Headingley Vacations from $569

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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.
Humphry Inn & Suites

Humphry Inn & Suites

2.5 out of 5
Downtown Winnipeg
Price was $692, price is now $569 per person
$569
per person
Jun 25 - Jun 28
found 1 hour ago
Roundtrip non-stop flight included
Houston (IAH) to Winnipeg (YWG)
8.4/10 Very Good! (1,580 reviews)
Clean room, kind staff, and nice to have a continental breakfast.

Reviewed on Mar 29, 2026

Canad Inns Destination Centre Fort Garry

Canad Inns Destination Centre Fort Garry

3 out of 5
Fort Garry
Price was $948, price is now $739 per person
$739
per person
Jun 9 - Jun 15
found 18 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Winnipeg (YWG)
8/10 Very Good! (1,218 reviews)
Great bed, comfy pillows! Breakfast is great... staff are very friendly and helpful

Reviewed on Mar 31, 2026

Canad Inns Destination Centre Transcona

Canad Inns Destination Centre Transcona

3 out of 5
Transcona
Price was $686, price is now $569 per person
$569
per person
Jun 25 - Jun 28
found 1 hour ago
Roundtrip non-stop flight included
Houston (IAH) to Winnipeg (YWG)
8.4/10 Very Good! (1,012 reviews)
The room was clean and the property has everything you need a restaurant and a swimming pool

Reviewed on Mar 28, 2026

Victoria Inn Hotel and Convention Centre Winnipeg

Victoria Inn Hotel and Convention Centre Winnipeg

3 out of 5
St. James
Price was $920, price is now $777 per person
$777
per person
May 21 - May 25
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Winnipeg (YWG)
8.4/10 Very Good! (2,863 reviews)
Checked in later. Super courteous staff. Also left early so can’t comment on much more than room. I was not impressed with noise in hallways on middle of nite 9”otherwise our experience was okay

Reviewed on Mar 31, 2026

Inn At The Forks

Inn At The Forks

3.5 out of 5
Downtown Winnipeg
Price was $1,330, price is now $1,124 per person
$1,124
per person
May 21 - May 25
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Winnipeg (YWG)
9/10 Wonderful! (1,001 reviews)
Very nice stay! Room was beautiful with a great view! Very clean and staff were wonderful

Reviewed on Mar 31, 2026

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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
$92 nightly
The price is $103 total per night from Apr 30 to May 1
$103 total
Apr 30 - May 1
Total with taxes and fees
9.2/10 Wonderful! (1,413 reviews)
A microwave in the room would be an excellent upgrade as there isnt any restaurant on site or walking distance

Reviewed on Mar 31, 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
$141 nightly
The price is $158 total per night from Apr 30 to May 1
$158 total
Apr 30 - May 1
Total with taxes and fees
9/10 Wonderful! (1,003 reviews)
All around awesome stay

Reviewed on Mar 30, 2026

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
$116 nightly
The price is $137 total per night from Apr 5 to Apr 6
$137 total
Apr 5 - Apr 6
Total with taxes and fees
8.4/10 Very Good! (2,916 reviews)
Room was small but cleaned. Ceiling could use a paint job, scuffs around the door and on the ceiling paint peeling Floor was quiet, easy access to elevator

Reviewed on Apr 1, 2026

Victoria Inn Hotel and Convention Centre Winnipeg
See all 615 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 $569 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.