Headingley Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Headingley

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 3.025.478 ₫ per night from 26 Aug to 27 Aug
3.025.478 ₫
3.388.535 ₫ total
26 Aug - 27 Aug
includes taxes & fees
8.8/10 Excellent! (1,008 reviews)
"Pool is"

Reviewed on 10 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 3.045.465 ₫ per night from 20 Aug to 21 Aug
3.045.465 ₫
3.410.920 ₫ total
20 Aug - 21 Aug
includes taxes & fees
9/10 Wonderful! (1,130 reviews)
"Check in was quick, plenty of parking space. Quiet room with eating area, mini fridge. Room is compact but for a stay on the go it was perfect"

Reviewed on 8 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 3.340.513 ₫ per night from 7 Sept to 8 Sept
3.340.513 ₫
3.951.828 ₫ total
7 Sept - 8 Sept
includes taxes & fees
8.6/10 Excellent! (1,227 reviews)
"Hotel lobby is nice, staff is friendly and efficient, parking lot is a bit dirty and it was highly recommended to use under ground parking, room was clean but there is a bit of a smell"

Reviewed on 8 Aug 2025

Birchwood Inn, BW Premier Collection
See all 520 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.

Popular places to visit

John Blumberg Softball Complex

Catch an event at John Blumberg Softball Complex during your trip to Headingley. Stroll along the riverfront or attend a sporting event in the area.

John Blumberg Softball Complex

Thunder Rapids Fun Park

Bring your family to Thunder Rapids Fun Park and enjoy this exciting theme park in Headingley. Stroll along the riverfront or attend a sporting event in the area.

Thunder Rapids Fun Park

John Blumberg Golf Course

Enjoy a round of golf in Headingley at John Blumberg Golf Course. Experience the area's fascinating museums or attend a sporting event.

John Blumberg Golf Course

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.