Headingley Vacations from $479

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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.
Victoria Inn Hotel and Convention Centre Winnipeg

Victoria Inn Hotel and Convention Centre Winnipeg

3 out of 5
St. James
Price was $650, price is now $479 per person
$479
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Winnipeg (YWG)
8.4/10 Very Good! (2,464 reviews)
Quiet hotel stayed as a family with toddler pool was really nice for younger kids small slides and shallow end for young kids plus a big slide for bigger kids and hottub. room was spacious and clean

Reviewed on Dec 17, 2025

Humphry Inn & Suites

Humphry Inn & Suites

2.5 out of 5
Downtown Winnipeg
Price was $856, price is now $738 per person
$738
per person
Feb 13 - Feb 16
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Winnipeg (YWG)
8.2/10 Very Good! (1,479 reviews)
I have stayed in nicer hotels for less. Needs some updating. Parking was extra. It was noisy. We had to turn the fan on to help drown out the traffic. Staff were good, friendly, and helpful.

Reviewed on Dec 15, 2025

Canad Inns Destination Centre Fort Garry

Canad Inns Destination Centre Fort Garry

3 out of 5
Fort Garry
Price was $835, price is now $730 per person
$730
per person
Feb 13 - Feb 16
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Winnipeg (YWG)
8/10 Very Good! (1,105 reviews)
The only thing negative that we found was the tile floors in room were not very clean. A good daily swiffer would do wonders. Other than that all was good.

Reviewed on Dec 17, 2025

Viscount Gort Hotel

Viscount Gort Hotel

3 out of 5
Price was $585, price is now $512 per person
$512
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Winnipeg (YWG)
7.2/10 Good! (1,105 reviews)
Restaurant and bar was closed

Reviewed on Dec 17, 2025

The Fairmont Winnipeg Gold Experience

The Fairmont Winnipeg Gold Experience

4 out of 5
Exchange District
Price was $1,091, price is now $958 per person
$958
per person
Feb 13 - Feb 16
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Winnipeg (YWG)
8.6/10 Excellent! (30 reviews)
Enjoyed the Fairmont Gold Experience. Gold Lounge was closed for renovations on our last day, but the hotel took great care of us in the restaurant for breakfast. We will be back.

Reviewed on Feb 5, 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 refundable
$74 nightly
The price is $83 total per night from Jan 5 to Jan 6
$83 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
9/10 Wonderful! (1,254 reviews)
All good

Reviewed on Dec 10, 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
$127 nightly
The price is $142 total per night from Jan 1 to Jan 2
$142 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
Clean, great staff, pool is fabulous for kids

Reviewed on Dec 6, 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
$97 nightly
The price is $115 total per night from Dec 21 to Dec 22
$115 total
Dec 21 - Dec 22
Total with taxes and fees
8.4/10 Very Good! (2,578 reviews)
Good

Reviewed on Dec 12, 2025

Victoria Inn Hotel and Convention Centre Winnipeg
See all 535 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 $479 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.