Vacation Sweepstakes and Giveaways 2026
Vacation Giveaways
Found 54 total
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 Vacations By Crystal Gift Card Giveaway for a chance to win exciting prizes. You could win a $50 Visa/Mastercard gift card, a vacation-themed Tumbler, and a vacation-themed T-shirt. Don't miss out on this free entry sweepstakes. Submit your entry before the deadline of 4/2/2026.
Win $100 in value – Vacations By Crystal Gift Card Giveaway - Enter Now
Get ready to win big in the DJ Matlock Vacation Destination Giveaway, an exciting sweepstakes where one lucky winner will receive an unforgettable prize package. This incredible giveaway includes a vacation destination of their choice from a wide range of amazing options, plus free DJ services from DJ Matlock for up to 4 hours. Enter to win this amazing prize, valued at a unique experience, by the deadline to be announced on April 1st. Don't miss your chance to make your celebration unforgettable with DJ Matlock.
Win $2,100 in value – Dj Matlock Vacation Destination Giveaway - Enter Now
Get ready to win big with the WHUT Howard University Television Disney World Sweepstakes, courtesy of 96.3 WHUR and WHUT-TV. Enter to win a magical 3-night Walt Disney World Resort vacation package for four, valued at $7,617.76. To participate in this exciting giveaway, simply visit the WHUR-FM or WHUT-TV website and submit your entry between March 25, 2026, and April 30, 2026. Open to Maryland, Virginia, and DC residents, 21+, this free entry sweepstakes offers a chance to create unforgettable memories. One grand prize winner will be randomly selected from eligible entries. Sponsored by 96.3 WHUR, a Howard University Radio Network company, with no purchase necessary, making it easy to enter and win with WHUT Howard University Television Disney World Sweepstakes.
Win $7,617 in value – WHUT Howard University Television Disney World Sweepstakes - Enter Now
Enter the Map & Magic Travel Gift Card Giveaway for a chance to win a $250 Disney Gift Card and free custom vacation planning services. This amazing prize package is valued at a magical experience for one lucky family. To be eligible, simply participate before the deadline. The winner will be announced on Wednesday, April 1st, so act now and take a shot at making your next trip unforgettable with Map & Magic.
Win $250 in value – Map and Magic Travel Gift Card Giveaway - 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
Enter the Gracie Barra Layton 5-night Luxury Hawaii Hotel Stay Giveaway for a chance to win a luxurious 5-night stay in Hawaii. This incredible sweepstakes offers a free entry to win a dream vacation. The giveaway ends on 3/31/2026, so be sure to enter before the deadline. Gracie Barra Layton is giving away this amazing prize; don't miss your opportunity to win a luxury hotel stay in beautiful Hawaii.
Win $3,600 in value – Gracie Barra Layton 5-night Luxury Hawaii Hotel Stay Giveaway - Enter Now
Enter the ZipString Ultimate Orlando Family Trip Giveaway for a chance to win an unforgettable family adventure. The grand prize package, valued at approximately $10,000 USD, includes round-trip airfare for up to 4 travelers, hotel accommodations for up to 5 nights, theme park admission, and a spending allowance. With ZipString, you can enjoy a stress-free family vacation, courtesy of their Ultimate Orlando Family Trip Package. Don't miss this opportunity to create lifelong memories with your loved ones, courtesy of ZipString.
Win $10,000 in value – ZipString Ultimate Orlando Family Trip Giveaway - Enter Now
Enter the FedEx Vacay Your Way Sweepstakes for a chance to win an unforgettable trip. Choose from four incredible grand prize options, each valued at $12,000: a trip to Paris and Nice, France; Lisbon, Portugal and Barcelona, Spain; Maui and Oahu, Hawaii; or the Turks and Caicos Islands. Each grand prize includes round-trip air transportation, hotel accommodations, and $1,000 in spending money. Additionally, win $5,000, $2,500, or a 3-day/2-night weekend getaway for two to anywhere in the U.S. or Canada, up to $3,200. With FedEx, you could be one step closer to your dream vacation. Enter now for a free chance to win with FedEx.
Win $32,000 in value – FedEx Vacay Your Way Sweepstakes - Enter Now
Enter the PigeonForgeChamber Spring in the Smokies Giveaway for a chance to win an exciting prize package. One Grand Prize winner will receive a fantastic bundle, including a 2-Night Stay at Cedar Lodge 605 from Smoky Mountain Escapes Vacation Rentals, gift certificates to top spots like Brick & Spoon, Dick's Last Resort, Ole Red Gatlinburg, and Three Bears General Store, plus tickets to thrilling attractions such as the Array Variety Show, Wonderworks, and NASCAR SpeedPark, as well as a Half Day Hike for 2 with A Walk in the Woods and wristbands for Pigeon Forge Snow. Don't miss this free entry sweepstakes to win big and experience the best of the Smokies.
Win $1,000 in value – PigeonForgeChamber Spring in the Smokies Giveaway - Enter Now
