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 Fort Garry

Canad Inns Destination Centre Fort Garry

3 out of 5
Fort Garry
per person
Sep 30 - Oct 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Winnipeg (YWG)
8/10 Very Good! (1,032 reviews)
It was good, i would stay again

Reviewed on Aug. 6, 2025

Humphry Inn & Suites

Humphry Inn & Suites

2.5 out of 5
Downtown Winnipeg
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Winnipeg (YWG)
8.2/10 Very Good! (1,301 reviews)
There is a parking fee and it should be mentioned while booking.

Reviewed on Aug. 5, 2025

Canad Inns Destination Centre Polo Park

Canad Inns Destination Centre Polo Park

3 out of 5
Polo Park
per person
Sep 30 - Oct 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Winnipeg (YWG)
7.8/10 Good! (1,004 reviews)
Nice room Good shower Check in quick

Reviewed on Jul. 20, 2025

Canad Inns Destination Centre Transcona

Canad Inns Destination Centre Transcona

3 out of 5
Transcona
per person
Sep 30 - Oct 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Winnipeg (YWG)
8.2/10 Very Good! (1,000 reviews)
Our stay was good, everything was goodexcept when we were checking out, there was a drunk msn outside making a scene and there were police, was so scary. But everything was excellent. Will definitely go back.

Reviewed on Aug. 5, 2025

Canad Inns Destination Centre Club Regent Casino Hotel

Canad Inns Destination Centre Club Regent Casino Hotel

3 out of 5
Transcona
per person
Sep 30 - Oct 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Winnipeg (YWG)
9/10 Wonderful! (1,241 reviews)
Super friendly staff, very convenient and comfortable. Overall would reccomend and will stay again in the future

Reviewed on Aug. 5, 2025

Ready to book your vacation to Headingley?

 

Choose your dates

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
The price is CA $159 per night from Aug 24 to Aug 25
CA $159
CA $178 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (1,008 reviews)
"The room was spacious and clean. The bed was comfortable."

Reviewed on Aug. 3, 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
The price is CA $155 per night from Aug 21 to Aug 22
CA $155
CA $174 total
Aug 21 - Aug 22
includes taxes & fees
9/10 Wonderful! (1,129 reviews)
"This is the best Motel 6 we’ve ever stayed in. If you’re on road trip across Canada, location is very convenience. Just on highway and close to shops. Room is very clean and comfortable. Staff is very friendly. Plenty of parking space, there’s security also, so it’s safe. There was free slurpee, ..."

Reviewed on Aug. 4, 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
The price is CA $190 per night from Aug 7 to Aug 8
CA $190
CA $225 total
Aug 7 - Aug 8
includes taxes & fees
8.6/10 Excellent! (1,221 reviews)
"Very nice"

Reviewed on Aug. 5, 2025

Birchwood Inn, BW Premier Collection
See all 515 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
Beach Vacations
Family Vacations
Family Vacations

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

Thunder Rapids Fun Park

Bring the kiddos to Thunder Rapids Fun Park and enjoy some excitement at this theme park in Headingley. Stroll along the riverfront or attend a sporting event in the area.

Thunder Rapids Fun Park

Frequently asked questions

How much does a Headingley vacation package cost?
You can snap up a vacation package to this top destination from CA $409 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.

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