Headingley Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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 $878, price is now CA $620 per person
CA $620
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Winnipeg (YWG)
8/10 Very Good! (1,001 reviews)
We were met with great service. Though there was a little mixup when booking through a different booking site, the hotel still honoured our reservation. Room was clean. When we needed help, there was prompt service.
Reviewed on Mar 3, 2026
Humphry Inn & Suites
Downtown Winnipeg
Price was CA $1,019, price is now CA $694 per person
CA $694
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Winnipeg (YWG)
8.4/10 Very Good! (1,567 reviews)
We had to clean the dryer before we could use it. Filter and area around the filter was dirty.
The pool and hot tub have been closed for the past couple of years, other than a bike, the gym equipment was not working and everything we put in the fridge froze!
Amenities are misleading!
Reviewed on Mar 3, 2026
Canad Inns Destination Centre Fort Garry
Fort Garry
Price was CA $1,023, price is now CA $702 per person
CA $702
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Winnipeg (YWG)
8/10 Very Good! (1,205 reviews)
The staff are very professional and helpful.
Reviewed on Mar 2, 2026
Canad Inns Destination Centre Transcona
Transcona
Price was CA $973, price is now CA $671 per person
CA $671
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Winnipeg (YWG)
8.4/10 Very Good! (1,001 reviews)
We were pleased with our stay overall. The room was very clean and we enjoyed all of the local photography prints on the walls. The staff were all helpful and courteous and we enjoyed the pool and the hot tub.
Reviewed on Feb 23, 2026
Canad Inns Destination Centre Club Regent Casino Hotel
Transcona
Price was CA $1,217, price is now CA $872 per person
CA $872
per person
May 18 - May 24
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Winnipeg (YWG)
9/10 Wonderful! (1,380 reviews)
Was great reception and understanding when we needed to make a change.
Reviewed on Mar 2, 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 15 to Mar 16
CA $120
CA $134 total
Mar 15 - Mar 16
includes taxes & fees
9.2/10 Wonderful! (1,382 reviews)
Very nice rooms! Nice kitchen, bed was great. My only critique is there is No Gym!!!
Reviewed on Mar 3, 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 18 to Mar 19
CA $184
CA $206 total
Mar 18 - Mar 19
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
Room was nice, staff were great, the pool was chilly and could of been a degree or two warmer
Reviewed on Mar 4, 2026
Victoria Inn Hotel and Convention Centre Winnipeg
1808 Wellington Ave Winnipeg MB
Fully refundableReserve now, pay when you stay
The price is CA $185 per night from Mar 8 to Mar 9
CA $185
CA $219 total
Mar 8 - Mar 9
includes taxes & fees
8.4/10 Very Good! (2,837 reviews)
Beautiful stay beautiful room lots of space
Reviewed on Mar 4, 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
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.
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.
Explore a world of travel with Expedia
- 3 Star Hotels in Birchwood
- 3 Star Hotels in Glendale
- 4 Star Hotels in Birchwood
- 4 Star Hotels in Buchanan
- Hotels near Academy Lanes West
- Hotels near Assiniboia Downs
- Hotels near Assiniboine Park
- Hotels near Assiniboine Park Zoo
- Hotels near Beaudry Provincial Park
- Hotels near BellMTS Iceplex
- Birchwood Hotels
- Hotels with Wifi in Buchanan
- Hotels with an Indoor Pool in Buchanan
- Hotels near Canadian Forces Base Winnipeg
- Downtown Winnipeg Hotels
- Hotels near Glendale Golf and Country Club
- Hotels near Grant's Old Mill Museum
- Hotels near Historical Museum of St. James - Assiniboia
- Hotels near John Blumberg Golf Course
- Hotels near John Blumberg Softball Complex
- Hotels near Leo Mol Sculputure Garden
- Hotels near Outlet Collection Winnipeg
- Hotels near Polo Park
- Hotels near Red River Exhibition Park
- Hotels near Thunder Rapids Fun Park
- Hotels near Unicity Mall
- Business Hotels in Westdale
- Cheap Hotels in Westdale
- Hotels & Resorts for Couples in Westdale
- Hotels with Free Airport Shuttle in Westdale
- Hotels with an Indoor Pool in Westdale
- Hotels with Waterslides in Westdale
- Lake Hotels in Westdale
- Luxury Hotels in Westdale
- Romantic Hotels in Westdale
- Spa Hotels in Westdale
- Waterpark Hotels in Westdale
- Westdale Hotels
- Cheap Hotels in Winnipeg
- Winnipeg Hotels
- Hotels near Winnipeg James Armstrong Richardson Intl.
- Flights to Winnipeg
- Flights from Winnipeg James Armstrong Richardson Intl.
- Flights from Winnipeg
- Flights from Delhi (DEL) to Winnipeg (YWG)
- Flights from Lagos (LOS) to Winnipeg (YWG)
- Flights from Manila (MNL) to Winnipeg (YWG)
- Flights from Brandon (YBR) to Winnipeg (YWG)
- Flights from Edmonton (YEG) to Winnipeg (YWG)
- Flights from Hamilton (YHM) to Winnipeg (YWG)
- Flights from Halifax (YHZ) to Winnipeg (YWG)
- Flights from Kitchener (YKF) to Winnipeg (YWG)
- Flights from Kelowna (YLW) to Winnipeg (YWG)
- Flights from Ottawa (YOW) to Winnipeg (YWG)
- Flights from Regina (YQR) to Winnipeg (YWG)
- Flights from Thunder Bay (YQT) to Winnipeg (YWG)
- Flights from Montreal (YUL) to Winnipeg (YWG)
- Flights from Vancouver (YVR) to Winnipeg (YWG)
- Flights from Saskatoon (YXE) to Winnipeg (YWG)
- Flights from London (YXU) to Winnipeg (YWG)
- Flights from Abbotsford (YXX) to Winnipeg (YWG)
- Flights from Calgary (YYC) to Winnipeg (YWG)
- Flights from Victoria (YYJ) to Winnipeg (YWG)
- Flights from Toronto (YYZ) to Winnipeg (YWG)
- 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.
