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.
Humphry Inn & Suites
Downtown Winnipeg
Price was CA $436, price is now CA $348 per person
CA $348
per person
Sep 11 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Winnipeg (YWG)
8.4/10 Very good! (1,641 reviews)
Fantastic location for downtown Winnipeg and The Forks area. On site parking was a big bonus. The room had an odd smell on first entrance but 20 minutes or so of air conditioning cleared the air. Comfortable beds (compared with the Days Inns and Wingates to follow). Breakfast was "no frills" but quite adequate. If I return to Winnipeg, the Humphry will likely be my hotel of choice.
Reviewed on Jun 25, 2026
Days Inn & Suites by Wyndham Winnipeg Airport Manitoba
St. James
Price was CA $1,182, price is now CA $966 per person
CA $966
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Winnipeg (YWG)
7.8/10 Good! (1,485 reviews)
There was too much noise at 1:30 am.
Reviewed on Jun 26, 2026
Victoria Inn Hotel & Convention Centre Brandon
Price was CA $818, price is now CA $669 per person
CA $669
per person
Aug 13 - Aug 18
found 23 hours ago
Roundtrip flight included
Toronto (YYZ) to Winnipeg (YWG)
8.6/10 Excellent! (1,009 reviews)
Have stayed many times and have enjoyed it overall....this time however, we noticed an upswing in homeless people hanging around....and although I don't have any damning evidence, our vehicle was broken into and items stolen from it.....the perpetrator's we professionals....leaving only a muddy footprint inside the vehicle....not everything was stolen....basically some new clothing that we had purchased....and a brush out of the glove compartment......
Reviewed on Jun 25, 2026
Sandman Hotel & Suites Winnipeg Airport
St. James
Price was CA $966, price is now CA $794 per person
CA $794
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Winnipeg (YWG)
8.2/10 Very good! (1,728 reviews)
Room was clean and they only charged $50 for security deposit.
Reviewed on Jun 22, 2026
Canad Inns Destination Centre Portage la Prairie
Price was CA $672, price is now CA $556 per person
CA $556
per person
Aug 13 - Aug 18
found 23 hours ago
Roundtrip flight included
Toronto (YYZ) to Winnipeg (YWG)
8/10 Very good! (984 reviews)
Everything you need in one location. Bar, pool, restaurant.
Reviewed on Jun 6, 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 $150 per night from Jun 28 to Jun 29
CA $150
CA $168 total
Jun 28 - Jun 29
includes taxes & fees
9/10 Wonderful! (1,553 reviews)
"Was good , Dog park awesome idea 4 towels great ! Bed sheets very nice . Beds to soft didnt sleep well"
Reviewed on Jun 26, 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 Jun 28 to Jun 29
CA $184
CA $206 total
Jun 28 - Jun 29
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
"Nice hotel"
Reviewed on Jun 23, 2026
The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel
222 Broadway Winnipeg MB
Fully refundable
The price is CA $180 per night from Jun 30 to Jul 1
CA $180
CA $212 total
Jun 30 - Jul 1
includes taxes & fees
9.2/10 Wonderful! (1,197 reviews)
"Beautiful ambiance and great service. Perfect place for a solo getaway. The food is always divine."
Reviewed on Jun 27, 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.
Stay near popular Headingley attractions
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- Masonic Temple
- Unicity Mall
- Assiniboine Park Zoo
- Prairie Dog Central Railway
- Manitoba Children's Museum
- Rbc Convention Centre Winnipeg
- Polo Park
- Little Mountain Park
- Celebrations Dinner Theatre
- Grant Park Shopping Centre
- Canadian Museum for Human Rights
- Burton Cummings Theatre
- Leo Mol Sculputure Garden
- Kid City
- Red River Exhibition Park
- Visit Downtown Winnipeg
- Beaudry Provincial Park
- Canadian Forces Base Winnipeg
- John Blumberg Softball Complex
- Tinkertown
- Grant's Old Mill Museum
- Tuxedo Vacations
- Kildonan Park
- Fortwhyte Alive Center
- Thunder Rapids Fun Park
- Speedworld Indoor Kart Track
- Assiniboine Park
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- Mcphillips Station Casino
- Corydon Avenue
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
