Vacation Sweepstakes and Giveaways 2026 - Page 5
Found 63 total
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
Enter the Disney Vacation Club Stay Your Way Instant Win Game & Sweepstakes for a chance to win a magical Disney vacation. Celebrating 35 years of Disney Vacation Club, this sweepstakes offers a grand prize of a 6-night Disney Theme Park vacation, where the winner and up to 3 guests can choose between a Walt Disney World Resort or Disneyland Resort getaway. The prize includes a stay in a spacious One-Bedroom Villa, Theme Park tickets, and airfare and ground transportation. Plus, 35 lucky winners will instantly win a $150 Disney Gift Card eGift upon entering. Terms apply. Enter now for a free chance to win with Disney Vacation Club.
Win $18,498 in value – Disney Vacation Club Stay Your Way Instant Win Game & Sweepstakes - Enter Now
Enter the FedEx Vacay Your Way Sweepstakes for a chance to win an unforgettable trip. Choose from four incredible grand prize options, each valued at $12,000: a trip to Paris and Nice, France; Lisbon, Portugal and Barcelona, Spain; Maui and Oahu, Hawaii; or the Turks and Caicos Islands. Each grand prize includes round-trip air transportation, hotel accommodations, and $1,000 in spending money. Additionally, win $5,000, $2,500, or a 3-day/2-night weekend getaway for two to anywhere in the U.S. or Canada, up to $3,200. With FedEx, you could be one step closer to your dream vacation. Enter now for a free chance to win with FedEx.
Win $32,000 in value – FedEx Vacay Your Way 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 to win the Cool Kid Summer Vacation from Macaroni KID Sweepstakes, a fantastic prize package valued at $7,917.76. This exciting giveaway includes a 4-day vacation for up to four people to Walt Disney World Resort, featuring round-trip airfare, ground transportation, and a 3-night stay at a Disney hotel. The prize also includes four 4-Day Walt Disney World Theme Park Tickets with Park Hopper Option, valid until May 31, 2027, and a $300 Disney Gift Card. To be eligible, participants must redeem the prize by May 31, 2027. Note that certain costs and expenses, such as food, beverages, and merchandise, are not included in the prize package and are the sole responsibility of the winner. Don't miss this chance to win a magical summer vacation - enter the Cool Kid Summer Vacation from Macaroni KID Sweepstakes today!
Win $7,917 in value – Cool Kid Summer Vacation from Macaroni KID Sweepstakes - Enter Now
Get ready to win big with the Natura Wines Trek Travel Sweepstakes, a thrilling giveaway from Natura Wines. Enter to win an exciting travel prize package, where two lucky winners will receive a 3-night, 4-day United States travel vacation package for themselves and a guest, valued up to $2500.00. Note that transportation is not included. Don't miss your chance to win this incredible sweepstakes prize - submit your free entry before the deadline at 11:59:59 P.M. MST on May 31, 2026, and you could be enjoying a fantastic trip courtesy of Natura Wines.
Win $2,500 in value – Natura Wines Trek Travel 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
