Headingley Vacation Packages

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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.

Top Headingley Vacation Deals

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 CA $403, price is now CA $332 per person
CA $332
per person
Sep 9 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Winnipeg (YWG)
8.2/10 Very good! (1,004 reviews)
Jonathan Blain went beyond the expected service. When he saw that I was a retired Service Member he sought out ways to improve our stay and then some. He even provided us with a breakfast coupon. Jonathan sets the bar for others to achieve. Bravo Zulu to this gentlemen.

Reviewed on Jul 8, 2026

Canad Inns Destination Centre Club Regent Casino Hotel

Canad Inns Destination Centre Club Regent Casino Hotel

3 out of 5
Transcona
Price was CA $495, price is now CA $395 per person
CA $395
per person
Sep 9 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Winnipeg (YWG)
9/10 Wonderful! (1,695 reviews)
Very good stay

Reviewed on Jul 6, 2026

Humphry Inn & Suites

Humphry Inn & Suites

2.5 out of 5
Downtown Winnipeg
Price was CA $841, price is now CA $683 per person
CA $683
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Winnipeg (YWG)
8.4/10 Very good! (1,633 reviews)
I like cleaning but bathroom fan was not working and there was a bad smell on beds.

Reviewed on Jul 7, 2026

Canad Inns Destination Centre Transcona

Canad Inns Destination Centre Transcona

3 out of 5
Transcona
Price was CA $540, price is now CA $440 per person
CA $440
per person
Sep 9 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Winnipeg (YWG)
8.4/10 Very good! (1,007 reviews)
Room is pretty clean and tidy

Reviewed on Jul 6, 2026

Canad Inns Destination Centre Fort Garry

Canad Inns Destination Centre Fort Garry

3 out of 5
Fort Garry
Price was CA $873, price is now CA $714 per person
CA $714
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Winnipeg (YWG)
8/10 Very good! (1,351 reviews)
The staff made check in and out very easy.

Reviewed on Jul 8, 2026

Ready to book your vacation to Headingley?

 

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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
The price is CA $172 per night from Jul 21 to Jul 22
CA $172
CA $193 total
Jul 21 - Jul 22
includes taxes & fees
9.2/10 Wonderful! (1,567 reviews)
"Very friendly clean hotel."

Reviewed on Jul 7, 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
The price is CA $184 per night from Jul 26 to Jul 27
CA $184
CA $206 total
Jul 26 - Jul 27
includes taxes & fees
9/10 Wonderful! (1,008 reviews)
"Room was clean and they let us check in a little early so we didn’t have to wander the city. Much appreciated!"

Reviewed on Jul 5, 2026

Best Western Plus Winnipeg West
The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel

The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel

4 out of 5
222 Broadway Winnipeg MB
Fully refundable
The price is CA $195 per night from Aug 7 to Aug 8
CA $195
CA $230 total
Aug 7 - Aug 8
includes taxes & fees
9.2/10 Wonderful! (1,225 reviews)
"Loved!"

Reviewed on Jul 8, 2026

The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel
See all 661 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Stay near popular Headingley attractions

John Blumberg Softball Complex

8.0/10 (13 reviews)
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.
See properties

Frequently asked questions

How much does a Headingley vacation package cost?
You can snap up a vacation package to this top destination from CA $332 on Expedia. But how much your vacation to Headingley costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Headingley?
If you're looking to snag a cheap Headingley vacation package, consider travelling in January, October and November. You'll typically find lower prices on flights and hotels during these quieter months — perfect for budget-conscious travellers.
How many days is enough for Headingley?
To get the most out of a Headingley vacation, we recommend staying for 2 days. Divide your time between visiting BellMTS Iceplex, Academy Lanes West and other major sights, in addition to experiencing neighbourhoods like Westdale and Buchanan. If you've got some spare time, add a day trip to your Headingley vacation itinerary.
Is it worth booking a vacation package to Headingley?
Headingley offers everything you need for an amazing escape. Get your Headingley vacation off to a flying start by visiting major attractions like BellMTS Iceplex.
How to find the best Headingley package deals?
Use Expedia's filter tool to find some terrific Headingley package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or look for Headingley package deals in the low season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Headingley vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and stays individually. Better still, you can customize your Headingley escape to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Headingley?
If you have your Headingley travel dates finalized, book early to grab some awesome deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are ideal for setting off on a whim.
How to plan a trip to Headingley?

  1. Choose your dates: What you want to do in Headingley and your preferred season can help you decide when to go.
  2. Figure out your budget: Ensure you have enough money to cover everything from transportation and dining out to experiences and flights. Your hotel will probably be the largest expense during your trip to Headingley.
  3. Decide your trip length: Think about how much time you want to spend discovering Headingley. Plan your days so you can get to all the attractions and activities you're interested in without rushing.
  4. Combine your airfare and accommodations: After you've nailed down your travel dates and duration, lock in the perfect Headingley vacation package for you.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.