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 Club Regent Casino Hotel
Transcona
Price was CA $846, price is now CA $700 per person
CA $700
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Montreal Metropolitan Airport (YHU) to Winnipeg (YWG)
9/10 Wonderful! (1,679 reviews)
Room was clean, check in and out easy and quick. Food was good in restaurant.
Reviewed on Jun 29, 2026
Canad Inns Destination Centre Transcona
Transcona
Price was CA $800, price is now CA $682 per person
CA $682
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Montreal Metropolitan Airport (YHU) to Winnipeg (YWG)
8.4/10 Very good! (1,003 reviews)
I stayed here for a solo trip. Check-in and check-out were smooth, but I had to wait for housekeeping to check my room before I could get my deposit refunded. That was a little annoying. The property has a tavern, so be prepared for intoxicated people sharing your floor, however, they were mostly well-behaved during my stay.
Reviewed on Jun 29, 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 $172 per night from Jul 12 to Jul 13
CA $172
CA $193 total
Jul 12 - Jul 13
includes taxes & fees
9/10 Wonderful! (1,556 reviews)
"Nothing special! Dry muffins for breakfast! Keep driving."
Reviewed on Jun 28, 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 Jul 23 to Jul 24
CA $184
CA $206 total
Jul 23 - Jul 24
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
"Always a great place to stay especially if you have kids."
Reviewed on Jun 29, 2026
The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel
222 Broadway Winnipeg MB
Fully refundable
The price is CA $186 per night from Jul 31 to Aug 1
CA $186
CA $220 total
Jul 31 - Aug 1
includes taxes & fees
9.2/10 Wonderful! (1,202 reviews)
"This is the Fort Garry Hotel we’re talking about. It’s the epitome of elegance in Winnipeg. The beds are soft, the water pressure perfect, the rooms spotless. They provide bathrobes and even the bath towels are bigger than at other hotels. I asked for a small refrigerator and one was graciously provided ..."
Reviewed on Jun 29, 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
- Manitoba Vacations
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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.
