Headingley Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to AU$703 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Your Headingley Holiday

Book a customised Headingley holiday package that includes everything you need and nothing you don't. Great for markets, cycling and cafes, think about basing yourself in the neighbourhood of Downtown Winnipeg. Love to get out and explore? BellMTS Iceplex, Assiniboia Downs and Unicity Mall are just a few of the top places to visit during your trip to Headingley. Your ideal Headingley holiday is just clicks away. Explore hotels, flights and more on Expedia for a getaway that's tailored to suit your style.

Headingley Holiday

Headingley Essential Information

Language
English
Currency
Canadian dollars
Closest Airport
Winnipeg James Armstrong Richardson Intl. Airport (YWG)
Population
3,200
Max Temp Winter
-11.11ºC
Max Temp Summer
24ºC
Top Sights
Assiniboine Park Zoo, Celebrations Dinner Theatre and Burton Cummings Theatre

Our pick of the best Headingley Hotel Deals

Best Western Plus Winnipeg West

Best Western Plus Winnipeg West

2.5 out of 5
4140 Portage Avenue, Headingley, MB
Fully refundableReserve now, pay when you stay
The price is AU$198 per night from 31 Aug to 1 Sept
AU$198
31 Aug - 1 Sept
includes taxes & fees
8.8/10 Excellent! (1,007 reviews)
"Nice, spacious room."

Reviewed on 18 Aug. 2025

Best Western Plus Winnipeg West
Motel 6 Headingley, MB - Winnipeg West

Motel 6 Headingley, MB - Winnipeg West

2 out of 5
4400 Portage Avenue, Hwy 101 North, Headingley, MB
Fully refundableReserve now, pay when you stay
The price is AU$193 per night from 14 Sept to 15 Sept
AU$193
14 Sept - 15 Sept
includes taxes & fees
9/10 Wonderful! (1,134 reviews)
"It was very clean, quiet and the beds were so comfortable! The continental breakfast was lacking in options and availability. The coff and additives were excellent 👍. Overall I am impressed and would recommend this hotel to everyone"

Reviewed on 17 Aug. 2025

Motel 6 Headingley, MB - Winnipeg West
Birchwood Inn, BW Premier Collection

Birchwood Inn, BW Premier Collection

3 out of 5
2520 Portage Ave, Winnipeg, MB
Fully refundableReserve now, pay when you stay
The price is AU$231 per night from 7 Sept to 8 Sept
AU$231
7 Sept - 8 Sept
includes taxes & fees
8.6/10 Excellent! (1,233 reviews)
"Older property but clean and quiet. Easy to get to."

Reviewed on 18 Aug. 2025

Birchwood Inn, BW Premier Collection
See all 478 properties in Headingley
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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Headingley holiday package cost?
You can pick up a holiday package to this top destination on Expedia. However, how much your holiday 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?
If you're hoping to book a cheap Headingley holiday package, consider planning a trip in January, October and November. You'll typically find better rates on airfares and hotels during these quieter months — ideal for budget-conscious travellers.
How many days is enough for Headingley?
We recommend booking a Headingley holiday for a minimum of 2 days. This will allow you enough time to visit top attractions including John Blumberg Softball Complex and John Blumberg Golf Course, as well as check out neighbourhoods like Westdale and Buchanan. You might even be able to fit in a day trip beyond Headingley.
Is it worth booking a holiday package to Headingley?
Headingley is a good holiday destination with attractions like BellMTS Iceplex among the many things to keep you entertained. Whether you're heading away with the family or getting away with friends, a Headingley holiday promises fun 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 travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Headingley holiday as a package?
An Expedia holiday package could land you significant savings when compared to booking accommodation and flights individually. Better still, you can personalise 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 holiday 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.
How to plan a trip to Headingley?

  1. Choose when to get away: Check your calendar and get packing. Your favourite season and the activities available will also help you decide when to holiday in Headingley.
  2. Figure out your budget: Ensure you have enough money to cover everything from transportation and food to activities and airfares. Your hotel will likely be the biggest expense during your trip to Headingley.
  3. Work out your trip length: Think about how long you want to spend exploring Headingley. Plan your days so you can get to all the activities and attractions you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a personalised Headingley holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.