Headingley Vacations from ￥178,640

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The Latest Headingley Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Lakeview Inns & Suites - Brandon

Lakeview Inns & Suites - Brandon

2.5 out of 5
per person
Sep 20 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Winnipeg (YWG)
8.8/10 Excellent! (1,169 reviews)
Was great ivs stayed here many times during travel. Thanks for another great stay

Reviewed on Aug 3, 2025

Find the Best Headingley Vacation Packages

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 ￥16,955 per night from Aug 18 to Aug 19
￥16,955
￥18,990 total
Aug 18 - Aug 19
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"Comfy bed and pillows"

Reviewed on Jul 31, 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 ￥16,533 per night from Aug 27 to Aug 28
￥16,533
￥18,518 total
Aug 27 - Aug 28
includes taxes & fees
9/10 Wonderful! (1,126 reviews)
"Excellent pet-friendly option on our way to Ottawa from Calgary. And with easy access to green space -- including a little fenced dog park for the four-legged. Four paws up!"

Reviewed on Jul 29, 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 ￥19,245 per night from Aug 6 to Aug 7
￥19,245
￥22,767 total
Aug 6 - Aug 7
includes taxes & fees
8.6/10 Excellent! (1,222 reviews)
"Beds were comfortable which always makes me happy. Hotel was very clean, staff and amenities were great."

Reviewed on Aug 1, 2025

Birchwood Inn, BW Premier Collection
See all 511 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.

Frequently asked questions

How much does a Headingley vacation package cost?
You can pick up a vacation package to this top destination from ￥178,640 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?
If you're hoping to book a cheap Headingley vacation 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 travelers.
How many days is enough for Headingley?
We recommend booking a Headingley vacation 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 neighborhoods like Westdale and Buchanan. You might even be able to fit in a day trip beyond Headingley.
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 entertained. Whether you're heading away with the family or getting away with friends, a Headingley vacation 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 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.
How to plan a trip to Headingley?

  1. Choose when to get away: Check your calendar and get packing. Your favorite season and the activities available will also help you decide when to vacation 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 personalized Headingley vacation package.

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