Vacation Sweepstakes and Giveaways 2026

Emily Kaufman is giving away a two‑night oceanfront suite, dinner for two at Ocean 2000 on the property, and a couples massage, with entries closing Friday at 3 p.m. PST.

Yamas Greek Kitchen + Bar is giving a dream vacation for two to Rhodes, Greece, in June 2026, including round trip flights and a 7 night stay. Runs December 2, 2025, through February 2, 2026.

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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.

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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.

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.

You could win a three‑night, all‑inclusive stay for two in a Junior Ocean View Suite at Pueblo Bonito Sunset Beach Golf & Spa Resort, along with a spa treatment for two at the award‑winning Armonia Spa. Additional prizes include a PINCHme Vacation Box valued at $200, a $150 Scojo New York gift card, and two LifeStraw Go Series travel water filter bottles with Sip Filter Straws valued at $190.

Quebec Maritime is offering an unforgettable getaway: a snowmobile vacation for four through Bas‑Saint‑Laurent and Gaspésie. The prize includes stays at charming hotels and lodges, complete with dinners and breakfasts at each stop from Domaine Valga in Saint‑Gabriel‑de‑Rimouski to Riôtel Matane and more. With a total value of CAN$5,500 (US$3,950), entries close on March 31, 2026, at 11:59 PM EDT.

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The DreamVacations Princess Cruises Sweepstakes prize consists of a World Travel Holdings (Dream Vacations or CruiseOne) Princess Cruises 7‑night Caribbean cruise, with a maximum value of up to $5,000 USD. Airfare, insurance, airport transfers, additional nights, and optional excursions are not included and are the sole responsibility of the winner. The winner is also responsible for all costs related to passports, visas, gratuities, and personal expenses. The prize must be claimed and the vacation booked for travel by April 30, 2026, with sailing completed by February 28, 2027. 

The Grand Prize Winner will receive one of the following prize options (the “Grand Prize”). Option 1 consists of a 2025 Chevrolet Tahoe High Country (ARV $95,000 USD), a $10,000 USD check, and travel for the winner and guest(s) to a destination vacation of their choice, domestic or international, valued up to $10,000 USD. Alternatively, Option 2 consists of a cash prize in the form of an $80,000 USD check.

KTRK Television, Inc. is giving one winner the ultimate escape, a seven‑night Disney Cruise Line vacation aboard the Disney Treasure for up to four people, complete with round-trip airfare, a night at a Walt Disney World® Resort hotel, ground transportation, meals, gratuities, and more. Valued at $14,369.12, this unforgettable journey closes on January 18, 2025, at 11:59 PM CST.