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 Fort Garry
Fort Garry
Price was CA $593, price is now CA $449 per person
CA $449
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Winnipeg (YWG)
8/10 Very Good! (1,205 reviews)
Clean room, was able to enjoy myself in my room without any complaint other than a drunk couple fighting after midnight with her boyfriend Pounding on there hotel room door. Pool she definitely be open to adults till 11 pm as well
Reviewed on Mar 9, 2026
Sandman Signature Winnipeg Airport Hotel & Suites
St. James
Price was CA $1,084, price is now CA $772 per person
CA $772
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Winnipeg (YWG)
9/10 Wonderful! (325 reviews)
Clean room, comfortable beds, very nice tavern/bar attached to hotel. Food was unreal good
Reviewed on Mar 9, 2026
Humphry Inn & Suites
Downtown Winnipeg
Price was CA $681, price is now CA $497 per person
CA $497
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Winnipeg (YWG)
8.4/10 Very Good! (1,571 reviews)
Very quiet, very friendly staff and an great location.
Reviewed on Mar 5, 2026
Canad Inns Destination Centre Club Regent Casino Hotel
Transcona
Price was CA $636, price is now CA $475 per person
CA $475
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Winnipeg (YWG)
9/10 Wonderful! (1,578 reviews)
Excellent service and room was bright and clean
Reviewed on Mar 4, 2026
Victoria Inn Hotel and Convention Centre Winnipeg
St. James
Price was CA $599, price is now CA $450 per person
CA $450
per person
May 14 - May 17
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Winnipeg (YWG)
8.4/10 Very Good! (2,832 reviews)
Every thing like the service I expect they provide me above my expectations
Reviewed on Mar 9, 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 16 to Mar 17
CA $120
CA $134 total
Mar 16 - Mar 17
includes taxes & fees
9.2/10 Wonderful! (1,391 reviews)
They are okay, no issues
Reviewed on Mar 9, 2026
Best Western Plus Winnipeg West
4140 Portage Avenue Headingley MB
Fully refundableReserve now, pay when you stay
The price is CA $174 per night from Apr 6 to Apr 7
CA $174
CA $195 total
Apr 6 - Apr 7
includes taxes & fees
9/10 Wonderful! (1,007 reviews)
Easy access for a late might stop. Friendly staff, nice room and a decent breakfast.
Reviewed on Mar 8, 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 Mar 10 to Mar 11
CA $179
CA $212 total
Mar 10 - Mar 11
includes taxes & fees
8.4/10 Very Good! (2,858 reviews)
Every thing like the service I expect they provide me above my expectations
Reviewed on Mar 9, 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.
