Headingley Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$2,400 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

Headingley Holiday

Our pick of the best Headingley Hotel Deals

Motel 6 Headingley, MB - Winnipeg West

Motel 6 Headingley, MB - Winnipeg West

2 out of 5
4400 Portage Avenue Headingley MB
Fully refundableReserve now, pay when you stay
The price is NZ$164 per night from 22 Nov to 23 Nov
NZ$164
22 Nov - 23 Nov
includes taxes & fees
9.2/10 Wonderful! (1,718 reviews)
"Very nice room. Had a full size fridge and a cook top. We were able to stay in our room with take out and heat up once our food was cold. Only complaint I would have is you can hear the people above you walking. I would try to stay on the second floor next time but definitely would be back. Staff ..."

Reviewed on 4 Nov 2026

Motel 6 Headingley, MB - Winnipeg West
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 NZ$280 per night from 8 Nov to 9 Nov
NZ$280
8 Nov - 9 Nov
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
"Just an excellent hotel. Clean spacious rooms. Fantastic breakfast"

Reviewed on 1 Nov 2026

Best Western Plus 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
The price is NZ$206 per night from 6 Dec to 7 Dec
NZ$206
6 Dec - 7 Dec
includes taxes & fees
Victoria Inn Hotel and Convention Centre Winnipeg
See all 694 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.

Stay near popular Headingley attractions

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.
See properties

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.