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 Garden City
Leila-McPhillips Triangle
Price was CA $516, price is now CA $407 per person
CA $407
per person
Apr 30 - May 4
found 17 hours ago
Roundtrip flight included
Vancouver (YVR) to Winnipeg (YWG)
8/10 Very Good! (1,001 reviews)
Room was in good condition, amenities fine !! The mattress was very poor !! Dipped badly!! The room temperature was way to hot even with thermostat adjusted, the fan on AC unit was extremely loud and did not cool room off
Reviewed on Feb 15, 2026
Humphry Inn & Suites
Downtown Winnipeg
Price was CA $723, price is now CA $534 per person
CA $534
per person
Apr 30 - May 4
found 17 hours ago
Roundtrip flight included
Vancouver (YVR) to Winnipeg (YWG)
8.2/10 Very Good! (1,479 reviews)
Everything was great, the breakfast was delicious. Will come again
Reviewed on Feb 16, 2026
Canad Inns Destination Centre Club Regent Casino Hotel
Transcona
Price was CA $696, price is now CA $524 per person
CA $524
per person
Apr 30 - May 4
found 17 hours ago
Roundtrip flight included
Vancouver (YVR) to Winnipeg (YWG)
9/10 Wonderful! (1,380 reviews)
Room was spotless clean but heating was noisy
Staff was courteous but when requested for late checkout was told that we have to request at 7 am to morning staff on 1 st come basis
Idea of late checkout to sleep till late after spending night at casinos till 5 am
Reviewed on Feb 16, 2026
Victoria Inn Hotel and Convention Centre Winnipeg
St. James
Price was CA $675, price is now CA $510 per person
CA $510
per person
Apr 30 - May 4
found 17 hours ago
Roundtrip flight included
Vancouver (YVR) to Winnipeg (YWG)
8.4/10 Very Good! (2,464 reviews)
Everything was great expect the service I received at the restaurant. Staff were rude that worked at the bar and seemed irritated when I would ask simple questions.
Reviewed on Feb 15, 2026
Canad Inns Destination Centre Fort Garry
Fort Garry
Price was CA $657, price is now CA $498 per person
CA $498
per person
Apr 30 - May 4
found 17 hours ago
Roundtrip flight included
Vancouver (YVR) to Winnipeg (YWG)
8/10 Very Good! (1,105 reviews)
Room was great! Better than expected. Staff was nice. Unfortunately there was two fights in the hall about 2am and some guy coughing and spitting on the floor around 3.
Reviewed on Feb 15, 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 2 to Mar 3
CA $120
CA $134 total
Mar 2 - Mar 3
includes taxes & fees
9/10 Wonderful! (1,366 reviews)
Had a great stay. A little loud with the hockey team staying above us.
Reviewed on Feb 13, 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 2 to Mar 3
CA $184
CA $206 total
Mar 2 - Mar 3
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
Very friendly front desk upon arrival
Reviewed on Feb 13, 2026
Lakeview Signature, Trademark Collection by Wyndham
1999 Wellington Ave Winnipeg MB
Fully refundableReserve now, pay when you stay
The price is CA $161 per night from Feb 20 to Feb 21
CA $161
CA $190 total
Feb 20 - Feb 21
includes taxes & fees
8.8/10 Excellent! (2,588 reviews)
Clean room , friendly staff, easy check in and check out!
Reviewed on Feb 15, 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.
