Vacation Sweepstakes and Giveaways 2026
Vacation Giveaways
Found 69 total
Enter the Grand Circle Corporation 2026 Summer Vacation Ambassador Referral Sweepstakes for a chance to win a grand prize of $6,500 in cash or travel credits. Sponsored by Grand Circle LLC, this sweepstakes is open to legal US residents, excluding CO, FL, NY, and RI, who are 18+ years old. No purchase necessary, and odds of winning depend on the total number of eligible entries. To enter, refer a new customer to book a trip with Grand Circle between April 26 and July 15, 2026, or mail a postcard with required information to Grand Circle LLC by July 15, 2026. Ten winners will be selected in a random drawing on July 27-31, 2026. Winners will receive their choice of cash or travel credits, with a total prize value of $6,500 or $3,500. Grand Circle is responsible for shipping the prize, but winners are responsible for taxes and fees. Enter now for a chance to win a dream vacation, courtesy of Grand Circle Corporation 2026 Summer Vacation Ambassador Referral Sweepstakes.
Get ready to win an unforgettable experience with the Ocean City New Jersey Free Family Vacation Contest. Enter to win a fantastic 7-night getaway to Ocean City, New Jersey, courtesy of the Ocean City Tourism Commission. One lucky winner will be selected on or about Monday, July 6, 2026, to enjoy a free vacation in a stunning 3-bedroom, 2-bathroom OCNJ Condo, perfect for a family of up to 8 people. The prize includes 7 nights of accommodations, from Saturday to Saturday, in a great location within walking distance of the beach. Enter now for a chance to create lifelong memories with your loved ones in Ocean City, New Jersey, with the Ocean City Tourism Commission.
Win $4,000 in value – Ocean City New Jersey Free Family Vacation Contest - Enter Now
Enter the cksquared_boutique May Giveaway for a chance to win an incredible 4-night, 5-day all-inclusive getaway to Sandals Barbados resort or a cash alternative of $4,000 plus a $1,000 CK shopping spree. This amazing sweepstakes offers a free entry to win a prize valued at over $5,000. Don't miss out on this opportunity to win big and indulge in a luxurious vacation or a cash prize and shopping spree with cksquared_boutique.
Win $6,000 in value – CKsquared Boutique May Giveaway - Enter Now
Enter the VisitFortMyers You Deserve a Shell-cation Giveaway for a chance to win a fantastic Grand Prize. One lucky winner will receive a three-night stay for up to four people at the Sundial Beach Resort & Spa in Sanibel, FL, complete with a two-bedroom Garden View unit and access to resort recreation like bikes, kayaks, and paddleboards. The prize also includes a $2,000 pre-paid Visa Gift Card for travel and expenses. With an approximate retail value of $4,830, this giveaway is an opportunity you won't want to miss. Enter to win this incredible prize and make your dream vacation a reality with VisitFortMyers.
Win $4,830 in value – VisitFortMyers You Deserve a Shell-cation Giveaway Sweepstakes - Enter Now
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
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.
