Headingley Holidays

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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 27 July to 28 July
AU$198
27 July - 28 July
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
"Great room and location."

Reviewed on 9 Jul. 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$205 per night from 21 July to 22 July
AU$205
21 July - 22 July
includes taxes & fees
9/10 Wonderful! (1,117 reviews)
"Spacious room with everything needed to cook."

Reviewed on 9 Jul. 2025

Motel 6 Headingley, MB - Winnipeg West
Victoria Inn Hotel and Convention Centre Winnipeg
Victoria Inn Hotel and Convention Centre Winnipeg
3 out of 5
1808 Wellington Ave, Winnipeg, MB
Fully refundableReserve now, pay when you stay
8.4/10 Very Good! (2,097 reviews)
"Nice stay"

Reviewed on 9 Jul. 2025

Get rates
Victoria Inn Hotel and Convention Centre Winnipeg
See all 518 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.