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 $832, price is now CA $595 per person
CA $595
per person
Apr 22 - Apr 27
found 21 hours ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
8.4/10 Very Good! (1,001 reviews)
Nice clean and comfortable room. Appreciated having a good restaurant in house.
Reviewed on Feb 5, 2026
Humphry Inn & Suites
Downtown Winnipeg
Price was CA $903, price is now CA $628 per person
CA $628
per person
Apr 22 - Apr 27
found 21 hours ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
8.2/10 Very Good! (1,479 reviews)
Our room was even nicer than pictured. Spacious and comfortable, clean and everything we needed. Great free breakfast. Really welcoming staff at front desk, breakfast bar and housekeeping. Would definitely stay here again
Reviewed on Feb 7, 2026
Canad Inns Destination Centre Fort Garry
Fort Garry
Price was CA $826, price is now CA $598 per person
CA $598
per person
Apr 22 - Apr 27
found 21 hours ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
8/10 Very Good! (1,105 reviews)
The front staff person upgraded us to one of the newly renovated suites. The room was fantastic. The rest of the staff were excellent and went out of there way to help us whenever we needed it.
Reviewed on Feb 4, 2026
The Fairmont Winnipeg Gold Experience
Exchange District
Price was CA $2,134, price is now CA $1,559 per person
CA $1,559
per person
Apr 22 - Apr 27
found 21 hours ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
8.6/10 Excellent! (30 reviews)
Enjoyed the Fairmont Gold Experience. Gold Lounge was closed for renovations on our last day, but the hotel took great care of us in the restaurant for breakfast. We will be back.
Reviewed on Feb 5, 2025
The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel
Downtown Winnipeg
Price was CA $964, price is now CA $724 per person
CA $724
per person
Apr 22 - Apr 27
found 21 hours ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
9.2/10 Wonderful! (1,001 reviews)
8th floor was a treat,
Great view
Nice bed
Reviewed on Feb 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 $120 per night from Mar 1 to Mar 2
CA $120
CA $134 total
Mar 1 - Mar 2
includes taxes & fees
9/10 Wonderful! (1,352 reviews)
Clean and bright environment. Check in desk was staffed by pleasant people, made settling in easy. The only complaint i have is there isn't enough parking with plug-ins....and it is Winterpeg. I will be checking in again
Reviewed on Feb 3, 2026
Best Western Plus Winnipeg West
4140 Portage Avenue Headingley MB
Fully refundableReserve now, pay when you stay
The price is CA $175 per night from Feb 22 to Feb 23
CA $175
CA $196 total
Feb 22 - Feb 23
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
Nice
Reviewed on Feb 3, 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 Feb 22 to Feb 23
CA $179
CA $212 total
Feb 22 - Feb 23
includes taxes & fees
8.4/10 Very Good! (2,790 reviews)
Convenient location. Well-maintained room & facilities.
Reviewed on Feb 3, 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.
