Vacation Sweepstakes and Giveaways 2026
Vacation Giveaways
Found 37 total
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 Sonlight Vacations St. Patrick’s Giveaway to win a fantastic vacation voucher for a 7-night stay in one of the most popular locations. This exciting sweepstakes offers a chance to score a dream getaway, with the winner announced on March 18th, 2026. Take a chance and enter to win this incredible prize from Sonlight Vacations.
Win $700 in value – Sonlight Vacations St. Patrick’s Day Giveaway - 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 Katlyn with The Vacation Wizards Gift Card Giveaway for a chance to win a magical $50 Disney Gift Card! One lucky winner will be selected on March 7th, so act now and take a shot at this fantastic prize. It's a free entry to win, and you could be the one to receive this amazing gift card, courtesy of The Vacation Wizards. Don't miss out - enter to win today!
Win $50 in value – Katlyn with The Vacation Wizards Gift Card Giveaway - Enter Now
Enter the Cancun Winter Escape Sweepstakes for a chance to win a grand prize valued at $1500. One lucky winner will be chosen to receive a 3-night stay at the deluxe, all-inclusive Royalton Cancun Autograph Collection property. This amazing getaway is the perfect escape, and it's free to enter. Don't miss out on this incredible opportunity to win a dream vacation - enter the Cancun Winter Escape Sweepstakes today and take a chance at winning this fantastic prize. The Sweepstakes will end on 3/31/2026 at 11:59pm EDT.
Win $1,500 in value – Cancun Winter Escape 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
Enter the AppleVacations Ultimate Romantic Escape to Tulum Sweepstakes for a chance to win an unforgettable getaway valued at $3950. One lucky winner will receive a 3-night all-inclusive trip for two to Secrets Tulum Resort & Beach Club, including round-trip airfare and airport transfers. The grand prize package also features gift cards from top brands, including Korchmar, Aurate, Daniella Shevel, Sauipe Swim, RBA skincare, and a Visa Gift Card. To be eligible, travel must be completed by March 20, 2027. Submit your free entry by March 23, 2026, at 11:59 pm EDT, and get ready to win with AppleVacations. Don't miss this opportunity to claim your romantic escape - enter the AppleVacations Ultimate Romantic Escape to Tulum Sweepstakes today for a free chance to win.
Win $3,950 in value – AppleVacations Ultimate Romantic Escape to Tulum Sweepstakes - Enter Now
Enter the Regal Cinemas Crown Club Hop to It Travel Sweepstakes for a chance to win an unforgettable vacation package. One lucky winner will be randomly selected to receive a 3-day, 2-night getaway for up to four people to the iconic Disneyland® Resort, valued at $7,951.00. Don't miss your opportunity to win this amazing prize - enter to win before the sweepstakes ends at 11:59 p.m. Eastern Time on March 22, 2026, for a free chance to make magical memories with Regal Cinemas.
Win $7,951 in value – Regal Cinemas Crown Club Hop to It Travel Sweepstakes - Enter Now
Enter the Firefighters First Tax Services Disney Giveaway for a chance to win a magical Disney vacation. By using Firefighters First Tax Services, you'll be automatically entered to win a fantastic prize package, including 3-Day Park Passes for up to 4 people, a 4-Night Hotel Stay near the park, and a $1,500 Airfare Credit to either Disneyland in California or Disney World in Florida. Don't miss this opportunity to enjoy the family vacation of a lifetime with Firefighters First Tax Services.
Win $4,500 in value – Firefighters First Tax Services Disney Giveaway - Enter Now
