Headingley Vacations from $564

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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 $630, price is now $564 per person
$564
per person
Jan 5 - Jan 9
found 13 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Winnipeg (YWG)
16.8/10 Exceptional! (1,005 reviews)
Our room was great, clean, beds were comfortable. Pillows were comfortable. Hot tub was nice and hot. Bathroom was very small but nice. Will stay again.

Reviewed on Nov 15, 2025

Humphry Inn & Suites

Humphry Inn & Suites

2.5 out of 5
Downtown Winnipeg
Price was $749, price is now $622 per person
$622
per person
Jan 5 - Jan 9
found 13 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Winnipeg (YWG)
16.8/10 Exceptional! (1,475 reviews)
The rooms are outdated. The beds are very uncomfortable, the springs in the mattress are easily felt. The window in our room was broken. I was unaware I had to pay to park in the hotel parking lot.

Reviewed on Nov 13, 2025

Canad Inns Destination Centre Polo Park

Canad Inns Destination Centre Polo Park

3 out of 5
Polo Park
Price was $682, price is now $580 per person
$580
per person
Jan 5 - Jan 9
found 13 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Winnipeg (YWG)
15.6/10 Exceptional! (1,006 reviews)
Good staff ...clean room .. Great price and location

Reviewed on Nov 4, 2025

Sandman Signature Winnipeg Airport Hotel & Suites

Sandman Signature Winnipeg Airport Hotel & Suites

4 out of 5
St. James
Price was $748, price is now $665 per person
$665
per person
Jan 5 - Jan 9
found 13 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Winnipeg (YWG)
18/10 Exceptional! (187 reviews)
Everything went well. Staff was very nice

Reviewed on Nov 15, 2025

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 $734, price is now $658 per person
$658
per person
Jan 5 - Jan 9
found 13 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Winnipeg (YWG)
18.4/10 Exceptional! (1,008 reviews)
The first morning I was there for breakfast with a tour group and actually after waiting 20 minutes had to ask for coffee. I did not get any refill as I never saw the waiter again and he did not come to my table to ask about refilling.After tasting the coffee I realized I probably didn’t want to refill. The coffee leave something to be desired Otherwise the food was OK and the hotel was beautiful.

Reviewed on Nov 16, 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

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
$73 nightly
The price is $81 total per night from Nov 23 to Nov 24
$81 total
Nov 23 - Nov 24
Total with taxes and fees
9/10 Wonderful! (1,204 reviews)
Excellent everything

Reviewed on Nov 11, 2025

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
$123 nightly
The price is $138 total per night from Nov 30 to Dec 1
$138 total
Nov 30 - Dec 1
Total with taxes and fees
8.8/10 Excellent! (1,003 reviews)
No thanks

Reviewed on Nov 11, 2025

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
$85 nightly
The price is $101 total per night from Dec 14 to Dec 15
$101 total
Dec 14 - Dec 15
Total with taxes and fees
8.4/10 Very Good! (2,449 reviews)
It was a cozy stay

Reviewed on Nov 12, 2025

Victoria Inn Hotel and Convention Centre Winnipeg
See all 515 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 $564 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.