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
Fort Garry
Price was CA $841, price is now CA $655 per person
CA $655
per person
Jul 19 - Jul 23
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
8/10 Very Good! (1,263 reviews)
For the price, it was a lovely stay, clean, quiet and nice to have some restaurant and pub on site. But no HD TV ? In 2026? Poor especially when it was the first round of the NHL playoffs and every night we were too tired to go to the tavern..
Reviewed on Apr 23, 2026
Canad Inns Destination Centre Transcona
Transcona
Price was CA $936, price is now CA $699 per person
CA $699
per person
Jun 7 - Jun 11
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
8.4/10 Very Good! (1,006 reviews)
Everything was great except for the Aaltos breakfast buffet, the scrambled eggs tasted awful and not much choice with food.
Reviewed on Apr 20, 2026
The Fairmont Winnipeg Gold Experience
Exchange District
Price was CA $1,461, price is now CA $1,113 per person
CA $1,113
per person
Jun 7 - Jun 11
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
8.4/10 Very Good! (34 reviews)
We love this hotel! It feels smaller and very service oriented. The staff were amazing!
The Gold service was absolutely excellent with a wonderful breakfast each day and friendly and professional Concierge.
The location of the Fairmont Winnipeg is also perfect for all sorts of walking or exploring cafes, bars and restaurants in the Exchange District. Love it!
Reviewed on Apr 23, 2026
Headingley Hotel Deals
Motel 6 Headingley, MB - Winnipeg West
4400 Portage Avenue Headingley MB
Fully refundableReserve now, pay when you stay
The price is CA $125 per night from May 3 to May 4
CA $125
CA $140 total
May 3 - May 4
includes taxes & fees
9.2/10 Wonderful! (1,447 reviews)
Heater/air conditioner took a bit to set properly at first, but was good after a couple of days.
Reviewed on Apr 24, 2026
Best Western Plus Winnipeg West
4140 Portage Avenue Headingley MB
Fully refundableReserve now, pay when you stay
The price is CA $198 per night from Apr 28 to Apr 29
CA $198
CA $222 total
Apr 28 - Apr 29
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
The hotel was clean, the rooms need more convenient options to plug devices in. Our stay was great, except for the part where we were woken up in the middle of the night from people yelling and fighting. Other than that, the hotel was decent.
Reviewed on Apr 24, 2026
Victoria Inn Hotel and Convention Centre Winnipeg
1808 Wellington Ave Winnipeg MB
Fully refundableReserve now, pay when you stay
The price is CA $169 per night from May 24 to May 25
CA $169
CA $200 total
May 24 - May 25
includes taxes & fees
8.4/10 Very Good! (2,982 reviews)
Easy parking pool and hot tub were great
Reviewed on Apr 24, 2026
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.
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.
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.
Explore a world of travel with Expedia
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- Assiniboia Downs
- Assiniboine Park
- Assiniboine Park Zoo
- Beaudry Provincial Park
- Bristol Aerospace Limited
- Brooklands Vacations
- Canadian Forces Base Winnipeg
- Corydon Avenue
- Fortwhyte Alive Center
- Glendale Golf and Country Club
- Grant Park Shopping Centre
- Grant's Old Mill Museum
- John Blumberg Softball Complex
- Kid City
- Leo Mol Sculputure Garden
- Little Mountain Park
- Mcphillips Station Casino
- Polo Park
- Prairie Dog Central Railway
- Red River College
- Red River Exhibition Park
- Saint Francois Xavier Vacations
- Speedworld Indoor Kart Track
- The Players Course
- Thunder Rapids Fun Park
- Tuxedo Vacations
- U-Puttz Thrill Zone
- Unicity Mall
- University of Winnipeg
- Visit Birchwood
- Visit Westdale
- Winnipeg Vacations
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
