Headingley Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

    Plan, book, travel with confidence
  • payments icon
    Better together
    Save up to CA $775 when you book a flight and hotel together*
  • lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • lob packages icon
    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, 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

Humphry Inn & Suites

Humphry Inn & Suites

2.5 out of 5
Downtown Winnipeg
per person
May 28 - May 31
Roundtrip flight included
Calgary (YYC) to Winnipeg (YWG)
8.4/10 Very Good! (1,015 reviews)
Parking, swimming pool not working

Reviewed on Apr. 17, 2024

Canad Inns Destination Centre Polo Park

Canad Inns Destination Centre Polo Park

3 out of 5
Polo Park
per person
May 28 - May 31
Roundtrip flight included
Calgary (YYC) to Winnipeg (YWG)
7.4/10 Good! (1,002 reviews)
Enjoyed my stay met all my needs

Reviewed on Apr. 16, 2024

Canad Inns Destination Centre Garden City

Canad Inns Destination Centre Garden City

3 out of 5
Leila-McPhillips Triangle
per person
May 28 - May 31
Roundtrip flight included
Calgary (YYC) to Winnipeg (YWG)
8/10 Very Good! (1,001 reviews)
My stay at the hotel was great overall. The service, room, and amenities were excellent. However, the lack of provided slippers was disappointing. Hopefully, they'll consider adding this in the future.

Reviewed on Apr. 16, 2024

Canad Inns Destination Centre Transcona

Canad Inns Destination Centre Transcona

3 out of 5
Transcona
per person
May 28 - May 31
Roundtrip flight included
Calgary (YYC) to Winnipeg (YWG)
8/10 Very Good! (773 reviews)
The hospitality of the cleanliness.

Reviewed on Apr. 4, 2024

Canad Inns Destination Centre Fort Garry

Canad Inns Destination Centre Fort Garry

3 out of 5
Fort Garry
per person
May 28 - May 31
Roundtrip flight included
Calgary (YYC) to Winnipeg (YWG)
8/10 Very Good! (1,005 reviews)
The people were friendly and it was a good experience all around.

Reviewed on Apr. 15, 2024

Prices and availability subject to change. Additional terms may apply.

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 $130 per night from Apr. 21 to Apr. 22
CA $130
CA $146 total
includes taxes & fees
Apr 21 - Apr 22
8.8/10 Excellent! (1,001 reviews)
"Can not turn off the highway coming from the east. You have to drive further west and make a u-turn at the next light on highway nr 1. Everything else is fine"

Reviewed on Apr. 17, 2024

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 $161 per night from May 5 to May 6
CA $161
CA $180 total
includes taxes & fees
May 5 - May 6
8.6/10 Excellent! (1,002 reviews)
"Great hospitality"

Reviewed on Apr. 17, 2024

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 $156 per night from Apr. 24 to Apr. 25
CA $156
CA $185 total
includes taxes & fees
Apr 24 - Apr 25
8.2/10 Very Good! (1,280 reviews)
"All the staff were very friendly and helpful"

Reviewed on Apr. 16, 2024

Victoria Inn Hotel and Convention Centre Winnipeg
See all 508 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.

Explore other types of vacation packages

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?
Our Headingley packages, which begin at just CA $402, are an ideal way to save precious money. Pick your preferred flights, hotels and rental cars to create a customized itinerary.
How do I get a cheap travel package to Headingley?
If you love getting an amazing deal, combine your bookings into a Headingley vacation package. Whether you’re looking for hotels, flights, tours or rental cars, you can book everything in one place. You’ll have endless choice at your fingertips as well. Expedia has over 550 airlines and 1,000,000 properties all over the world to choose from. Fly with who you want, find a room where you like and save precious dollars — now that’s the perfect getaway!
Where should I stay in Headingley?
Stay where the action happens. Many travelers book hotels within easy reach of popular sights, like Red River Exhibition Park, BellMTS Iceplex and Thunder Rapids Fun Park.
What are the top hotels in Headingley?
Get your trip off to a flying start by staying at Motel 6 Headingley, MB - Winnipeg West. It’s one of most popular properties in Headingley. Another top option is Best Western Plus Winnipeg West.
How far in advance should I book my Headingley vacation?
Earlier is always better. Airlines generally advertise flight tickets up to a year ahead of departure, and this is a fantastic opportunity to score some of the cheapest prices. Just been told you need to take all your vacation days next week? That’s alright! Expedia are never short on fantastic deals to whisk you away on the getaway of your dreams, at an affordable price.
What does an Expedia Headingley travel package include?
Much of that depends on you. You can choose from a variety of Headingley packages, such as a flight, hotel and rental car. You can also book a hotel with a flight, or a flight with a rental car. Once you’ve made your booking, you can add the fun stuff like tours and activities. Whatever your ideal Headingley vacation looks like, get ready to save!
What should I know before booking a Headingley travel package?
A travel package can be tailored to your budget and is a fantastic way to stretch your dollars further. What you include is your call. Hotels, rental cars and flights — decide on a combination that suits your style.
Can I choose my airline with a Headingley Expedia vacation package?
The choice is all yours! Expedia has access to more than 550 partner airlines worldwide, so you can tailor your Headingley escape according to your travel preferences.
If I'm not able to travel, can I cancel my Headingley vacation package?
Whether it’s your flight or hotel, you can cancel and rebook it. Booked your Headingley vacation package in the last 24 hours? You may be able to make changes for free. For older bookings, you may incur a charge from your hotel, airline or car rental company. For further information, check out our Customer Service Portal. We’ll help you every step of the way.

Discover the most popular places to visit in Headingley

Image for Red River Exhibition Park

Red River Exhibition Park

4.5/5(5 reviews)

Learn about the local history of Headingley with a stop at Red River Exhibition Park. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Red River Exhibition Park
Image for BellMTS Iceplex

BellMTS Iceplex

4.5/5(2 reviews)

You can take time to visit BellMTS Iceplex during your travels to Headingley. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

BellMTS Iceplex
Image for John Blumberg Golf Course

John Blumberg Golf Course

5/5(1 review)

Enjoy a round of golf in Headingley at John Blumberg Golf Course. Experience the area's fascinating museums or attend a sporting event.

John Blumberg Golf Course

Other vacations you might like

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