Vacation Sweepstakes and Giveaways 2026
Vacation Giveaways
Found 69 total
Experience the ultimate getaway with the Visit Grand Rapids Vacation Memories Sweepstakes. Enter between March 5th and August 31st, 2026, for a chance to win exciting prizes. The greater Grand Rapids and Itasca County, Minnesota area is a year-round destination where you can relax, reconnect, and recharge in Minnesota's nature.
Through this sweepstakes, you have two chances to win. First, complete the form and click submit for a chance to win a $250 monthly lodging gift card to a Visit Grand Rapids Lodging Property of your choice. A winner will be drawn each month. Second, share a vacation memory story and upload an image for a chance to win the Grand Prize Trip Package valued at over $1,600. A panel will review all submissions and select a winner, who will be notified on Labor Day 2026.
The Grand Prize Trip Package includes a $500 lodging gift card, dining gift cards, admission to local attractions, and more, totaling $1,750. Enter to win with Visit Grand Rapids, and make unforgettable memories in Minnesota's nature.
Win $1,750 in value – Visit Grand Rapids Vacation Memories Sweepstakes - Enter Now
Enter the Vacationist Missouri Spring Summer Getaway Sweepstakes for a chance to win an unforgettable prize package. The promotion period runs from April 7, 2024, to August 7, 2024. To enter, visit https://vacationistusa.com/missouri-spring-summer-getaway/ and complete the entry form. One entry per person is allowed. The grand prize, valued at $1,335, includes a 2-night stay in St. Louis and a Six Flags Family 4 Pack Vacation Package. Winner will be notified by email and must sign and return an Affidavit of Eligibility and other documents within 5 days. Madden Media, the sponsor, reserves the right to select an alternate winner if necessary. Enter now for a free chance to win this amazing getaway, courtesy of Madden Media.
Win $1,335 in value – Vacationist Missouri Spring Summer Getaway Sweepstakes - Enter Now
Enter the VIP Vacation Newsletter Contest to win a luxurious 7-night getaway for two to Cancun, Mexico. The prize includes a stay at the 5* Dreams Puerto Morelos Resort & Spa, with a Junior Suite featuring a pool view and a King bed. The package also includes round-trip airfare with Air Transat, round-trip transfers, and one checked bag. Valued at approximately $4,400 CAD, including taxes, this free entry sweepstakes is a chance to relax in style. Contest ends July 22, 2026.
Win $4,400 in value – VIP Vacation Newsletter Contest - Enter Now
Enter the News-Press Great Pine Island Experience Matlacha Sweepstakes for a chance to win a dream vacation. Imagine a 2-night stay at Matlacha Tiny Village, breakfast at The Perfect Cup, and appetizers at Yucatan Restaurant. Enjoy 25% off at Onofrio D'Ora Fine Jewelry Boutique and a private visit to Adam's Animal Encounters. This Southwest Florida getaway is worth experiencing. Enter to win by 11:59 p.m. local time on Thursday, May 28, 2026, for a free entry to this incredible prize. The News-Press Great Pine Island Experience Matlacha Sweepstakes is the ultimate giveaway for a unique island experience.
Win $500 in value – News-Press Great Pine Island Experience Matlacha Sweepstakes - Enter Now
Get ready to dive into the trevihydration Pool Season Giveaway and win an amazing prize package. Enter to win a $50 Lululemon eGift Card, Vacation Classic Lotion and Whip, and a variety of Trevi products, including a 20ct Poolside Variety Pack, 20ct Summer Bombsicle, and 20ct Ocean Splash, plus a Trevi Branded Squeeze Bottle. One lucky winner will receive this fantastic prize. Don't miss out on this free entry sweepstakes and your chance to stay hydrated and stylish all season long with Trevi.
Win $100 in value – Trevihydration Pool Season Giveaway - Enter Now
Enter the aerie Memorial Day Giveaway for a chance to win amazing prizes. You could win a $800 Aerie gift card, $500 SUNNYLiFE gift card, JBL Grip speaker, JBL Live 780NC headphones, a Vacation Inc. prize package, and three 12-packs of OLIPOP. To enter, simply like this post, comment with #AerieSweeps, tag a friend, and ensure you're both following @aerie, @vacationinc, @sunnylifeaustralia, @drinkolipop, and @jblaudio.
