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
Jul. 28 - Jul. 30
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Winnipeg (YWG)
8.4/10 Very Good! (1,411 reviews)
We loved the laid back relaxing rooms, and the pool but could barely swim due to pushy people/kids, would definitely recommend supervision in the pool area.

Reviewed on Jun. 17, 2024

Canad Inns Destination Centre Brandon

Canad Inns Destination Centre Brandon

3.5 out of 5
per person
Aug. 8 - Aug. 15
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Winnipeg (YWG)
8.6/10 Excellent! (758 reviews)
Staff are always friendly. Rooms are very clean. I always ask for upper floors away from the pool area for quiet. Lower floors can be a little noisier due to families enjoying the large water slide and pool area which is a great size for a getaway.

Reviewed on Jun. 11, 2024

Humphry Inn & Suites

Humphry Inn & Suites

2.5 out of 5
Downtown Winnipeg
per person
Jul. 28 - Jul. 30
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Winnipeg (YWG)
8.4/10 Very Good! (1,003 reviews)
Very walkable to Forks, Human Rights Museum, Ballpark. Bed was very comfortable, room clean, staff friendly, enjoyed the breakfast provided. Enjoyed Music event at Bluenote park just down the street! Would stay again as convenient and comfortable. Surrounding area was clean and felt safe.

Reviewed on Jun. 17, 2024

Canad Inns Destination Centre Fort Garry

Canad Inns Destination Centre Fort Garry

3 out of 5
Fort Garry
per person
Aug. 30 - Sep. 1
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Winnipeg (YWG)
8/10 Very Good! (1,000 reviews)
Our room was a theme room, it was very nice and bed very comfortable. Loved the jet tub shaped like a boat. The only problem was our room was directly across from elevator and could hear it open and close with every guest entering or exiting. We didn't have enough time to try out the pool/ waterslide area.We also missed breakfast because bed was too comfortable 😴 😉 to get out of. Staff was friendly. Room was clean. Wish the room had a balcony.

Reviewed on Jun. 14, 2024

Canad Inns Destination Centre Club Regent Casino Hotel

Canad Inns Destination Centre Club Regent Casino Hotel

3 out of 5
Transcona
per person
Jul. 28 - Jul. 30
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Winnipeg (YWG)
9/10 Wonderful! (1,000 reviews)
It was exactly what I needed before my trip home - a quiet place and nice bed to sleep in ❤️

Reviewed on Jun. 16, 2024

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 $140 per night from Jul. 7 to Jul. 8
CA $140
CA $157 total
includes taxes & fees
Jul 7 - Jul 8
8.8/10 Excellent! (1,003 reviews)
"Blinds need to be updated, they don't block light at all if you are planning on napping during day."

Reviewed on Jun. 15, 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 $164 per night from Jul. 2 to Jul. 3
CA $164
CA $183 total
includes taxes & fees
Jul 2 - Jul 3
8.6/10 Excellent! (1,001 reviews)
"Great facilities for families with pool and water slides."

Reviewed on Jun. 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 $193 per night from Jun. 23 to Jun. 24
CA $193
CA $228 total
includes taxes & fees
Jun 23 - Jun 24
8.4/10 Very Good! (1,419 reviews)
"Great service"

Reviewed on Jun. 16, 2024

Victoria Inn Hotel and Convention Centre Winnipeg
See all 501 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?
Our Headingley packages, which begin at just CA $418, 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 Softball Complex

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

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.