Vacation Sweepstakes and Giveaways 2026 - Page 5
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Get ready to embark on a journey of a lifetime with the Expedia Cruises Win a Dream Vacation 2026 Sweepstakes! Enter to win an incredible Rocky Mountaineer Vacation for two, valued at up to $8,000, complete with airfare included. This ultimate getaway is courtesy of Expedia Cruises™. Don't miss your chance to win - enter now for free! Sweepstakes ends at 11:59 pm PST on Sunday, November 1, 2026. Expedia Cruises™ is giving you the opportunity to make your dream vacation a reality.
Win $8,000 in value – Expedia Cruises Win a Dream Vacation 2026 Sweepstakes - Enter Now
Enter to win the CruiseOne $10,000 Vacation Sweepstakes for a chance to score a $10,000 travel credit with World Travel Holdings. This incredible prize can be applied to a new cruise, tour, or resort vacation with CruiseOne or Dream Vacations, covering costs like cabin fare, taxes, and gratuities. Eligible trips include those with featured cruise lines or preferred partners like American Airlines Vacations and Sandals Resorts. With no cash value, this prize must be redeemed by December 15, 2026, and is subject to additional terms. Courtesy of CruiseOne, this free entry sweepstakes offers a thrilling opportunity to win a dream getaway valued up to $10,000 USD with World Travel Holdings, specifically through CruiseOne.
Win $10,000 in value – CruiseOne $10,000 Vacation Sweepstakes - Enter Now
Enter the DreamVacations $10,000 Vacation Sweepstakes for a chance to win a $10,000 travel credit with World Travel Holdings. This exciting prize can be applied to a new cruise, tour, or resort vacation booking with Dream Vacations or CruiseOne, covering costs like cabin fare, taxes, and gratuities. Eligible trips include those with featured cruise lines or preferred partners like American Airlines Vacations and Sandals Resorts. The credit, valid until December 15, 2026, has no cash value and is subject to additional terms. Join the sweepstakes with World Travel Holdings, including Dream Vacations, for a free entry to win this incredible $10,000 prize.
Win $10,000 in value – DreamVacations $10,000 Vacation Sweepstakes - Enter Now
Enter the Visit Orlando Family Vacation Sweepstakes for a chance to win an unforgettable getaway. The grand prize is a five-day, four-night trip to Orlando for you and up to three guests, valued at $4,359.92. This incredible prize package includes Frontier Airlines flight vouchers, a four-night stay at the DoubleTree by Hilton at SeaWorld, multi-day admission to SeaWorld Orlando and Aquatica, meal vouchers, and a full-size rental vehicle. Travel with ease, courtesy of Visit Orlando, and enjoy a stress-free family vacation. Don't miss out on this amazing opportunity to create lasting memories with your loved ones, courtesy of Visit Orlando.
Win $4,360 in value – Visit Orlando Family Vacation Sweepstakes - Enter Now
Enter the JetBlue Vacations Win a Trip to Universal Orlando Resort Sweepstakes for a chance to win an unforgettable Orlando getaway. One lucky group of four will score an incredible prize package, courtesy of JetBlue Vacations and Universal, including round-trip flights on JetBlue, hotel accommodations at the Terra Luna Resort, ground transportation, and admission to Universal Studios Florida, Islands of Adventure, Epic Universe, and Volcano Bay. Don't miss your chance to win this amazing prize, valued at thousands, with a free entry. The sweepstakes closes on April 30, 2026, at 11:59 PM ET, so enter to win now with JetBlue Vacations.
Enter the Breckenridge Epic Getaway 2025-2026 Sweepstakes for a chance to win an unforgettable prize package. One Grand Prize winner will receive a five-night stay at a Breckenridge Grand Vacations property, four Epic Day Passes for non-peak dates during the 2026-2027 ski season, $5,000 in cash, and four pairs of Glade Optics goggles, valued at approximately $10,248. Join Breckenridge Grand Vacations for this exciting giveaway and take a shot at winning big with a free entry. Breckenridge Grand Vacations brings you this amazing sweepstakes opportunity.
Win $10,248 in value – Breckenridge Epic Getaway 2025-2026 Sweepstakes - Enter Now
Enter the Sandals and Beaches Giveaway Q1, 2026 Sweepstakes for a free 4-day/3-night all-inclusive vacation for two to a Sandals or Beaches Resort. Win a grand prize valued at a luxurious getaway, excluding select locations, with travel to be completed within a year. Sweepstakes ends April 10, 2026. The Prize drawing will be conducted on or about April 10, 2026. The potential Sandals and Beaches winner will be contacted by the Sponsor via phone, email and/or USPS mail.
Win $3,054 in value – Sandals and Beaches Giveaway Q1, 2026 Sweepstakes - Enter Now
The Word KFIA is sending one winner on an unforgettable journey, an Italy Unfiltered trip for two, running September 29 to October 8, 2026. The prize includes 4‑star accommodations, guided tours, entrance fees, daily breakfasts, four dinners with wine or beer, and all hotel taxes and service charges, valued at $9,990 USD. The Word KFIA The Italy Unfiltered Dream Vacation Sweepstakes entries close August 31, 2026, at 9:59 PM PDT.
Win $9,990 in value – The Word KFIA The Italy Unfiltered Dream Vacation Sweepstakes - Enter Now
The Word Miami is offering an unforgettable adventure. One grand prize winner will enjoy the Italy Unfiltered trip for two, running September 29 – October 8, 2026. The prize package includes 4‑star accommodations, expert local guides, daily breakfasts, select dinners with wine or beer, entrance fees, and all the extras that make travel seamless from baggage handling to hotel tips. The Word Miami The Italy Unfiltered Dream Vacation Sweepstakes entries close September 1, 2026, at 12:59 AM EDT.
Win $9,990 in value – The Word Miami The Italy Unfiltered Dream Vacation Sweepstakes - Enter Now
Philadelphia’s AM 990 The Answer is giving one lucky winner the Italy Unfiltered trip for two, set for September 29 – October 8, 2026. The prize features four‑star accommodations, expert‑led tours, daily breakfasts, four dinners with wine or soft drinks, and all the extras from entrance fees to hotel tips, a package valued at $9,990 USD. Airfare to Rome is not included, and entries close September 1, 2026, at 12:59 AM EDT.
