Headingley Vacations from $357

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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 Fort Garry

Canad Inns Destination Centre Fort Garry

3 out of 5
Fort Garry
Price was $452, price is now $357 per person
$357
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Winnipeg (YWG)
7.8/10 Good! (1,059 reviews)
One of few places that have 2 real bedrooms with doors and a common sitting area. We didnt eat there or check out the water park. Just a stop to sleep. Common hallway carpet could definitely be replaced. Room darkening shade in one bedroom was broken and lots of street lights so a bit hard to fall asleep.

Reviewed on Aug 22, 2025

Humphry Inn & Suites

Humphry Inn & Suites

2.5 out of 5
Downtown Winnipeg
Price was $494, price is now $379 per person
$379
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Winnipeg (YWG)
8.2/10 Very Good! (1,329 reviews)
Convenient location

Reviewed on Aug 23, 2025

Canad Inns Destination Centre Club Regent Casino Hotel

Canad Inns Destination Centre Club Regent Casino Hotel

3 out of 5
Transcona
Price was $502, price is now $387 per person
$387
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Winnipeg (YWG)
9/10 Wonderful! (1,263 reviews)
Check in staff was nice and kind but the room was smelly when I went in. The hair dryer was old(seemed dangerous) and too noisy.

Reviewed on Aug 20, 2025

Canad Inns Destination Centre Transcona

Canad Inns Destination Centre Transcona

3 out of 5
Transcona
Price was $466, price is now $365 per person
$365
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Winnipeg (YWG)
8.2/10 Very Good! (1,011 reviews)
An older hotel… But kept up. Quite clean. The service in the pub was fantastic… As was the service for breakfast the next day. Males in both the pub and the restaurant were excellent!

Reviewed on Aug 23, 2025

Canad Inns Destination Centre Polo Park

Canad Inns Destination Centre Polo Park

3 out of 5
Polo Park
Price was $454, price is now $358 per person
$358
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Winnipeg (YWG)
7.8/10 Good! (1,001 reviews)
This was a convenient place to stay while going to the airport in the early morning. Would stay again if looking for an airport hotel!

Reviewed on Aug 20, 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
$114 nightly
The price is $128 total per night from Sep 9 to Sep 10
$128 total
Sep 9 - Sep 10
Total with taxes and fees
8.8/10 Excellent! (1,009 reviews)
"Excellent pool for young kids."

Reviewed on Aug 19, 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
$107 nightly
The price is $120 total per night from Sep 3 to Sep 4
$120 total
Sep 3 - Sep 4
Total with taxes and fees
9/10 Wonderful! (1,136 reviews)
"The warm friendly environment"

Reviewed on Aug 20, 2025

Motel 6 Headingley, MB - Winnipeg West
Birchwood Inn, BW Premier Collection

Birchwood Inn, BW Premier Collection

3 out of 5
2520 Portage Ave, Winnipeg, MB
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $149 total per night from Sep 9 to Sep 10
$149 total
Sep 9 - Sep 10
Total with taxes and fees
8.6/10 Excellent! (1,230 reviews)
"Good"

Reviewed on Aug 21, 2025

Birchwood Inn, BW Premier Collection
See all 478 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.

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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 $357 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.