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 Fort Garry
Fort Garry
Price was CA $791, price is now CA $603 per person
CA $603
per person
May 15 - May 18
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Winnipeg (YWG)
8/10 Very Good! (1,231 reviews)
Enjoyed a family get together on Easter Sunday with all the amenities that were offered. Including the pool area, pet friendly room and nice buffet dinner reservation. Thank you!
Reviewed on Apr 6, 2026
Victoria Inn Hotel and Convention Centre Winnipeg
St. James
Price was CA $842, price is now CA $646 per person
CA $646
per person
May 15 - May 18
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Winnipeg (YWG)
8.4/10 Very Good! (2,923 reviews)
The rooms and surrounding hotel are very clean, noise levels are down after 11pm. VLT Lounge an asset for entertainment, the food is also well prepared.
Reviewed on Apr 7, 2026
Sandman Hotel & Suites Winnipeg Airport
St. James
Price was CA $852, price is now CA $673 per person
CA $673
per person
May 15 - May 18
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Winnipeg (YWG)
8.2/10 Very Good! (1,641 reviews)
The bath tub drain was half blocked otherwise clean and fresh
Reviewed on Apr 8, 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 $125 per night from Apr 19 to Apr 20
CA $125
CA $140 total
Apr 19 - Apr 20
includes taxes & fees
9.2/10 Wonderful! (1,422 reviews)
It was a good stay
Reviewed on Apr 7, 2026
Best Western Plus Winnipeg West
4140 Portage Avenue Headingley MB
Fully refundableReserve now, pay when you stay
The price is CA $216 per night from Apr 26 to Apr 27
CA $216
CA $242 total
Apr 26 - Apr 27
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
Very clean and spacious room. Totally recommend.
Reviewed on Apr 5, 2026
Victoria Inn Hotel and Convention Centre Winnipeg
1808 Wellington Ave Winnipeg MB
Fully refundableReserve now, pay when you stay
The price is CA $229 per night from May 3 to May 4
CA $229
CA $271 total
May 3 - May 4
includes taxes & fees
8.4/10 Very Good! (2,937 reviews)
It was great
Reviewed on Apr 7, 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.
