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 $1,341, price is now CA $990 per person
CA $990
per person
May 16 - May 23
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Winnipeg (YWG)
8/10 Very Good! (1,208 reviews)
Clean room, was able to enjoy myself in my room without any complaint other than a drunk couple fighting after midnight with her boyfriend Pounding on there hotel room door. Pool she definitely be open to adults till 11 pm as well
Reviewed on Mar 9, 2026
Canad Inns Destination Centre Portage la Prairie
Price was CA $1,085, price is now CA $877 per person
CA $877
per person
May 16 - May 23
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Winnipeg (YWG)
8/10 Very Good! (942 reviews)
The pool was what we were more interested in, pool was warm and mostly clean, the kiddie pool had quite a bit of little dirt in it. When we checked in the staff member actually was pretty rude, he was not pleasant to deal with at all. And we booked a suite room for 4 of us, with the pull out couch as a bed and there was no sheets in the pull out couch. My husband had to ask for a set at the counter and the gentlemen at the desk was a bit rude. But the room was overall clean.
Reviewed on Mar 3, 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 $120 per night from Mar 16 to Mar 17
CA $120
CA $134 total
Mar 16 - Mar 17
includes taxes & fees
9.2/10 Wonderful! (1,392 reviews)
They are okay, no issues
Reviewed on Mar 9, 2026
Best Western Plus Winnipeg West
4140 Portage Avenue Headingley MB
The price is CA $184 per night from Mar 25 to Mar 26
CA $184
CA $206 total
Mar 25 - Mar 26
includes taxes & fees
9/10 Wonderful! (1,007 reviews)
Easy access for a late might stop. Friendly staff, nice room and a decent breakfast.
Reviewed on Mar 8, 2026
Victoria Inn Hotel and Convention Centre Winnipeg
1808 Wellington Ave Winnipeg MB
Fully refundableReserve now, pay when you stay
The price is CA $179 per night from Mar 12 to Mar 13
CA $179
CA $212 total
Mar 12 - Mar 13
includes taxes & fees
8.4/10 Very Good! (2,855 reviews)
Just needs a shower in the pool area unless I missed it. Overall, it was okay however, there were children knocking on room doors and running off. Thanks to front desk for responding to this.
Reviewed on Mar 11, 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
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.
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.
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.
