Vacation Sweepstakes and Giveaways 2026 - Page 5
Found 69 total
The Traveling Steph is celebrating their one-year anniversary with an exciting giveaway. Enter for a chance to win a $500 Disney Gift Card and $200 toward merchandise and travel services. One winner will be announced on May 16th. This sweepstakes is a great opportunity to win a fantastic prize and make your Disney vacation dreams come true. Enter now for your free chance to win.
Win $700 in value – The Traveling Steph Disney Gift Card Giveaway - Enter Now
Enter the Maryland Lottery St. Petersburg Luxury Resort Vacation Second Chance Giveaway for a chance to win an unforgettable 4-night luxury stay at The Vinoy Resort & Golf Club in downtown St. Petersburg, Florida. This incredible prize package for two includes hotel accommodations with daily breakfast, roundtrip airfare, spa or golf experiences, and $1,000 in spending money. With an estimated prize value of $17,362.45, this is an opportunity you won't want to miss. Simply enter to win and you could be randomly drawn as the lucky winner. Don't wait - enter the Maryland Lottery St. Petersburg Luxury Resort Vacation Second Chance Giveaway before the contest ends on Tuesday, July 6, 2026.
Enter the Viking Q2 2026 2027 8-Day Journey Sweepstakes for a chance to win an incredible 8-day cruise for two, complete with airfare. This free entry sweepstakes is open to residents of the 50 U.S. states, D.C., and Canada, excluding Quebec. To enter, simply submit your entry online, by mail, through a webinar, or on Facebook/Instagram. One lucky winner will be selected in a random drawing on August 7, 2026, to receive a grand prize valued up to $40,588 CAD. The prize includes a choice of cruises, such as the Paris Heart of Normandy or Nordic Wonders, with all expenses covered. Don't miss this opportunity to win a dream vacation with Viking River Cruises. Enter now through June 30, 2026.
Win $26,988 in value – Viking Q2 2026 2027 8-Day Journey Sweepstakes - Enter Now
Enter to win the ultimate getaway in The Sandals and Beaches Giveaway Q2, 2026 Sweepstakes. One lucky Grand Prize Winner will receive a 4-day/3-night "All-Inclusive" vacation package for two to a Sandals Resort or Beaches Resort of their choice, with a prize value of $3,054 - $3,538USD. The prize includes a Deluxe Suite, "All-Inclusive" amenities like food, beverages, and activities, and local airport transfers. Note that airfare is not included and the winner must redeem the prize within the specified time period. The winner and their travel companion must obey local laws and are responsible for expenses not expressly stated in the package. Enter now for a chance to win this incredible prize, courtesy of Sandals and Beaches.
Win $3,583 in value – Sandals and Beaches Giveaway Q2, 2026 Sweepstakes - Enter Now
Enter the Hawaii.com Oʻahu Family Vacation Sweepstakes for a chance to win an unforgettable prize package for up to four travelers. This incredible giveaway includes a 4-night stay at ʻAlohilani Resort Waikīkī Beach, private SUV airport transportation, and exciting activities like a Polynesian Cultural Center Aliʻi Lūʻau Package, Dolphin Snorkel Tour, UTV Raptor Adventure Tour, and a "Distiller for a Day" Deep Dive Tour. Plus, enjoy a $200 dinner gift card. The total prize value is approximately $5,700. Don't miss this opportunity to win a free family vacation in Oʻahu - enter the Hawaii.com Oʻahu Family Vacation Sweepstakes today.
Win $5,700 in value – Hawaii Oahu Family Vacation Sweepstakes - Enter Now
Enter the Golf PEI Golf Vacation Giveaway Contest today for your chance to win an incredible PEI golf vacation valued at $10,000. This grand prize pack includes $7,500 in Golf PEI gift cards for golf rounds and accommodations, $1,000 in gift cards to Prince Edward Island restaurants, a $1,000 rental car voucher, $500 in Island activities, and 4 tickets to the 2027 Charlottetown Festival. Enter to win this amazing prize for free. Contest ends October 31, 2026.
Win $10,000 in value – Golf PEI Golf Vacation Giveaway Contest - Enter Now
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 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 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
Enter the Disney Vacation Club Stay Your Way Instant Win Game & Sweepstakes for a chance to win a magical Disney vacation. Celebrating 35 years of Disney Vacation Club, this sweepstakes offers a grand prize of a 6-night Disney Theme Park vacation, where the winner and up to 3 guests can choose between a Walt Disney World Resort or Disneyland Resort getaway. The prize includes a stay in a spacious One-Bedroom Villa, Theme Park tickets, and airfare and ground transportation. Plus, 35 lucky winners will instantly win a $150 Disney Gift Card eGift upon entering. Terms apply. Enter now for a free chance to win with Disney Vacation Club.
Win $18,498 in value – Disney Vacation Club Stay Your Way Instant Win Game & Sweepstakes - Enter Now
