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Travel + Leisure--World's Best Awards Giveaway
Enter for a chance to win one of five prizes of a trip including one prizes of a world cruise worth $199,990.
Restrictions:  18 or older
End Date: January 2, 2020posted on November 13, 2019
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Orvis--Barbour Range Rover 125 Year Anniversary Sweepstakes
Enter for a chance to win a restored 1995 Range Rover County worth $125,000.
Restrictions:  18 or older--no RI
End Date: March 31, 2020posted on October 2, 2019
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Vacation Myrtle Beach--Great Myrtle Beach Condo Giveaway
Enter for a chance to win an oceanfront Myrtle Beach condo valued at nearly $100,000 or you can take $50,000 cash instead. You can enter this one at eight different websites for a total of eight entries - see the rules for the other entry locations.
Restrictions:  21 or older
End Date: March 31, 2020posted on April 11, 2019
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Pineapple Express Wellness--Launch Sweepstakes
Enter for a chance to win $100,000. This one is open to California only.
Restrictions:  18 or older--CA only
End Date: December 31, 2019posted on April 6, 2019
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Ford--Hall Of Fans Sweepstakes
Enter for a chance to win a trip for two to Miami with ticket to the Super Bowl and a 2019 Ford F-150 pickup truck, all worth $64,085.
Restrictions:  18 or older
End Date: January 27, 2020posted on July 29, 2019
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Exodus Travels--Life Of Adventure Sweepstakes
Enter for a chance to win a $2,500 travel credit each year for 25 years. It's worth $62,500.
Restrictions:  21 or older--no NY or QC
End Date: February 17, 2020posted on November 13, 2019
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Mobil 1 Hot--Wheels Legends Sweepstakes
Enter for a chance to win a Chevrolet Camaro with $15,000 cash - worth $60,000.
Restrictions:  18 or older
End Date: November 22, 2019posted on March 21, 2019
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Bluegreen Vacations--Passport To Adventure Sweepstakes
Enter for a chance to win $55,500. Note that this company sells time-share vacation properties and they will call you if you agree to receive calls. There's a button on the entry form that tells them not to call or text and you still get an entry into the sweepstakes.
Restrictions:  21 or older--no ID, ND or SD
End Date: May 1, 2020posted on May 5, 2019
Thanks to: FJB for telling me about this one
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Ixia--$50k Network Makeover Sweepstakes
Enter for a chance to win a $50,000 network makeover and other networking gear.There are also 50 prizes of Ixia-branded swag, worth $200. The entry form requires tech-company information. You can read the rules here.
Restrictions:  18 and older--no QC, AZ, FL, NY or RI--also open to other countries (see rules)
End Date: December 1, 2019posted on November 13, 2019
Thanks to: cabn44 for telling me about this one
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RumbleOn--Harley-Davidson Motorcycle Sweepstakes
Enter for a chance to win a Harley-Davidson motorcycle, worth $50,000.
Restrictions:  18 or older--no AK, HI, NY or RI
End Date: December 1, 2019posted on May 20, 2019
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