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 $642, price is now CA $498 per person
CA $498
per person
Jun 30 - Jul 4
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
8/10 Very Good! (1,004 reviews)
Great service and friendly staff
Reviewed on May 7, 2026
Canad Inns Destination Centre Club Regent Casino Hotel
Transcona
Price was CA $769, price is now CA $572 per person
CA $572
per person
Jun 30 - Jul 4
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
9/10 Wonderful! (1,636 reviews)
Everything was great - the staff, restaurant, parking, room etc but we were located just off the elevator foyer and the ice machine-beverage machine had a very loud hum that was a little annoying, and the heater in the room was noisy :), but overall, it was a great stay and will again.
Reviewed on May 8, 2026
Canad Inns Destination Centre Fort Garry
Fort Garry
Price was CA $746, price is now CA $557 per person
CA $557
per person
Jun 30 - Jul 4
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
8/10 Very Good! (1,292 reviews)
The room was comfortable and spacious. The hotel felt very secure.
Reviewed on May 6, 2026
Canad Inns Destination Centre Transcona
Transcona
Price was CA $776, price is now CA $606 per person
CA $606
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Winnipeg (YWG)
8.4/10 Very Good! (1,005 reviews)
Room was clean, staff was friendly and helpfull
Reviewed on May 7, 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 $130 per night from May 10 to May 11
CA $130
CA $146 total
May 10 - May 11
includes taxes & fees
9/10 Wonderful! (1,473 reviews)
Good
Reviewed on May 7, 2026
Best Western Plus Winnipeg West
4140 Portage Avenue Headingley MB
Fully refundableReserve now, pay when you stay
The price is CA $195 per night from May 19 to May 20
CA $195
CA $219 total
May 19 - May 20
includes taxes & fees
9/10 Wonderful! (1,003 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 $195 per night from May 9 to May 10
CA $195
CA $230 total
May 9 - May 10
includes taxes & fees
8.4/10 Very Good! (3,027 reviews)
Staff were very helpful. TV could have a CBC station
Reviewed on May 6, 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.
