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.
Victoria Inn Hotel and Convention Centre Winnipeg
St. James
Price was CA $593, price is now CA $444 per person
CA $444
per person
May 15 - May 18
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Winnipeg (YWG)
8.4/10 Very Good! (2,464 reviews)
Clean room and staff very friendly
Reviewed on Mar 1, 2026
The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel
Downtown Winnipeg
Price was CA $1,026, price is now CA $812 per person
CA $812
per person
May 6 - May 10
found 2 days ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
9.2/10 Wonderful! (1,001 reviews)
Everything was good! SUPER quiet for sleeping.
Reviewed on Mar 1, 2026
The Fairmont Winnipeg Gold Experience
Exchange District
Price was CA $1,608, price is now CA $1,283 per person
CA $1,283
per person
May 6 - May 10
found 2 days ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
8.6/10 Excellent! (30 reviews)
Enjoyed the Fairmont Gold Experience. Gold Lounge was closed for renovations on our last day, but the hotel took great care of us in the restaurant for breakfast. We will be back.
Reviewed on Feb 5, 2025
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 8 to Mar 9
CA $120
CA $134 total
Mar 8 - Mar 9
includes taxes & fees
9.2/10 Wonderful! (1,379 reviews)
Nice stay staff friendly
Reviewed on Mar 1, 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 15 to Mar 16
CA $184
CA $206 total
Mar 15 - Mar 16
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
Yes there good
Reviewed on Feb 26, 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 Apr 1 to Apr 2
CA $185
CA $219 total
Apr 1 - Apr 2
includes taxes & fees
8.4/10 Very Good! (2,829 reviews)
Clean room and staff very friendly
Reviewed on Mar 1, 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
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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.
