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.
Victoria Inn Hotel and Convention Centre Winnipeg

Victoria Inn Hotel and Convention Centre Winnipeg

3 out of 5
St. James
per person
Jun. 19 - Jun. 23
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
8.4/10 Very Good! (1,884 reviews)
I like the pool that’s about it

Reviewed on Apr. 29, 2025

Sandman Hotel & Suites Winnipeg Airport

Sandman Hotel & Suites Winnipeg Airport

3 out of 5
St. James
Save 100% on your flight
per person
Jun. 19 - Jun. 23
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
8.2/10 Very Good! (1,160 reviews)
Was my first time staying there and it wasn't bad, only downside was the pool thing was small. Would stay there again for sure.

Reviewed on Apr. 28, 2025

Canad Inns Destination Centre Fort Garry

Canad Inns Destination Centre Fort Garry

3 out of 5
Fort Garry
per person
Jun. 19 - Jun. 23
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
7.8/10 Good! (1,009 reviews)
Day was cold and windy so lots of dust and debris flying around. Room is clean so all is good.

Reviewed on Apr. 29, 2025

Canad Inns Destination Centre Transcona

Canad Inns Destination Centre Transcona

3 out of 5
Transcona
per person
Jun. 19 - Jun. 23
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
8/10 Very Good! (971 reviews)
A better shower head is needed.

Reviewed on Apr. 14, 2025

Canad Inns Destination Centre Polo Park

Canad Inns Destination Centre Polo Park

3 out of 5
Polo Park
per person
Jun. 19 - Jun. 23
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
7.6/10 Good! (1,002 reviews)
Room was nice and clean

Reviewed on Apr. 30, 2025

Ready to book your vacation to Headingley?

 

Choose your dates

Headingley Hotel Deals

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 $103 per night from May 5 to May 6
CA $103
CA $116 total
includes taxes & fees
May 5 - May 6
9/10 Wonderful! (1,046 reviews)
"Clean, updated motel"

Reviewed on Apr. 29, 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
The price is CA $157 per night from May 14 to May 15
CA $157
CA $175 total
includes taxes & fees
May 14 - May 15
8.8/10 Excellent! (1,000 reviews)
"We stayed in the middle of the week & it was nice and quiet. The breakfast was ok (same as every other hotel with free breakfast). The only thing was the chlorine in the hot tub/pool was SO strong, our eyes were burning, so we only stayed in for a few minutes. Staff were friendly. Really appreciated ..."

Reviewed on Apr. 28, 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
The price is CA $133 per night from May 19 to May 20
CA $133
CA $158 total
includes taxes & fees
May 19 - May 20
8.4/10 Very Good! (1,976 reviews)
"Very clean, elevators oddly located. Pool was warm, kids enjoyed. Lack of parental supervision an issue in pool area. Plenty of towels for everyone."

Reviewed on Apr. 27, 2025

Victoria Inn Hotel and Convention Centre Winnipeg
See all 514 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

Frequently asked questions

How much does a Headingley vacation package cost?
You can snap up a vacation package to this top destination from CA $476 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.

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