Headingley Vacations from $784

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Your Headingley Vacation

When a getaway to the city is calling, answer it with a vacation package to Headingley. The neighborhood of Downtown Winnipeg, which is great for markets, cafes and bars and pubs, makes a fantastic base for your adventures. Fill your itinerary with visits to Assiniboia Downs, BellMTS Iceplex and Unicity Mall, some of the attractions you just have to see during a trip to Headingley. Don't delay visiting this city any longer. The perfect Headingley vacation is a couple of clicks away with Expedia.

The Latest Headingley vacation packages

Price found within the past 48 hours. Click for updated prices.
Canad Inns Destination Centre Garden City

Canad Inns Destination Centre Garden City

3 out of 5
Leila-McPhillips Triangle
Price was $879, price is now $784 per person
$784
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Winnipeg (YWG)
8.2/10 Very Good! (1,012 reviews)
I was quite disappointed with this particular experience, as CanadInns hotels in Wpg are usually held to a certain standard. Firstly, the room (a Deluxe Queen 2 beds) looked far different than the picture; much smaller, amenities in the room were essentially useless; hardly any of the power outlets worked, save for maybe 3, which were already being used for the TV, lamps, and microwave. The room was advertised as soundproof, most definitely was not. Outdated appliances on the room, no where to rest aside from the bed

Reviewed on Oct 25, 2026

Humphry Inn & Suites

Humphry Inn & Suites

2.5 out of 5
Downtown Winnipeg
Price was $941, price is now $833 per person
$833
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Winnipeg (YWG)
8.4/10 Very Good! (1,756 reviews)
Only complaint would be breakfast

Reviewed on Oct 27, 2026

Canad Inns Destination Centre Transcona

Canad Inns Destination Centre Transcona

3 out of 5
Transcona
Price was $884, price is now $787 per person
$787
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Winnipeg (YWG)
8.4/10 Very Good! (1,004 reviews)

Canad Inns Destination Centre Windsor Park

Canad Inns Destination Centre Windsor Park

3 out of 5
Windsor Park
Price was $875, price is now $785 per person
$785
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Winnipeg (YWG)
8/10 Very Good! (1,004 reviews)

The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel

The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel

4 out of 5
Downtown Winnipeg
Price was $967, price is now $888 per person
$888
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Winnipeg (YWG)
9.2/10 Wonderful! (1,362 reviews)

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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

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
$96 nightly
The price is $108 total per night from Nov 11 to Nov 12
$108 total
Nov 11 - Nov 12
Total with taxes and fees
9.2/10 Wonderful! (1,702 reviews)
"i"

Reviewed on Oct 27, 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
$133 nightly
The price is $149 total per night from Nov 15 to Nov 16
$149 total
Nov 15 - Nov 16
Total with taxes and fees
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
$102 nightly
The price is $121 total per night from Nov 9 to Nov 10
$121 total
Nov 9 - Nov 10
Total with taxes and fees
Victoria Inn Hotel and Convention Centre Winnipeg
See all 703 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.

Find the Best Headingley Vacation Packages

Headingley Essential Information

Language
English
Currency
Canadian dollars
Closest Airport
Winnipeg James Armstrong Richardson Intl. Airport (YWG)
Population
3,200
Max Temp Winter
12ºF
Max Temp Summer
75ºF
Top Sights
Assiniboine Park Zoo, Celebrations Dinner Theatre and Burton Cummings Theatre

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Frequently asked questions

How much does a Headingley vacation package cost?
You can pick up a vacation package to this top destination from $784 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?
You can typically find lower prices and greater availability in November, December and January. Take a look at our cheap Headingley vacation packages and you could land some great off-season discounts.
How many days is enough for Headingley?
Headingley vacations come in all shapes and sizes, but to get a true feel for this destination, we'd say 2 days is about right. This will mean you can fit in top sights like John Blumberg Softball Complex and John Blumberg Golf Course and track down some hidden gems. Don't forget to visit neighborhoods such as Westdale and Buchanan either. If you're clever with your time, you can even allow for a day trip or two from Headingley too.
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 busy. Whether you're heading away with the family or planning a trip with friends, a Headingley vacation promises a good time 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.
Does Expedia offer Book Now, Pay Later Headingley vacation packages?
If you're anything like us, you love exploring new places but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the overall cost of your Headingley break across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.