Title: Headingley Vacation Packages & Trips 2026 from CA $343 | Expedia.ca

[Headingley Travel Guide](https://expedia.ca/Headingley.dx6145346)[Hotels in Headingley](https://expedia.ca/Headingley-Hotels.d6145346.Travel-Guide-Hotels)[Vacation Rentals in Headingley](https://expedia.ca/Headingley-Vacation-Rentals.d6145346.Travel-Guide-VacationRentals)[Flights to Headingley](https://expedia.ca/Cheap-Flights-To-Headingley.d6145346.Travel-Guide-Flights)[Headingley Car Rentals](https://expedia.ca/Car-Rentals-In-Headingley.d6145346.Car-Rental-Guide)

![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium)

# Headingley Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to CA $1,096 when you book a flight and hotel together\*
- ###  
Find the right fit  
With over 300,000 hotels worldwide, it's easy to create a perfect package
- ###  
Rest easy  
Plan, book, and manage your trip all in one place

#### 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](https://www.expedia.ca/Assiniboia-Downs-Winnipeg.d6229713.Vacation-Attraction), [BellMTS Iceplex](https://www.expedia.ca/BellMTS-Iceplex-Winnipeg.d553248635026762217.Vacation-Attraction) and [Unicity Mall](https://www.expedia.ca/Unicity-Mall-Winnipeg.d553248621585428171.Vacation-Attraction), 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 Transcona](https://images.trvl-media.com/lodging/6000000/5430000/5424800/5424791/ade61ad2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Canad Inns Destination Centre Transcona

Transcona

CA $343

per person

Mar 18 - Mar 20

found 16 hours ago

Roundtrip flight included

Edmonton (YEG) to Winnipeg (YWG)

8.4/10 Very Good! (1,001 reviews)

Great place to stay.

Reviewed on Jan 26, 2026

![Humphry Inn & Suites](https://images.trvl-media.com/lodging/1000000/860000/857300/857263/b2dc02ef_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Humphry Inn & Suites

Downtown Winnipeg

CA $357

per person

Mar 18 - Mar 20

found 16 hours ago

Roundtrip flight included

Edmonton (YEG) to Winnipeg (YWG)

8.2/10 Very Good! (1,479 reviews)

great staff, rooms basic but just what is needed

Reviewed on Jan 26, 2026

![Canad Inns Destination Centre Polo Park](https://images.trvl-media.com/lodging/1000000/700000/694300/694214/d40e5d16_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Canad Inns Destination Centre Polo Park

Polo Park

CA $353

per person

Mar 18 - Mar 20

found 16 hours ago

Roundtrip flight included

Edmonton (YEG) to Winnipeg (YWG)

7.8/10 Good! (1,002 reviews)

Very close to Polo Park mall.

Reviewed on Jan 20, 2026

![Canad Inns Destination Centre Fort Garry](https://images.trvl-media.com/lodging/1000000/60000/53000/52976/66851e8c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Canad Inns Destination Centre Fort Garry

Fort Garry

CA $345

per person

Mar 18 - Mar 20

found 16 hours ago

Roundtrip flight included

Edmonton (YEG) to Winnipeg (YWG)

8/10 Very Good! (1,105 reviews)

Found ourselves stuck in Winnipeg to to a storm which shut down all of southern Manitoba. Desk staff was very good. The room itself left something to be desired as far as cleanliness goes. Found a false eyelash on the vanity stuck to the tissue box and a hairband on the floor along with several white fuzzies. Could also see that things had been lightly dusted as there was a spot under each TV leg that had not been addressed for a while. Resturant service and food was good and attentive. Housekeeping needs to step up their game.

Reviewed on Jan 17, 2026

![Canad Inns Destination Centre Club Regent Casino Hotel](https://images.trvl-media.com/lodging/1000000/590000/583700/583630/c7554b08_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Canad Inns Destination Centre Club Regent Casino Hotel

Transcona

CA $357

per person

Mar 18 - Mar 20

found 16 hours ago

Roundtrip flight included

Edmonton (YEG) to Winnipeg (YWG)

9/10 Wonderful! (1,380 reviews)

Room was clean..staff was friendly, only stayed here cause the casino was here.

