Vacation Sweepstakes and Giveaways 2026
Vacation Giveaways
Found 63 total
TikTok_kels_9 is hosting a Summer Vacation Giveaway where one winner will be chosen on May 29th. To enter, follow the account, post, and comment where you'd like to vacation this summer. This exciting sweepstakes offers a chance to win a free vacation. Enter to win and tell your friends for a chance to make your summer dreams come true. One winner will be selected, and the giveaway is open until May 29th.
Win $100 in value – TikTok_kels_9 Summer Vacation Giveaway - Enter Now
Enter the Regal Crown Club Ultimate AutoCamp Vacation Sweepstakes, sponsored by Regal Cinemas, Inc., for a chance to win a 2-night stay in a premium custom Airstream Suite at any AutoCamp location, valued at $1,100. The sweepstakes begins on May 7, 2026, and ends on June 4, 2026. To enter, Regal Crown Club members can swipe or scan their card, enter their card number online, or use their Unlimited Subscription Program pass. Alternatively, enter via the Regal Crown Club Reward Center, email, or social media. Limit 10 entries per day. To enter via e-mail: E-mail your full name, phone number and Regal Crown Club card number (if any) to [email protected] and include “Ultimate AutoCamp Vacation” in the subject line of your e-mail. Regal Cinemas, Inc. is the sole sponsor of the sweepstakes. No purchase necessary to enter or win. Enter now for a free chance to win a fantastic vacation prize, courtesy of Regal Cinemas, Inc.
Win $1,100 in value – Regal Crown Club Ultimate AutoCamp Vacation Sweepstakes - Enter Now
Fairytale Travel Planner is excited to announce a Disney Giveaway for all Disney lovers. One lucky winner will receive a $50 Disney Gift Card, a Simple Modern Tumbler, and a Portable Cooling Fan. Whether you're planning a magical family vacation, a couples getaway, or your little one's first Disney trip, this giveaway is for you. Enter to win by following Fairytale Travel Planner, liking and sharing this post, and tagging your Disney-loving friends in the comments. Unlimited entries are allowed, and the winner will be randomly selected on May 14th EST. Good luck to all participants in this fun Disney sweepstakes giveaway.
Win $50 in value – Fairytale Travel Planner Disney Giveaway - Enter Now
Enter the Walt Disney World National Keyword Contest, a sweepstakes giveaway conducted by Audacy Operations, LLC, for a chance to win a magical grand prize vacation package. The prize includes a 3-night stay at a Walt Disney World Resort hotel, 4-Day Walt Disney World Theme Park Tickets with Park Hopper Option, roundtrip airfares, and a $1000 Disney Gift Card, valued at approximately $8,617.76, courtesy of Disney Destinations, LLC. To enter, listen to participating Audacy radio stations from May 11 to May 29, 2026, for the hourly keyword announcement, then fill out the "Enter to Win" form on the station's website. Open to US residents 21+ in the 48 contiguous states and DC. One entry per email address per contest play, with a maximum of three entries per day. Winner will be randomly selected on June 1, 2026. Audacy Operations, LLC, is the contest administrator, and Disney Destinations, LLC, is the sponsor. No purchase necessary to enter or win. Void where prohibited. *Station list at bottom of page.
Win $8,618 in value – Walt Disney World National Keyword Contest - Enter Now
Enter the HEYDUDE Vacation Giveaway for a chance to win exciting prizes. At HEYDUDE, we appreciate hard work and think it's time for a break. To enter, follow @heydude, like this post, and tag someone who deserves a vacation, sharing why. For a bonus entry, share this post to your Story. Three winners will receive prizes, including a $1,500 Airbnb gift card, HEYDUDE products, a $500 HEYDUDE gift card, and a $250 HEYDUDE gift card. No purchase necessary, open to 18+ US (continental) residents. The giveaway ends 5/17/26 at 11:59PM ET. See Official Rules (link in bio) for details, courtesy of HEYDUDE.
Win $2,300 in value – HEYDUDE Vacation Giveaway - Enter Now
Enter the Holiday World May 2026 Rubber Duck Days Ultimate Giveaway, a thrilling sweepstakes by Holiday World & Splashin' Safari. NO PURCHASE NECESSARY. Sign up via Quikly, respond quickly to notifications, and win prizes like a Family Vacation Package, tickets, or discounts. Top prize: a Family Four Pack of Two-Day Tickets, a two-night stay in a Holiday Cottage, and a Mountain Dew KanJam set ($478 + $133.72 value). Enter by May 26th, 2026. Visit https://www.quikly.com/q/wbMhmxN to participate. Holiday World & Splashin' Safari brings you this exciting giveaway, with prizes delivered via website, email, or text.
Win $611 in value – Holiday World May 2026 Rubber Duck Days Ultimate Giveaway - Enter Now
Get ready for adventure with the Eddie Bauer Adventure Club The Red Rocks and Roam Giveaway. Enter to win exciting prizes, including a Grand Prize package valued at up to $9,000, featuring a 7-night vacation for four at Club Wyndham Moab Resort in Moab, Utah, a $2,000 Airline Credit, and a $1,000 Virtual Promotional Prepaid Mastercard. Monthly and Weekly Prizes are also available, with twelve $750 Virtual Promotional Prepaid Mastercards and fifty-two $250 Virtual Promotional Prepaid Mastercards up for grabs. With a total ARV of $25,945, this free entry sweepstakes is a thrilling opportunity to win big. Prizes are non-transferable, and winners are responsible for all taxes. Join the Eddie Bauer Adventure Club and take a chance to win with this incredible giveaway from Eddie Bauer.
Win $25,945 in value – Eddie Bauer Adventure Club The Red Rocks and Roam Giveaway - Enter Now
Enter to win the SweetsAndSavory Italian Food Tour Vacation Sweepstakes for a chance to claim a $10,000.00 prize. One lucky winner will receive the prize by check or other form within 30 days of returning the completed and valid affidavit. With only one prize available, don't miss this opportunity to win big in this exciting giveaway.
Win $10,000 in value – Sweets and Savory Italian Food Tour Vacation Sweepstakes - Enter Now
Enter the Apple Vacations AV X Amstar Dominican Republic Getaway sweepstakes for a chance to win an unforgettable 4-night getaway for two to the Dominican Republic. Valued at a significant amount, the Grand Prize includes roundtrip air for two, a 4-night stay at a participating RIU resort, an Amstar shared excursion gift certificate, and private transfers. Apple Vacations and Amstar DMC invite you to enter to win this incredible prize and make memories in paradise. One lucky winner will be selected, so enter now and start dreaming of your next escape with Apple Vacations.
Win $2,500 in value – Apple Vacations AV X Amstar Dominican Republic Getaway - Enter Now
Enter the Habit Burger and Grill Habit Ranch Sweepstakes for a chance to win a free 2-night vacation rental at the Habit Ranch. The Habit Burger & Grill Habit Ranch Sweepstakes is open to MyHabit rewards program account holders, 18+ (19+ in AL and NE), and legal US residents. To enter, follow the link in the email invitation or register for a free MyHabit rewards account. Submit your entry by May 18, 2026, for a chance to win a $4,995 vacation rental for up to 8 people. The Grand Prize includes a 2-night stay at The Outlaw House in Pioneertown, CA, but transportation is not included. The Habit Restaurants, LLC, is the sponsor of this sweepstakes, and the winner will be selected randomly on May 19, 2026. Enter now for a chance to win with The Habit Burger & Grill Habit Ranch Sweepstakes.
Win $4,995 in value – Habit Burger & Grill Habit Ranch Sweepstakes - Enter Now
