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Air Transat--Toast To Travel Contest
Enter for a chance to win a round-trip flight for four people to the Air Transat destination of your choice. It's worth up to $6,000.
Restrictions:  Age of Majority
End Date: July 30, 2019posted on June 30, 2019
Thanks to: kadubb for telling me about this one
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Tripco Travel--AMAWaterways River Cruise Contest
Enter for a chance to win a European river cruise for two including airfare to Paris or Amsterdam.
End Date: December 9, 2019posted on April 2, 2019
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Honda--Win a Bike Contest
Enter for a chance to win a 2019 Honda motorcycle and a $300 dealer accessories credit, all worth $5,799.
Restrictions:  Age of Majority
End Date: December 31, 2019posted on January 30, 2019
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Men's Health--Austin Experience Sweepstakes
Enter for a chance to win a fitness-themed trip for two to Austin, Texas, worth $5,500. The prize includes airfare, two nights accommodations, some meals, bat-watching sunset cruise, private training session and more. Make sure you select the "no free trial" link unless you want a subscription.
Restrictions:  18 or older--no QC
End Date: August 12, 2019posted on June 30, 2019
Thanks to: SandiT for telling me about this one
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Voyages Gendron--Casa de Campo Contest
Enter for a chance to win a $5,500 golf trip for two people to the Dominican Republic. The flight is from Montreal and the entry for is in French but the contest is open to all of Canada.
Restrictions:  25 or older
End Date: September 8, 2019posted on April 29, 2019
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Northern Saunas--Clearlight Sanctuary 2 Sweepstakes
Enter for a chance to win a Clearlight Sanctuary 2 infrared sauna worth $5,299. Newsletter sign-up is required.
Restrictions:  18 or older--no AK, HI or QC
End Date: September 2, 2019posted on July 4, 2019
Thanks to: NorthernSaunas/Parallel for telling me about this one
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Intrepid Travel--Mind Body Spirit Sweepstakes
Enter for a chance to win two spots on Intrepid Travel's India: Mind, Body, Spirit trip with a flight credit up to $2,000 and a $250 Lucky Brand gift card. It's worth $5,000.
Restrictions:  18 or older--no AK, HI, MI or RI
End Date: August 1, 2019posted on July 18, 2019
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Air Miles--Vancouver with Said the Whale Contest
Enter for a chance to win a $5,000 trip for two to Vancouver for a yacht experience with Said the Whale on September 5.
Restrictions:  Age of Majority--you must be an Air Miles collector
End Date: August 1, 2019posted on July 11, 2019
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Sensible Portions--Cash Giveaway (Facebook)
Enter for a chance to win $5,000.
End Date: August 2, 2019posted on July 10, 2019
Thanks to: Parallel for telling me about this one
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Expedia Cruise Ship Centres--Dream Vacation Sweepstakes.
Enter for a chance to win a 7-night Caribbean cruise for two, worth $5,000.
Restrictions:  21 or older
End Date: November 5, 2019posted on July 9, 2019
Thanks to: Parallel for telling me about this one
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