trips from select US airports, including ATL, BOS, ORD, DFW, DEN, DTW, IAH, LAX, MIA, MSP, JFK, SFO, SEA, and IAD. With an Approximate Retail Value of $10,000, this sweepstakes is a must-enter. The giveaway ends at 11:59:59 pm MT on 8/31/26, so enter to win your dream vacation today with the Voodoo Ranger Mystery Vacation Giveaway.
Win $10,000 in value – Voodoo Ranger Mystery Vacation Giveaway - Enter Now
Enter the Werther’s Original Spring Sweepstakes for a chance to win a grand prize 3-night vacation to Walt Disney World Resort near Orlando, Florida, for you and up to five guests, courtesy of Storck, the company behind Werther’s Original. To enter, simply purchase any two Werther’s Original products and submit an online form, or send a mail-in entry without making a purchase. The grand prize winner will receive a fantastic vacation package with a total value of $10,000.00, including round-trip airfares, ground transportation, hotel accommodations, and theme park tickets. Don't miss your chance to win with Werther’s Original - enter by June 30, 2026, at 11:59 PM ET, or mail in your entry postmarked by June 30, 2026, and received by July 7, 2026. The vacation must be taken between August 16, 2026, and December 31, 2027. With Werther’s Original, you can enter to win a prize that's an unforgettable experience, brought to you by Storck.
Win $10,000 in value – Werther’s Original Spring Sweepstakes - Enter Now
Enter the Topps The Magical Grand Prize Sweepstakes for a chance to win an unforgettable prize package valued at approximately $9,410.00, courtesy of Disney. This amazing giveaway includes a 3-night, 4-day vacation to the Disneyland Resort, complete with roundtrip airfares, ground transfers, and a Concierge level room for you and up to 3 guests. You'll also receive 4-Day Disneyland Resort Park Hopper Tickets, an $800 Disney Gift Card, and reserved viewing for a World of Color show. To enter, look for a scratch-off redemption card in 2025 Topps Disneyland 70th Anniversary packs, or send a self-addressed stamped envelope to the specified address in the rules by March 27, 2026. The sweepstakes starts on February 26, 2026, and ends on June 30, 2026. Don't miss this opportunity to win big with Topps and Disney - enter the Topps The Magical Grand Prize Sweepstakes today for a free entry and a chance to make your dreams come true, courtesy of Topps.
Win $9,410 in value – Topps The Magical Grand Prize Sweepstakes - Enter Now