Reviewed on Jan 26, 2026

## Ready to book your vacation to Headingley?

Choose your dates

## Headingley Hotel Deals

![Motel 6 Headingley, MB - Winnipeg West](https://images.trvl-media.com/lodging/5000000/4470000/4464100/4464039/56e2f620_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Motel 6 Headingley, MB - Winnipeg West

4400 Portage Avenue Headingley MB

Fully refundableReserve now, pay when you stay

CA $113

CA $127 total

Feb 8 - Feb 9

includes taxes & fees

9/10 Wonderful! (1,339 reviews)

T

Reviewed on Jan 22, 2026

[](https://expedia.ca/Hotel-Search?startDate=08%2F02%2F2026&endDate=09%2F02%2F2026&selected=4464039&PinnedHotelID=4464039&HadPinnedHotel=true&regionId=6145346)

![Best Western Plus Winnipeg West](https://images.trvl-media.com/lodging/8000000/7460000/7450600/7450581/f06a9fda_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Best Western Plus Winnipeg West

4140 Portage Avenue Headingley MB

Fully refundableReserve now, pay when you stay

CA $175

CA $196 total

Feb 9 - Feb 10

includes taxes & fees

8.8/10 Excellent! (1,004 reviews)

Rooms were nice and clean. Most of the staff were pleasant and good to deal with.

Reviewed on Jan 11, 2026

[](https://expedia.ca/Hotel-Search?startDate=09%2F02%2F2026&endDate=10%2F02%2F2026&selected=7450581&PinnedHotelID=7450581&HadPinnedHotel=true&regionId=6145346)

![Victoria Inn Hotel and Convention Centre Winnipeg](https://images.trvl-media.com/lodging/1000000/20000/13300/13226/94dbadb8_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Victoria Inn Hotel and Convention Centre Winnipeg

1808 Wellington Ave Winnipeg MB

Fully refundableReserve now, pay when you stay

CA $167

CA $197 total

Feb 22 - Feb 23

includes taxes & fees

8.4/10 Very Good! (2,757 reviews)

Staff was courteous to resolve the issue in the room.. was clean and comfortable

Reviewed on Jan 24, 2026

[](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=13226&PinnedHotelID=13226&HadPinnedHotel=true&regionId=6145346)

[See all 560 properties in Headingley](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=27%2F01%2F2026&endDate=28%2F01%2F2026&regionId=6145346)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

### 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. 

[](https://expedia.ca/John-Blumberg-Softball-Complex-Headingley.d6255853.Vacation-Attraction)

#### 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. 

[](https://expedia.ca/Thunder-Rapids-Fun-Park-Headingley.d553248621561234992.Vacation-Attraction)

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- [U-Puttz Thrill Zone ](https://www.expedia.ca/U-Puttz-Thrill-Zone-Winnipeg.d553248621532864894.Vacation-Attraction)
- [Unicity Mall ](https://www.expedia.ca/Unicity-Mall-Winnipeg.d553248621585428171.Vacation-Attraction)
- [University of Winnipeg ](https://www.expedia.ca/University-Of-Winnipeg-Winnipeg.d6072399.Vacation-Attraction)
- [Visit Birchwood ](https://www.expedia.ca/Winnipeg-Birchwood.dx873287256046260224)
- [Visit Westdale ](https://www.expedia.ca/Winnipeg-Westdale.dx873292502896168960)
- [Winnipeg Vacations ](https://www.expedia.ca/Winnipeg.d6141041.Destination-Travel-Guides)

- [Car rentals near Academy Lanes West ](https://www.expedia.ca/Car-Rentals-In-Academy-Lanes-West.d642299788980453376.Car-Rental-Guide)
- [Rental cars Winnipeg James Armstrong Richardson Intl. airport ](https://www.expedia.ca/Car-Rentals-In-Winnipeg-James-Armstrong-Richardson-Intl.d4675417.Car-Rental-Guide)
- [Car rentals near Winnipeg ](https://www.expedia.ca/Car-Rentals-In-Winnipeg.d6141041.Car-Rental-Guide)

- [Things to do in Winnipeg ](https://www.expedia.ca/Things-To-Do-In-Winnipeg.d6141041.Travel-Guide-Activities)

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

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