Win $1,300 in value – Aerie Memorial Day Giveaway - Enter Now
Enter to win the Partner of the Month with Princess Hotels and Resorts, May 2026 Contest for a chance to take home an incredible all-inclusive vacation prize. This amazing sweepstakes giveaway features a 7-night stay at Grand Sunset Princess in Cancun, Mexico, complete with round-trip airfare for two from a Canadian gateway, hotel taxes, land transfers, and an all-inclusive meal plan. The approximate retail value of the prize is $5,070 CDN. Don't miss your chance to win this fantastic prize. Enter now before the contest concludes at 23:59 p.m. ET on May 31, 2026, with Princess Hotels and Resorts.
Superplay Ltd. invites you to participate in the Superplay Anniversary Sweepstakes, a thrilling giveaway where you can win exciting prizes. To enter, simply log into your free Disney Solitaire account via the mobile game app, complete the tutorial phase, and spin the wheel for a chance to earn entries into the sweepstakes. Alternatively, you can submit an email entry to participate. The grand prize winner will receive a fantastic Vacation Package for four nights and five days at Walt Disney World Resort in Orlando, Florida, with a value of approximately $12,857.68. Additionally, 100 winners will receive a $250 Disney Gift Card each. Don't miss this opportunity to win big - enter the Superplay Anniversary Sweepstakes today and get ready to spin your way to amazing prizes. The sweepstakes period runs from May 19, 2026, to June 14, 2026, so be sure to participate before the deadline. Superplay Ltd. wishes you the best of luck in this exciting sweepstakes.
Email Entry: To enter without need to play games or complete the tutorial phase in the App, once every four (4) hours during the Sweepstakes Period, you may send an email to [email protected] with the subject line “Anniversary Sweepstakes Email Entry” and the following information in the body of the email: User ID, request to enter without need to play or complete the tutorial phase. Upon sending the email, you will be granted a random number of entries out of the following possibilities 5, 7, 8, 10, 12, 15, 25, 100. You will receive a reply email indicating the number of entries you have been awarded, which is determined by the same random means applicable to App-based entries. Each email you submit is a Gameplay. Email Entry submissions count toward the daily limit of six (6) total Gameplays per person per day (as defined above). Email Entry does not require completing the Disney Solitaire tutorial or creating an Account in the App. Any attempt to submit more than one (1) Email Entry every four (4) hours will be rejected.
Win $37,587 in value – Superplay Anniversary Sweepstakes - Enter Now
Get ready to win big with LD Cigarettes Sun’s Out, Fun’s In Instant Win Game Sweepstakes. Enter now for a chance to score amazing prizes, including gift cards and a dream vacation for two. With 1,381 winners, you could be one of the lucky ones to take home instant win prizes like Amazon, Starbucks, or Apple eGift Cards, or even the grand prize - a 3-day, 3-night trip to a destination of your choice, valued at $5,000. To enter, simply participate in the daily entry sweepstakes, Don't miss out, enter by June 29, 2026, and visit LD Cigarettes for the official rules. Enter to win with LD Cigarettes.
Win $47,375 in value – LD Cigarettes Sun’s Out, Fun’s In Instant Win Game Sweepstakes - Enter Now
Enter the Sandals Resorts Vacation for Two Sweepstakes, courtesy of Dream Vacations and World Travel Holdings, Inc., for a chance to win a luxurious 5-day, 4-night all-inclusive getaway for two at a Sandals Resort, valued at $4,248. This incredible prize includes a deluxe/luxury category room and ground transfers. To enter to win this amazing prize, simply visit https://www.DreamVacations.com/Contest or https://www.CruiseOne.com/Contest and submit an official entry form by July 13, 2026. A winner will be selected in a random drawing on July 14, 2026. Dream Vacations and World Travel Holdings, Inc. will verify eligibility and compliance with official rules, making this a fair and exciting sweepstakes for all participants, courtesy of Dream Vacations and World Travel Holdings, Inc.
Win $4,248 in value – Sandals Resorts Vacation for Two Sweepstakes - Enter Now
