Vacation Sweepstakes and Giveaways 2026
Vacation Giveaways
Found 47 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 AARP (AMOE) Royal Caribbean Sweepstakes for a chance to win a grand prize. Five lucky winners will each receive a $500 Royal Caribbean gift card, perfect for booking a dream cruise vacation. To redeem, simply book your cruise online at http://www.RoyalCaribbean.com or call 866-504-3941, then follow the redemption instructions. The total prize value is $2,500. Don't miss this opportunity to win a free Royal Caribbean gift card and start planning your next adventure with Royal Caribbean.
Win $2,500 in value – AARP (AMOE) Royal Caribbean 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 the KrollTravel Explore the World Giveaway to win an exciting 'Explore the World' Prize Pack. This fantastic sweepstakes offers a chance to win a collection of four culinary and travel books, valued at $200, to inspire your next adventure. The prize pack includes a Dining Guide to Paris, France, Best Getaways in North America, Asian Cooking, and World's Best Eco-Lodges & Hotels. Get free entry to win this amazing prize and start planning your dream vacation with KrollTravel.
Win $200 in value – KrollTravel Explore the World Giveaway - Enter Now
Get ready to glow with the Bulletproof Red Light Therapy Mask Giveaway. Enter to win a prize that will take your spring wellness routine to the next level. To participate, simply like this post, follow @bulletproof on Instagram, and comment with your dream spring vacation destination and favorite Bulletproof product. With a free entry, you'll have a chance to win and nourish your body from the inside out this season, courtesy of Bulletproof.
Win $89 in value – Bulletproof Red Light Therapy Mask Giveaway - Enter Now
Get ready to win big with the Bitchin’ Sauce Spring Break Giveaway. Enter to win an epic prize pack featuring a 10-pack of Bitchin' Sauce, a saucy pool float, a vibey frisbee, and new Bitchin' Chips. You'll also score Original Coconut Oil SPF 15 from Vacation, 15 cans of Slice, and a pair of stylish shades from Knockaround. Don't miss out - enter for your chance to win before the sweepstakes ends on 4/3/26 at 12 PM PST.
Win $200 in value – Bitchin’ Sauce Spring Break Giveaway - Enter Now
Enter the Honeycomb Retreats 2 Night Stay Giveaway for a chance to win an unforgettable prize package. You could win a free 2-night stay at the Hilltop Hideaway at Smith Lake, a YETI Camino Bag, Vacation Classic Whip SPF, and Turkish Towels. The total prize is up for grabs, and the winner will be announced on May 1, 2026. Don't miss this opportunity to enter to win and make your dream getaway a reality with Honeycomb Retreats.
Win $600 in value – Honeycomb Retreats 2 Night Stay Giveaway - Enter Now
Enter the Overlook Cabin Rentals Cabin Giveaway for a chance to win a free 3-night stay at our newly renovated Bearfoot Pines cabin, boasting a 4.9 rating on Airbnb, Vrbo, BDC, and Direct. With brand new furniture, design, décor, coffee bar, mural, and more, this cabin is the perfect getaway. Overlook Cabin Rentals is excited to give away this incredible prize, so enter to win and make your dream vacation a reality with Overlook Cabin Rentals.
Win $1,000 in value – Overlook Cabin Rentals Cabin Giveaway - Enter Now
Caden Lane and Pipette Baby are giving away the ultimate vacation bundle in their Vacation Ready Giveaway. One lucky winner will receive a $200 Caden Lane Gift Card and Pipette's spring break essentials, including Mineral Sunscreen SPF 50, Baby Lotion, Calming Balm, Skin Rescue Spray, and Baby Shampoo Wash. Enter to win this amazing prize bundle by following the instructions. The giveaway ends on April 4th and is open to individuals 18 years and older. This is a free entry sweepstakes with one winner. Enter to win and get ready for your next vacation.
Win $200 in value – Caden Lane and Pipette Baby Vacation Bundle Giveaway - 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
