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 $605, price is now CA $487 per person
CA $487
per person
Feb 4 - Feb 7
found 22 hours ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
8.2/10 Very good! (1,005 reviews)

Canad Inns Destination Centre Transcona

Canad Inns Destination Centre Transcona

3 out of 5
Transcona
Price was CA $663, price is now CA $519 per person
CA $519
per person
Feb 4 - Feb 7
found 22 hours ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
8.4/10 Very good! (1,004 reviews)

Humphry Inn & Suites

Humphry Inn & Suites

2.5 out of 5
Downtown Winnipeg
Price was CA $727, price is now CA $580 per person
CA $580
per person
Feb 4 - Feb 7
found 22 hours ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
8.4/10 Very good! (1,756 reviews)
Stayed here while traveling for business. Location is good for downtown trips, but hotel is dated and room had a mild, musty smell, but was clean. Air conditioning in room was loud while on. Breakfast buffet was good enough. Staff was very friendly. Overall, I would stay here again when traveling for work.

Reviewed on Nov 13, 2026

Country Inn & Suites by Radisson, Winnipeg, MB

Country Inn & Suites by Radisson, Winnipeg, MB

2.5 out of 5
St. James
Price was CA $720, price is now CA $596 per person
CA $596
per person
Feb 4 - Feb 7
found 22 hours ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
7.6/10 Good! (1,002 reviews)

Canad Inns Destination Centre Windsor Park

Canad Inns Destination Centre Windsor Park

3 out of 5
Windsor Park
Price was CA $610, price is now CA $505 per person
CA $505
per person
Feb 4 - Feb 7
found 22 hours ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
8/10 Very good! (1,004 reviews)
Very clean and well maintained rooms Lots of stairs to navigate. Convenient location.

Reviewed on Nov 14, 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 $120 per night from Nov 29 to Nov 30
CA $120
CA $134 total
Nov 29 - Nov 30
includes taxes & fees
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 $201 per night from Nov 29 to Nov 30
CA $201
CA $225 total
Nov 29 - Nov 30
includes taxes & fees
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
The price is CA $139 per night from Dec 15 to Dec 16
CA $139
CA $165 total
Dec 15 - Dec 16
includes taxes & fees
8.4/10 Very good! (3,353 reviews)
"Great place Excellent price"

Reviewed on Nov 14, 2026

Victoria Inn Hotel and Convention Centre Winnipeg
See all 707 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
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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 $487 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.