Headingley Vacations from $1,197

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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 $1,255, price is now $1,197 per person
$1,197
per person
Dec 1 - Dec 4
found 24 hours ago
Roundtrip flight included
Augusta (AGS) to Winnipeg (YWG)
8/10 Very Good! (1,008 reviews)
I did not enjoy the over wellemin

Reviewed on Sep 19, 2025

Humphry Inn & Suites

Humphry Inn & Suites

2.5 out of 5
Downtown Winnipeg
Price was $1,339, price is now $1,253 per person
$1,253
per person
Dec 1 - Dec 4
found 24 hours ago
Roundtrip flight included
Augusta (AGS) to Winnipeg (YWG)
8.2/10 Very Good! (1,374 reviews)
All good thx for everything

Reviewed on Sep 21, 2025

Victoria Inn Hotel and Convention Centre Winnipeg

Victoria Inn Hotel and Convention Centre Winnipeg

3 out of 5
St. James
Price was $1,489, price is now $1,394 per person
$1,394
per person
Dec 1 - Dec 4
found 24 hours ago
Roundtrip flight included
Augusta (AGS) to Winnipeg (YWG)
8.4/10 Very Good! (2,296 reviews)
Newly renovated. Much nicer than I expected.

Reviewed on Sep 22, 2025

Canad Inns Destination Centre Fort Garry

Canad Inns Destination Centre Fort Garry

3 out of 5
Fort Garry
Price was $1,316, price is now $1,241 per person
$1,241
per person
Dec 1 - Dec 4
found 24 hours ago
Roundtrip flight included
Augusta (AGS) to Winnipeg (YWG)
8/10 Very Good! (1,074 reviews)
Good rooms,good restaurant

Reviewed on Sep 6, 2025

Canad Inns Destination Centre Polo Park

Canad Inns Destination Centre Polo Park

3 out of 5
Polo Park
Price was $1,288, price is now $1,221 per person
$1,221
per person
Dec 1 - Dec 4
found 24 hours ago
Roundtrip flight included
Augusta (AGS) to Winnipeg (YWG)
7.8/10 Good! (1,009 reviews)
It was close to shopping and restaurants.

Reviewed on Sep 22, 2025

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Discover the most popular places to visit in Headingley

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

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
$115 nightly
The price is $129 total per night from Oct 6 to Oct 7
$129 total
Oct 6 - Oct 7
Total with taxes and fees
8.8/10 Excellent! (1,016 reviews)
Exclent
"It was excellent stay clean quite and good staff"

Reviewed on Sep 14, 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
$111 nightly
The price is $125 total per night from Sep 30 to Oct 1
$125 total
Sep 30 - Oct 1
Total with taxes and fees
9/10 Wonderful! (1,140 reviews)
"Not easily exited onto Portage. There’s no left turn allowed. Hallway noise and highway noise were both factors. Rooms are loud as there’s no pictures or carpet. That being said the flooring in the rooms is great and clean. The coffee available is fantastic!"

Reviewed on Sep 14, 2025

Motel 6 Headingley, MB - Winnipeg West
Humphry Inn & Suites

Humphry Inn & Suites

2.5 out of 5
260 Main Street, Winnipeg, MB
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $130 total per night from Sep 28 to Sep 29
$130 total
Sep 28 - Sep 29
Total with taxes and fees
8.2/10 Very Good! (1,388 reviews)
"Friendly staff"

Reviewed on Sep 19, 2025

Humphry Inn & Suites
See all 501 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.

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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 $1,197 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.