Vacations Sweepstakes
Found 7 total
Say Disney is celebrating the start of summer by gifting one family a $500 Disney gift card that can be used towards park tickets, lightning lanes, dining, and merchandise. This giveaway is open to one winner, who will be announced after Wednesday. The $500 Disney gift card can be used towards Disney vacations, including park tickets, dining, and merchandise. Enter to win this amazing prize by liking and saving this post, and commenting your favorite Disney movie. The giveaway ends on Tuesday, 6/9, and is void where prohibited.
Win $500 in value – Say Disney Disney Gift Card Giveaway - Enter Now
Enter the MSC Cruises 7-Night Caribbean Cruise Sail Into Paradise Cruise Giveaway Sweepstakes, sponsored by OLA Vacations, Inc., for a chance to win a fantastic cruise prize. This exciting giveaway offers a balcony cabin for two on an MSC Cruises 7-Night Caribbean cruise, with an approximate retail value of $3,200. To enter, simply visit the sweepstakes site and complete the entry form, or use the free alternate method of entry by mailing in a 3x5 card with your contact information. The promotion period runs from May 13, 2026, to June 12, 2026, and is open to legal residents of the United States and the District of Columbia who are at least 21 years old. One entry per person is allowed, and the winner will be selected in a random drawing on or about June 22, 2026. Don't miss this opportunity to sail into paradise with OLA Vacations, Inc. and MSC Cruises.
Enter the Sandals Resorts Vacation for Two Sweepstakes, courtesy of Dream Vacations and World Travel Holdings, Inc., for a chance to win a luxurious 5-day, 4-night all-inclusive getaway for two at a Sandals Resort, valued at $4,248. This incredible prize includes a deluxe/luxury category room and ground transfers. To enter to win this amazing prize, simply visit https://www.DreamVacations.com/Contest or https://www.CruiseOne.com/Contest and submit an official entry form by July 13, 2026. A winner will be selected in a random drawing on July 14, 2026. Dream Vacations and World Travel Holdings, Inc. will verify eligibility and compliance with official rules, making this a fair and exciting sweepstakes for all participants, courtesy of Dream Vacations and World Travel Holdings, Inc.
Win $4,248 in value – Sandals Resorts Vacation for Two Sweepstakes - Enter Now
Enter the Best Breckenridge Father’s Day Giveaway 2026 for a chance to win an unforgettable prize package. One grand prize winner will receive a 3-night stay at a Breckenridge Grand Vacations Resorts property, dinner for two at Breckenridge Distillery Restaurant, a VIP distillery tour, 18 holes of golf, and a half-day fishing trip. The total prize value is $2,695. Don't miss out on this amazing giveaway. Submit your free entry before 11:59:00 p.m. MST on 6/21/2026 to win this incredible Breckenridge experience.
Win $2,695 in value – Best Breckenridge Father’s Day Giveaway 2026 - Enter Now
Enter the Apple Vacations PowerReviews Giveaway Sweepstakes for a chance to win a grand prize. The sweepstakes, sponsored by Apple Vacations, begins on May 1, 2026, and ends on July 1, 2026. To enter, leave a review about your booking experience on PowerReviews and fill out the information on the giveaway entry landing page. The grand prize includes a standard resort room for two adults for three nights at any participating RIU property, with an approximate retail value of $2,000. Winner will be selected via random drawing and notified via email. Apple Vacations reserves the right to modify or terminate the sweepstakes at any time. By entering, you agree to the official rules and grant Apple Vacations the right to use your name and likeness for promotional purposes. Enter now for a free chance to win this amazing prize, courtesy of Apple Vacations.
Win $2,000 in value – Apple Vacations PowerReviews Giveaway Sweepstakes - 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 Hilton Grand Vacations Jackpot Sweepstakes for a chance to win a luxurious vacation package to Hawaii, Las Vegas, or Orlando, valued at $18,600. The Grand Prize includes round-trip air, deluxe Hilton accommodations, $1,000 spending money, car rental, and 2,000,000 Hilton Honors Points, or choose $10,000. Plus, 12 Monthly Prizes are up for grabs, each featuring 3 nights at a participating Hilton hotel, 250,000 Hilton Honors points, and $500 spending money, valued at $1,825. Alternatively, monthly winners can opt for $1,000. To enter, visit https://www.hiltongrandvacations.com/lp/sweepstakes, spin the wheel for 50 entries, or use the Alternate Method of Entry. Complete the registration form, follow on-screen instructions, and earn bonus entries by opting-in to marketing messages. With no purchase necessary, enter now for a chance to win big with Hilton Grand Vacations. Monthly winners will be selected on or about the 7th of each month, and the Grand Prize winner on or about February 5, 2027.
Win $40,500 in value – Hilton Grand Vacations Jackpot Sweepstakes - Enter Now
