Headingley Vacations from $688
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Your Headingley Vacation
When a getaway to the city is calling, answer it with a vacation package to Headingley. The neighborhood of Downtown Winnipeg, which is great for markets, cafes and bars and pubs, makes a fantastic base for your adventures. Fill your itinerary with visits to Assiniboia Downs, BellMTS Iceplex and Unicity Mall, some of the attractions you just have to see during a trip to Headingley. Don't delay visiting this city any longer. The perfect Headingley vacation is a couple of clicks away with Expedia.
The Latest Headingley vacation packages
Price found within the past 48 hours. Click for updated prices.
Wyndham Garden Winnipeg Airport
St. James
Price was $991, price is now $860 per person
$860
per person
Aug 16 - Aug 22
found 10 hours ago
Roundtrip non-stop flight included
San Francisco (SFO) to Winnipeg (YWG)
8.6/10 Excellent! (675 reviews)
What a nightmare from the beginning….Couldn’t enter the lobby - was locked. Another guest tried to let me in, the card couldn’t the door.
You can’t use the elevator without swiping a card first…
But the best part is the damage deposit, 250! They can’t refund it unless you’re physically there! I have never hear of this, I don’t live there and they kept telling me I have to go back for a deposit, from a credit card???? now they can’t do anything.. after a could days and a nightmare of call experiences, the best they can do is they claim to “send me a cheque” which is nuts… never had this issue before, stay away from this place or you will never get your security deposit back from this prison!
Reviewed on Jul 13, 2026
Sandman Hotel & Suites Winnipeg Airport
St. James
Price was $960, price is now $841 per person
$841
per person
Sep 15 - Sep 19
found 5 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Winnipeg (YWG)
8.2/10 Very Good! (1,739 reviews)
Dirty swimming pool, dirty carpet, some part dirty towels.
Reviewed on Jul 14, 2026
Travelodge by Wyndham Winnipeg East
St. Vital
Price was $879, price is now $775 per person
$775
per person
Aug 16 - Aug 22
found 10 hours ago
Roundtrip non-stop flight included
San Francisco (SFO) to Winnipeg (YWG)
8.2/10 Very Good! (1,797 reviews)
The place is looking rundown. Room was not cleaned well. Hallway carpet is not clean. Otherwise ok stay
Reviewed on Jul 14, 2026
Stay near popular Headingley attractions
Headingley Hotel Deals
Best Western Plus Winnipeg West
4140 Portage Avenue Headingley MB
Fully refundableReserve now, pay when you stay
$131 nightly
The price is $147 total per night from Jul 26 to Jul 27
$147 total
Jul 26 - Jul 27
Total with taxes and fees
9/10 Wonderful! (1,017 reviews)
"The whole third floor including my room smelled terrible. Like too many sweaty people in a stuffy, humid environment. For the $270/night I paid, I would have hoped for a nicer stay. The bathrooms are very dated and could be cleaner. There are next to no plug ins available for charging, and nowhere ..."
Reviewed on Jul 14, 2026
Motel 6 Headingley, MB - Winnipeg West
4400 Portage Avenue Headingley MB
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $137 total per night from Jul 19 to Jul 20
$137 total
Jul 19 - Jul 20
Total with taxes and fees
9.2/10 Wonderful! (1,579 reviews)
"The room was neat and clean. The mini fridge was loud, but I was able to unplug it to sleep. Great coffee, muffins, and fresh fruit available on the way out in the morning. One small gripe is that the location is a bit of a pain if you’re travelling West as you can’t make a direct turn south into ..."
Reviewed on Jul 14, 2026
Victoria Inn Hotel and Convention Centre Winnipeg
1808 Wellington Ave Winnipeg MB
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $141 total per night from Aug 5 to Aug 6
$141 total
Aug 5 - Aug 6
Total with taxes and fees
8.4/10 Very Good! (3,135 reviews)
"Me and my sister-in-law stayed with my four-year-old nephew and 4-month-old nephew. The pool was awesome for the kids and my sister-in-law and I were very happy with our stay"
Reviewed on Jul 14, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Find the Best Headingley Vacation Packages
Headingley Essential Information
Language | English |
|---|---|
Currency | Canadian dollars |
Closest Airport | Winnipeg James Armstrong Richardson Intl. Airport (YWG) |
Population | 3,200 |
Max Temp Winter | 12ºF |
Max Temp Summer | 75ºF |
Top Sights | Assiniboine Park Zoo, Celebrations Dinner Theatre and Burton Cummings Theatre |
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Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
