Headingley Vacations from $396
Book a Hotel + Flight or Car together to unlock savings
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.
Canad Inns Destination Centre Fort Garry
Fort Garry
$396
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) to Winnipeg (YWG)
8/10 Very Good! (1,432 reviews)
Older hotel but well looked after. Windows in our room 260 needed changing as seal gone and not all sound proof. Our room beside back stairway so heard comings and goings easily.
Restaurant vey good. Food excellent and service was as well
Reviewed on Sep 13, 2026
Norwood Hotel
Norwood East
$428
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) to Winnipeg (YWG)
8.4/10 Very Good! (1,001 reviews)
It looks outdated outside but inside it is newly renovated with a modern style. Improve a little bit of the pressure of the shower. Overall, it is a good location and a good 20 mins walk to The fork Market and 15 mins to the downtown. Parking is not free but affordable. Definitely , I’ll go back here in this hotel. Reese is great and other employees.
Reviewed on Sep 13, 2026
Stay near popular Headingley attractions
John Blumberg Golf Course
8.4/10 (12 reviews)
This 27-hole golf haven features rolling fairways and strategic water hazards along the Assiniboine River. Enjoy both the challenging Emerald Course and more accessible Gold Course.
John Blumberg Softball Complex
8.0/10 (13 reviews)
This premier softball venue has hosted the Pan American Games with its seven immaculate diamonds. Catch the excitement of national tournaments while enjoying refreshments from the sports bar and concession stand.
Headingley Hotel Deals
Motel 6 Headingley, MB - Winnipeg West
4400 Portage Avenue Headingley MB
Fully refundableReserve now, pay when you stay
$100 nightly
$111 total
Oct 5 - Oct 6
Total with taxes and fees
9.2/10 Wonderful! (1,639 reviews)
"Staff was super nice and hotel was very clean and put together"
Reviewed on Sep 13, 2026
Best Western Plus Winnipeg West
4140 Portage Avenue Headingley MB
Fully refundableReserve now, pay when you stay
$135 nightly
$151 total
Sep 16 - Sep 17
Total with taxes and fees
Victoria Inn Hotel and Convention Centre Winnipeg
1808 Wellington Ave Winnipeg MB
$111 nightly
$131 total
Sep 30 - Oct 1
Total with taxes and fees
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
How much does a Headingley vacation package cost?
You can pick up a vacation package to this top destination from $396 on Expedia. However, how much your vacation to Headingley costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Headingley?
You can typically find lower prices and greater availability in November, December and January. Take a look at our cheap Headingley vacation packages and you could land some great off-season discounts.
How many days is enough for Headingley?
Headingley vacations come in all shapes and sizes, but to get a true feel for this destination, we'd say 2 days is about right. This will mean you can fit in top sights like John Blumberg Softball Complex and John Blumberg Golf Course and track down some hidden gems. Don't forget to visit neighborhoods such as Westdale and Buchanan either. If you're clever with your time, you can even allow for a day trip or two from Headingley too.
Is it worth booking a vacation package to Headingley?
Headingley is a good vacation destination with attractions like BellMTS Iceplex among the many things to keep you busy. Whether you're heading away with the family or planning a trip with friends, a Headingley vacation promises a good time for everyone.
How to find the best Headingley package deals?
Landing a cheap Headingley package deal is easy with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget, apply some filters and see what's available. You can tweak your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Headingley package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are usually lower.
Is it cheaper to book a Headingley vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking accommodations and flights individually. Better still, you can personalize your Headingley escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Headingley?
Score amazing discounts by reserving your flights in advance with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Headingley escape.
Does Expedia offer Book Now, Pay Later Headingley vacation packages?
If you're anything like us, you love exploring new places but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the overall cost of your Headingley break across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.