Headingley Vacations from $622

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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 $760, price is now $622 per person
$622
per person
Feb 23 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Seattle (SEA) to Winnipeg (YWG)
8/10 Very Good! (1,001 reviews)
Breakfast was good, should have Breakfast specials everyday

Reviewed on Jan 21, 2026

Humphry Inn & Suites

Humphry Inn & Suites

2.5 out of 5
Downtown Winnipeg
Price was $963, price is now $754 per person
$754
per person
Feb 23 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Seattle (SEA) to Winnipeg (YWG)
8.2/10 Very Good! (1,479 reviews)
Very friendly service.. very clean . Could have better pillows

Reviewed on Jan 18, 2026

Canad Inns Destination Centre Polo Park

Canad Inns Destination Centre Polo Park

3 out of 5
Polo Park
Price was $893, price is now $714 per person
$714
per person
Feb 23 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Seattle (SEA) to Winnipeg (YWG)
7.8/10 Good! (1,002 reviews)
Very close to Polo Park mall.

Reviewed on Jan 20, 2026

Canad Inns Destination Centre Fort Garry

Canad Inns Destination Centre Fort Garry

3 out of 5
Fort Garry
Price was $826, price is now $668 per person
$668
per person
Feb 23 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Seattle (SEA) to Winnipeg (YWG)
8/10 Very Good! (1,105 reviews)
Found ourselves stuck in Winnipeg to to a storm which shut down all of southern Manitoba. Desk staff was very good. The room itself left something to be desired as far as cleanliness goes. Found a false eyelash on the vanity stuck to the tissue box and a hairband on the floor along with several white fuzzies. Could also see that things had been lightly dusted as there was a spot under each TV leg that had not been addressed for a while. Resturant service and food was good and attentive. Housekeeping needs to step up their game.

Reviewed on Jan 17, 2026

Canad Inns Destination Centre Transcona

Canad Inns Destination Centre Transcona

3 out of 5
Transcona
Price was $783, price is now $638 per person
$638
per person
Feb 23 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Seattle (SEA) to Winnipeg (YWG)
8.4/10 Very Good! (1,001 reviews)
Friendly welcome with quick check in. Room clean and well organized. Inviting and relaxing.

Reviewed on Jan 20, 2026

Don't see what you're looking for?
See all available trips from Columbus to Headingley
View all trips

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
$82 nightly
The price is $91 total per night from Jan 25 to Jan 26
$91 total
Jan 25 - Jan 26
Total with taxes and fees
9/10 Wonderful! (1,323 reviews)
Clean quiet place. Easy to get to shopping centre.

Reviewed on Jan 16, 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
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $141 total per night from Feb 8 to Feb 9
$141 total
Feb 8 - Feb 9
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
Rooms were nice and clean. Most of the staff were pleasant and good to deal with.

Reviewed on Jan 11, 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
$120 nightly
The price is $142 total per night from Feb 22 to Feb 23
$142 total
Feb 22 - Feb 23
Total with taxes and fees
8.4/10 Very Good! (2,728 reviews)
Close to airport

Reviewed on Jan 17, 2026

Victoria Inn Hotel and Convention Centre Winnipeg
See all 554 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Headingley vacation package cost?
You can pick up a vacation package to this top destination from $622 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.