Vacation Sweepstakes and Giveaways 2026
Win a Free Vacation for Your Family
Found 63 total
Enter the Makenna Koffee Company Dream Hawaiian Vacation Giveaway for a chance to win a 5-day, 4-night trip to Maui! With a grand prize valued at up to $5,500, you could be relaxing on Makena Beach in no time. The prize includes up to $4,500 towards flights and hotel, plus $1,000 in cash for spending money. Enter to win this incredible sweepstakes by September 14th and get ready for the ultimate Hawaiian getaway with Makena Koffee Company!
Win $5,500 in value – Makenna Koffee Company Dream Hawaiian Vacation Giveaway - Enter Now
Get ready to escape in style with the lemme Luxury Vacation Giveaway! Enter to win a stunning prize package consisting of a $20,000 check towards a luxury vacation of your choice and an additional $5,000 cash/check. Don't miss your chance to win this incredible sweepstakes prize, valued at $25,000. Enter now for your free chance to win, but hurry - the contest ends at 11:59:59 p.m. EST on September 30, 2026.
Win $25,000 in value – Lemme Luxury Vacation Giveaway - Enter Now
Enter the Wine Awesomeness Paris Wine + Food Dream Vacation 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 Mama Shelter Paris East, complete with a $300 resort credit. Don't miss your opportunity to win this incredible prize - enter to win a vacation before the sweepstakes ends on 8/31/2026 at 11:59 pm EDT.
Win $1,500 in value – Paris Wine + Food Dream Vacation Sweepstakes - $1500 Value - Enter Now
Enter the Summer Vacation Giveaway from Rebloomed Kids for a chance to win a travel‑ready prize bundle valued at $195. The prize includes a large duffle bag, a top and bottom outfit, a $50 gift card with an Indonesia Culture Kit, and a Five Patch + Hat bundle. The giveaway ends August 3, 2026. Open to U.S. residents 18 years or older. To enter, follow all participating brands, like and share the post to your story, and tag friends in the comments for additional entries.
Win $195 in value – Rebloomed Kids Summer Vacation Giveaway - Enter Now
Get ready to win big in the Petite Keep Gift Card Giveaway! Enter to win an amazing prize package featuring a Grand PK Passport Trunk + Engraved Padlock from Petite Keep, a $350 gift card to shop hats, bags, and more from Kenz Kustomz, and a selection of best-sellers from Vacation Inc. Don't miss your chance to score these fantastic prizes- the giveaway closes August 2nd at 11:59 PM CST. Enter now for a free chance to win!
Win $500 in value – Petite Keep Gift Card Giveaway - Enter Now
Enter the Ecommerce Advisors Big Sur, California Summer Vacay Sweepstakes for a chance to win an unforgettable getaway. One lucky winner will be chosen to receive a grand prize valued at $1500, featuring a 2-night stay at The Treebones Resort and a $250 resort credit. Don't miss out on this incredible opportunity to win a free summer vacay. The vacation sweepstakes ends on 8/31/2026 at 11:59 pm EDT, so be sure to enter to win before time runs out.
Win $1,500 in value – Big Sur California Summer Vacay Sweepstakes - Enter Now
Enter to win the Stellar Partnership Marketing A Royal Romance Getaway to Atlantis Paradise Island, Bahamas! Sweepstakes for a chance to take home an unforgettable grand prize valued at $4472. One lucky winner will receive a 4-day/3-night stay for two at The Cove, Atlantis Paradise Island Bahamas, complete with round-trip private airport transfers and a $450 daily food & beverage credit. Additionally, the winner will receive a $300 Visa Gift Card courtesy of Matador Network. The prize is subject to blackout dates and availability, and must be redeemed within one year of the sweepstakes end date, which is 8/31/2026 at 11:59 pm EDT. Don't miss this opportunity to win a vacation and royal romance getaway.
Enter the Stellar Partnership Marketing Relax and Recharge at The Westin Bayshore, Vancouver! Sweepstakes for a chance to win a grand prize valued at $3000. One lucky winner will receive a 3-night stay for two in a Deluxe Harbourfront Guestroom with daily buffet breakfast and a $200 dining credit. Additional prizes include a $200 gift card from Mode Mobile. The sweepstakes ends on August 31, 2026, at 11:59 pm EDT, and travel must be completed by August 31, 2027, excluding all holidays. Enter to win a vacation and relax in style at The Westin Bayshore, Vancouver!
Win $3,000 in value – Relax & Recharge at The Westin Bayshore Vancouver Trip Sweepstakes - Enter Now
Get ready to win big in the American Humane Society Dream Cancún Vacation Giveaway! Enter to win an incredible $3,675 prize package, featuring a 4-night, all-inclusive stay for four at The Pyramid Cancún. This amazing giveaway also includes 4 $250 flight vouchers courtesy of Frontier Airlines, plus tickets to swim with dolphins at Delphinus Punta Cancún and explore the Interactive Aquarium Cancún. Don't miss your chance to win a vacation. Enter now before the contest ends on August 27, 2026, at 11:59 pm EST. *Scroll on page for the no donation free method form link.
Win $3,675 in value – American Humane Society Dream Cancun Vacation Giveaway - Enter Now
Enter the Journey Switzerland Sweepstakes for a chance to win an unforgettable Swiss travel experience valued at $3,760. One winner and a guest will receive round‑trip international flights, two first‑class Swiss Travel Passes, a panoramic train ride, an exclusive Appenzeller cheese tour, premium sun‑protection gear, Salewa apparel, a SAVEUR market tote, two years of AFAR, SAVEUR and Mountain Gazette subscriptions, and a $150 Visa gift card. The vacation and travel sweeps ends August 21, 2026. Open to legal US residents 21 and older, except those in New York and Florida. Multiple entries are earned by completing actions such as referrals, website visits, and social media engagements.
Win $3,760 in value – Mountain Gazette Journey Switzerland Sweepstakes - Enter Now
