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 Transcona
Transcona
Price was CA $687, price is now CA $506 per person
CA $506
per person
May 6 - May 10
found 19 hours ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
8.4/10 Very Good! (1,001 reviews)
We were pleased with our stay overall. The room was very clean and we enjoyed all of the local photography prints on the walls. The staff were all helpful and courteous and we enjoyed the pool and the hot tub.
Reviewed on Feb 23, 2026
Humphry Inn & Suites
Downtown Winnipeg
Price was CA $760, price is now CA $543 per person
CA $543
per person
May 6 - May 10
found 19 hours ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
8.2/10 Very Good! (1,479 reviews)
Nice clean, comfy bed and good coices at breakfast. I would stay here again.
Reviewed on Feb 26, 2026
Comfort Inn South
Fort Garry
Price was CA $772, price is now CA $560 per person
CA $560
per person
Apr 2 - Apr 5
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YTO) to Winnipeg (YWG)
8.6/10 Excellent! (1,029 reviews)
My review is based on this hotel being one of the more inexpensive ones online.
Based on some other reviews, I was hesitant but tried it anyways for 3 nights.
The room was clean and acceptable. They did come and tidy the room up everyday.
The breakfast was fantastic. It was the usual offerings and it didn't disappoint.
The staff was wonderful.
I've been in some questionable hotels (the grandkids won't let me pick the hotels anymore) but this one I was on my own, and it didn't disappoint me.
Reviewed on Feb 26, 2026
Canad Inns Destination Centre Garden City
Leila-McPhillips Triangle
Price was CA $670, price is now CA $511 per person
CA $511
per person
May 6 - May 10
found 19 hours ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
8/10 Very Good! (1,001 reviews)
Clean and quiet room, however bathroom supplies like shower gel seems very "watery" (diluted?).
Also empty mini bar, no soda or snacks for instance... Those things are very appreciated after a long day of travel. Good staff!
Reviewed on Feb 24, 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 1 to Mar 2
CA $120
CA $134 total
Mar 1 - Mar 2
includes taxes & fees
9.2/10 Wonderful! (1,374 reviews)
Shower head had very little pressure. Bathroom fan sounded like a helicopter (luckily we were on 3rd floor and no room above). Room curtain didn’t go all the way, so lots of light from parking lot. Noise complaints after 11:00 pm on 3rd floor, and someone knocked on our room door at 1:06 am and continued ...
Reviewed on Feb 23, 2026
Best Western Plus Winnipeg West
4140 Portage Avenue Headingley MB
Fully refundableReserve now, pay when you stay
The price is CA $184 per night from Mar 12 to Mar 13
CA $184
CA $206 total
Mar 12 - Mar 13
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
Yes there good
Reviewed on Feb 26, 2026
Victoria Inn Hotel and Convention Centre Winnipeg
1808 Wellington Ave Winnipeg MB
Fully refundableReserve now, pay when you stay
The price is CA $207 per night from Mar 6 to Mar 7
CA $207
CA $245 total
Mar 6 - Mar 7
includes taxes & fees
8.4/10 Very Good! (2,821 reviews)
Staff and room
Reviewed on Feb 25, 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.
