Headingley Vacations from $720

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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 Transcona

Canad Inns Destination Centre Transcona

3 out of 5
Transcona
Price was $824, price is now $720 per person
$720
per person
Dec 20 - Dec 23
found 21 hours ago
Roundtrip non-stop flight included
Billings (BIL) to Winnipeg (YWG)
8.2/10 Very Good! (1,015 reviews)
The staff were wonderful. Helpful and efficient. The room was awful. Old, dingy, small and noisy.

Reviewed on Oct 25, 2025

Canad Inns Destination Centre Fort Garry

Canad Inns Destination Centre Fort Garry

3 out of 5
Fort Garry
Price was $842, price is now $730 per person
$730
per person
Dec 20 - Dec 23
found 21 hours ago
Roundtrip non-stop flight included
Billings (BIL) to Winnipeg (YWG)
8/10 Very Good! (1,086 reviews)
The first night we were there,the room was dated. We had loud neighbors that night and we requested to be moved to a "renovated" room for the second night. Staff apologized for our experience, moved us to a much nicer room and refunded one nights stay. They dealt with the issue quickly and fairly I thought.

Reviewed on Oct 22, 2025

Humphry Inn & Suites

Humphry Inn & Suites

2.5 out of 5
Downtown Winnipeg
Price was $885, price is now $774 per person
$774
per person
Dec 20 - Dec 23
found 21 hours ago
Roundtrip non-stop flight included
Billings (BIL) to Winnipeg (YWG)
8.2/10 Very Good! (1,415 reviews)
Noisy, no regular TV

Reviewed on Oct 24, 2025

Canad Inns Destination Centre Polo Park

Canad Inns Destination Centre Polo Park

3 out of 5
Polo Park
Price was $864, price is now $764 per person
$764
per person
Dec 20 - Dec 23
found 21 hours ago
Roundtrip non-stop flight included
Billings (BIL) to Winnipeg (YWG)
7.8/10 Good! (1,004 reviews)
Great staff, great location. We had a wonderful stay.

Reviewed on Oct 15, 2025

The Fairmont Winnipeg Gold Experience

The Fairmont Winnipeg Gold Experience

4 out of 5
Exchange District
Price was $1,167, price is now $1,035 per person
$1,035
per person
Dec 20 - Dec 23
found 21 hours ago
Roundtrip non-stop flight included
Billings (BIL) to Winnipeg (YWG)
8.4/10 Very Good! (27 reviews)
Enjoyed the Fairmont Gold Experience. Gold Lounge was closed for renovations on our last day, but the hotel took great care of us in the restaurant for breakfast. We will be back.

Reviewed on Feb 5, 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
$118 nightly
The price is $132 total per night from Nov 10 to Nov 11
$132 total
Nov 10 - Nov 11
Total with taxes and fees
8.8/10 Excellent! (1,012 reviews)
Good clean place to stay, close to park and ride. Didn’t appreciate the call at 11:01 telling is to leave while already walking out the door.

Reviewed on Oct 18, 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 refundable
$73 nightly
The price is $82 total per night from Nov 2 to Nov 3
$82 total
Nov 2 - Nov 3
Total with taxes and fees
9/10 Wonderful! (1,181 reviews)
No decaf coffee or tea. Otherwise fine.

Reviewed on Oct 23, 2025

Motel 6 Headingley, MB - 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
$237 nightly
The price is $281 total per night from Nov 2 to Nov 3
$281 total
Nov 2 - Nov 3
Total with taxes and fees
8.4/10 Very Good! (2,385 reviews)
Rooms were spacious and good price. The pool area is great for kids we had a blast

Reviewed on Oct 20, 2025

Victoria Inn Hotel and Convention Centre Winnipeg
See all 504 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 $720 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.