Activities Hobbies US Vacation Sweepstakes Lots of sweepstakes giving away trips within the United States. Share PINTEREST Email Print Enter these vacation sweepstakes and you could be packing your bags and taking a free trip. Image © Jasper White / Getty Images. Hobbies Contests Dream Vacations Basics Tips and Tricks Win Money Win Electronics Home and Garden Lotteries Win Vehicles Jewelry and Clothing Types of Contests Creative Contests Scams Couponing Freebies Frugal Living Fine Arts & Crafts Astrology Card Games & Gambling Cars & Motorcycles Playing Music Learn More By Sandra Grauschopf Sandra Grauschopf Facebook Twitter Writer University of Maryland Sandra Grauschopf has been working in the contests industry since 2002. She is a passionate sweeper, with tens of thousands of dollars worth of prize wins to her name, and she has been sharing advice about how to be a winner for over a decade. Learn about our Editorial Process Updated on 09/28/22 Have you ever dreamed of walking down the red carpet at a Hollywood premiere? Or of spending a cozy weekend watching the fall foliage with a loved one? Vacation sweepstakes can offer you all of these experiences and more, absolutely free. Enter these sweepstakes for your chance to win a dream vacation. International Travel Sweepstakes list. You can also enter to win free Disney vacations on the Disney Sweepstakes list, free cruises on the Cruise Sweepstakes List, trips to Hawaii with the Hawaii Sweepstakes List, or trips to Las Vegas on the Free Vegas Vacation Sweepstakes List. 1. Roxy - Waikiki SweepstakesGet the chance to win a five-night getaway for two people to Hawaii.Entry Frequency: One time per person/email/householdEnd Date: September 30th, 2022Eligibility: Open to the U.S. and CanadaMore Information about this SweepstakesEnter Sweepstakes Directly Enter Disney Sweepstakes Disney sweepstakes are so popular that I've created a separate section just for them. So if you'd like to win a trip to Disney for yourself and your family, be sure to visit the Disney Sweepstakes List.