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
St. James
Price was CA $680, price is now CA $529 per person
CA $529
per person
Jul 9 - Jul 12
found 6 hours ago
Roundtrip flight included
Hamilton (YHM) to Winnipeg (YWG)
8.4/10 Very Good! (2,974 reviews)
Everything here was wonderful for my family and I. The only thing that wasn’t great was banging on a door for 45 minutes at 3 am. When I notified the front desk, the immediately sent up security but my children were already awake for the day due to it. We enjoyed our stay, none the less and my daughter was obsessed with the pool.
Reviewed on May 2, 2026
Canad Inns Destination Centre Fort Garry
Fort Garry
Price was CA $802, price is now CA $602 per person
CA $602
per person
Jun 11 - Jun 15
found 21 hours ago
Roundtrip flight included
Hamilton (YHM) to Winnipeg (YWG)
8/10 Very Good! (1,276 reviews)
The staff are very friendly! Our room was clean!
We enjoy staying there.
Reviewed on Apr 30, 2026
Canad Inns Destination Centre Transcona
Transcona
Price was CA $764, price is now CA $578 per person
CA $578
per person
Jun 11 - Jun 15
found 21 hours ago
Roundtrip flight included
Hamilton (YHM) to Winnipeg (YWG)
8.4/10 Very Good! (1,002 reviews)
The sheets and pillow stunk like bad b.o. They most definitely were not changed.
Reviewed on May 1, 2026
Canad Inns Destination Centre Garden City
Leila-McPhillips Triangle
Price was CA $672, price is now CA $534 per person
CA $534
per person
Jun 11 - Jun 15
found 21 hours ago
Roundtrip flight included
Hamilton (YHM) to Winnipeg (YWG)
8/10 Very Good! (1,006 reviews)
Lovely bath in King suite
Reviewed on May 1, 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! (1,457 reviews)
Every thing possible was properly attended to by the management of this property.
Reviewed on Apr 30, 2026
Best Western Plus Winnipeg West
4140 Portage Avenue Headingley MB
Fully refundableReserve now, pay when you stay
The price is CA $216 per night from May 17 to May 18
CA $216
CA $242 total
May 17 - May 18
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
Breakfast was awesome
Reviewed on Apr 30, 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! (3,007 reviews)
Everything here was wonderful for my family and I. The only thing that wasn’t great was banging on a door for 45 minutes at 3 am. When I notified the front desk, the immediately sent up security but my children were already awake for the day due to it. We enjoyed our stay, none the less and my daughter ...
Reviewed on May 2, 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.
