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Parents Canada--Beaches Resort in Jamaica Contest
Enter for a chance to win a family trip for four (2 adults, 2 children under 15) to Beaches Resorts in Jamaica, worth $9,000. The prize includes airfare, seven nights accommodations at an all-inclusive resort.
Restrictions:  18 or older--no QC
End Date: September 30, 2019posted on November 14, 2018
Thanks to: Parallel for telling me about this one
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Espace Pour La Vie--Follow The Monarchs Contest
Enter for a chance to win a trip for four people to Mexico to visit a monarch wintering site, worth $8,800.
Restrictions:  18 or older--QC only
End Date: August 21, 2019posted on April 24, 2019
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MLB Braves--Toyota Stolen Base Challenge Sweepstakes
Enter for a chance to win up to 162 prizes of $50 to $8,100, all depending on when there is a stolen base in the game (see rules). There is also a prize of a $500 Marathon gas card.
Restrictions:  18 or older--no FL, NY or QC--one entry per household.
End Date: September 29, 2019posted on May 5, 2019
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Tourism Vancouver--You Belong In Vancouver Sweepstakes
Enter for a chance to win a trip for two to Vancouver to attend the Queer Film Festival from August 13-23, including airfare, nine nights accommodations and passes, all worth $8,000.
Restrictions:  19 or older in Canada--no QC--21 or older in the US--no FL
End Date: December 31, 2019posted on May 22, 2019
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Nature TTL--Luxury Photo Safari Giveaway
Enter for a chance to win a safari for two in Kenya. It's worth $7,500 and does not include airfare.
Restrictions:  Age of Majority
End Date: July 31, 2019posted on July 13, 2019
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BCAA--Connections Contest
Enter for a chance to win a trip for two to Australia, worth $7,500, awarded as a cheque.
Restrictions:  19 or older--BC only
End Date: September 30, 2019posted on April 23, 2019
Thanks to: Astrid for telling me about this one
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Simons--Quebec City Getaway Contest
Enter for a chance to win a trip for two to Quebec city worth $7,460. The rules say you have to be a member of the Simons loyalty program. If you aren't, it's free to join and you can sign up here.
Restrictions:  18 or older
End Date: July 31, 2019posted on July 2, 2019
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Tourisme Outaouais--Outfitters Fishing Trip Contest
Enter for a chance to win a Princecraft boat with a 9.9hp a Mercury engine, a trailer and a fishing trip, all worth $7,000.
End Date: November 30, 2019posted on May 29, 2019
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Equine Connection--$6,400 Horse Welfare Giveaway
Enter for a chance to win $6,400 in horse related courses and products. Newsletter sign-up is required.
Restrictions:  18 or older
End Date: August 30, 2019posted on July 6, 2019
Thanks to: Parallel for telling me about this one
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Tourism Whistler--Adventure Differently In Whistler Contest
Enter for a chance to win a trip for two to Whistler, BC, worth $6,337. The prize includes airfare, six nights accommodations, various activities and restaurant gift certificates.
Restrictions:  Age of Majority--no QC, FL, or NY--also open to Australia and the UK
End Date: September 26, 2019posted on June 8, 2019
Thanks to: Parallel for telling me about this one
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