Winter Sweepstakes
Found 27 total
Enter to win the Tourism Whistler Go Bigger in Whistler Winter Trip Contest.
One Grand Prize winner and a guest get a Whistler, BC winter trip for Winter 2027/28: round-trip coach airfare to Vancouver, private SUV transfers to Whistler, six nights at The Westin Resort & Spa Whistler, 3-day Whistler Blackcomb lift tickets and premium ski or snowboard rentals for two, a Dawn Patrol heli-skiing experience, a Whistler sightseeing tour, Squamish Lil'wat Cultural Centre admission plus a $50 gift card, and two dinners (ARV CAD $14,000 / USD $9,838).
Open to residents of the US (excluding NY, FL and PR), Canada (excluding Quebec), Australia and the UK who are the age of majority. Ends May 5, 2027 at 11:59 AM PDT.
To enter, register free on the contest page with your name, email, phone and country for 1 entry; opt in to the Whistler Insider newsletter for 1 bonus entry (max 2). The winner is drawn on or about May 10, 2027, contacted by email or phone, and must answer a skill-testing question.
Win $9,838 in value – Tourism Whistler Go Bigger in Whistler Winter Trip Contest - Enter Now
Enter to win the Oak Island Resort Winter Getaway Giveaway.
One winner gets a free two-night cabin stay at Oak Island Resort Campground in Manitoba, to be used by April 30, 2027.
Ends October 25, 2026 at 11:59 PM CDT.
To enter, like and share the Facebook post and tag a friend you would bring along. The winner will be announced Monday, October 26, 2026.
Win $300 in value – Oak Island Resort Winter Getaway Giveaway - Enter Now
Enter to win the Agave Azul Cocina Mexicana Gift Card Giveaway - 6 Winners.
Six winners each get a $100 Agave Azul gift card, one winner per location: Kirkman, Winter Park, Winter Springs, Windermere, Gateway and Dr. Phillips ($600 total).
Ends Sunday, October 25, 2026 at 11:59 PM EDT.
To enter, follow @agaveazulcocinamex on Instagram, comment your favorite Agave Azul location and tag someone you would bring. One winner will be selected from each location's comments and notified by DM.
Win $600 in value – Agave Azul Cocina Mexicana Gift Card Giveaway - 6 Winners - Enter Now
Enter to win the Upper Deck 2026-27 NHL My MVP Program Contest. There are 33 Winners.
Thirty-three winners: the Ultimate MVP gets two tickets to a 2027 Stanley Cup Playoffs game, their own Upper Deck NHL MVP trading card, $500 by check, luggage, three boxes of Upper Deck NHL cards ($350) and two tickets to the NHL Winter Classic or Stadium Series ($4080 total). Thirty-two Team MVP winners each get a framed trading card with their photo, a hat, a box of cards and a play-mat ($150 each). Total $8880.
To enter, create an account on the contest website and submit 1 to 5 photos of yourself in your favorite NHL team's gear with a short written statement. Limit one entry per person. Nominees are voted on by fans and a panel picks the winners.
Open to legal residents of the 50 US states, DC and Canada who are 18+ and the age of majority. Ends October 23, 2026 at 12:00 PM PDT (voting continues to December 4).
Win $8,880 in value – Upper Deck 2026-27 NHL My MVP Program Contest - 33 Winners - Enter Now
Enter to win the Minute Suites Winter Escape Getaway Giveaway.
One winner receives a $5000 Getaway Your Way package: $1500 toward airfare, $2500 toward a hotel or Airbnb, a $500 Minute Suites credit and a $500 Visa gift card.
To enter, submit the form on the Minute Suites Winter Escape page and reply YES to the confirmation text, or mail in a 3.5 x 5 inch card as described in the official rules. Limit one initial entry per person. Earn one bonus entry for each friend who enters through your referral link, and up to 15 more bonus entries for Minute Suites stays or by free mail-in request.
Open to legal residents of the 50 US states and DC 18+. Ends November 15, 2026 at 11:59 PM CST.
Win $5,000 in value – Minute Suites Winter Escape Getaway Giveaway - Enter Now
Enter to win the Kylie Cosmetics Winter Kissed Collection Sweepstakes - 10 Winners.
Ten winners each receive a Kylie Cosmetics King Kylie PR Set (ARV at least $225 each, $2250 total).
To enter, sign up for the Kylie Cosmetics marketing list (email and phone) on kyliecosmetics.com. Limit one entry per person.
Open to legal residents of the 50 US states and DC 18+. Ends October 31, 2026 at 11:59 PM PDT. Winners are drawn on or about November 30.
Win $2,250 in value – Kylie Cosmetics Winter Kissed Collection Sweepstakes - 10 Winners - Enter Now
Enter to win the Visit Mountaineer Country Convention and Visitors Bureau Winter Cabin Getaway.
This giveaway includes the following prize package.
- Two-night stay at Mountain Creek Cabins, December 4–6
- $100 gift card to Tropics
- $100 gift card to The Lakehouse
- Camping essentials basket from The Lakehouse
Cabins are not ADA accessible. The Number of Winners: 1 ARV: Estimated $1,300 USD total.
Enter to win the Swift Industries x Outdoor Research Weather or Not Riding Giveaway - 2 Winners.
Grand Prize ($2,975): a winter riding kit including a Primos Dame bicycle ($949, winner selects size), a Swift Industries Zeitgeist bike bag and other bags, a $250 Woolly Clothing Co. gift card, Outdoor Research rain jacket and pants, and Portland Design Works fenders, cage, bottle and tools.
Runner-Up Prize ($490): a Swift Industries Capstone handlebar bag, Outdoor Research base layer and gloves, and Portland Design Works accessories.
To enter, submit the entry form on the Swift Industries giveaway page. You may enter only once. No purchase necessary.
Open to US residents 13+. Ends October 22, 2026 at 6:00 PM PDT. Winners are drawn at random and notified by email.
Enter to win the Ski Trip to Golden, BC Giveaway.
One winner and a companion receive a winter ski trip to Golden, British Columbia (approx. CAD $10,000), including up to CAD $2000 round-trip airfare reimbursement to Calgary for two, Champagne Powder Shuttle transfers, Golden–Kicking Horse Connector transport, five nights at Copper Horse Lodge, two days skiing/snowboarding at Kicking Horse Mountain Resort, lunch at Eagle's Eye, one day of CMH Purcell heli-skiing, plus restaurant and retail reimbursements in Golden as stated in the rules.
To enter, complete the Gleam entry on the Tourism Golden trip giveaway page. Optional marketing signup adds bonus entries.
Open to legal residents of Canada (excluding Quebec), the United States (excluding New York, Washington, and Florida), and the United Kingdom, 19+. Ends November 30, 2026 at 11:59 PM Mountain Time.
Win $10,000 in value – Ski Trip to Golden, BC Giveaway - Enter Now
Enter to win the The Meating Place Warm Up Your Winter Giveaway - 5 Winners.
Five winners each receive a $500 gift card to The Meating Place, a butcher shop in Portland, Oregon ($2,500 total).
To enter, fill out the giveaway form with your name, email and phone number (entering adds you to the monthly newsletter). Limit one entry per person.
Open to US residents 18+. The giveaway ends December 26, 2026 at 11:59 PM PST.
Win $2,500 in value – The Meating Place Warm Up Your Winter Giveaway - 5 Winners - Enter Now
