Headingley Vacations from $858

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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 Windsor Park

Canad Inns Destination Centre Windsor Park

3 out of 5
Windsor Park
per person
Aug 16 - Aug 21
found 20 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Winnipeg (YWG)
7.6/10 Good! (925 reviews)
Good affordable hotel, little pool with a fun water slide and hot tub which we loved and 2 bars attached as well which is convenient. A bit of sketchy characters due to it being directly beside a club but there was no real trouble, overall quite enjoyed our stay!

Reviewed on Jun 25, 2025

Canad Inns Destination Centre Club Regent Casino Hotel

Canad Inns Destination Centre Club Regent Casino Hotel

3 out of 5
Transcona
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Winnipeg (YWG)
9/10 Wonderful! (1,200 reviews)
casino sucked, didn’t win any money😂

Reviewed on Jun 29, 2025

Country Inn & Suites by Radisson, Winnipeg, MB

Country Inn & Suites by Radisson, Winnipeg, MB

2.5 out of 5
St. James
per person
Aug 16 - Aug 21
found 20 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Winnipeg (YWG)
7.6/10 Good! (1,000 reviews)
We checked in early thanks to staff. We took the elevator up and all you could smell was pot. We went out shortly after and came back about 6. No pot smell but noise from kids and parents all good. We went to bed early. Reasonable noise. Got u at 4 to head home and grabbed coffee to go out for a smoke. Got in the elevator only to find out the main floor button was taken out so the delay went down but couldn’t get out? I was panicked but pressed 3rd floor button and it took me u and let me out. I went back in to have a shower and no matter how long I ran it couldn’t get hot water? The staff were friendly unfortunately they couldn’t have done more than they did and were great but I suggest that it is advertised for a room that you advise there are evacuees staying there please? We would have known how over worked staff was and how much damage and noise to expecy

Reviewed on Jun 27, 2025

Canad Inns Destination Centre Transcona

Canad Inns Destination Centre Transcona

3 out of 5
Transcona
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Winnipeg (YWG)
8/10 Very Good! (1,007 reviews)
This is a good place to stay at. It’s clean, safe and family friendly. They have a Giant Tiger close by, in case you ran out of something or need to get some snacks. There’s a mall close by and the casino is just down the street. I like staying at this location.

Reviewed on Jun 23, 2025

Humphry Inn & Suites

Humphry Inn & Suites

2.5 out of 5
Downtown Winnipeg
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Winnipeg (YWG)
8.2/10 Very Good! (1,236 reviews)
Was right for my business needs

Reviewed on Jun 29, 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
$116 nightly
The price is $130 total per night from Jul 14 to Jul 15
$130 total
Jul 14 - Jul 15
Total includes taxes and fees
8.8/10 Excellent! (1,005 reviews)
"Awesome experience-Awesome service"

Reviewed on Jun 30, 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
$113 nightly
The price is $127 total per night from Jul 27 to Jul 28
$127 total
Jul 27 - Jul 28
Total includes taxes and fees
9/10 Wonderful! (1,118 reviews)
"Easy access to the highway as we were there to join the every child matters bike ride .. very nice"

Reviewed on Jun 29, 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
$122 nightly
The price is $144 total per night from Jul 21 to Jul 22
$144 total
Jul 21 - Jul 22
Total includes taxes and fees
8.4/10 Very Good! (2,086 reviews)
"Great!"

Reviewed on Jun 28, 2025

Victoria Inn Hotel and Convention Centre Winnipeg
See all 520 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 $858 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.