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.
Travelodge by Wyndham Winnipeg East
St. Vital
Price was CA $646, price is now CA $545 per person
CA $545
per person
Jul 16 - Jul 20
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Winnipeg (YWG)
8.2/10 Very Good! (1,781 reviews)
Our room was an older dated room. It was ok but could hear the pool noise and hallway noise. Could use some updating as it would make it more desirable.
Reviewed on Jun 13, 2026
Sandman Signature Winnipeg Airport Hotel & Suites
St. James
Price was CA $790, price is now CA $669 per person
CA $669
per person
Jul 24 - Jul 26
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Winnipeg (YWG)
9.2/10 Wonderful! (421 reviews)
The people working the front desk were considerate, kind and professional. The room was very clean and comfortable. Decor was snazzy. Would 100% stay again.
Reviewed on Jun 12, 2026
Canad Inns Destination Centre Fort Garry
Fort Garry
Price was CA $828, price is now CA $709 per person
CA $709
per person
Sep 7 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Winnipeg (YWG)
8/10 Very Good! (1,328 reviews)
We enjoyed our stay at this very nice hotel.
Reviewed on Jun 12, 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 $147 per night from Jun 28 to Jun 29
CA $147
CA $165 total
Jun 28 - Jun 29
includes taxes & fees
9.2/10 Wonderful! (1,539 reviews)
"Y"
Reviewed on Jun 12, 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 Jun 14 to Jun 15
CA $184
CA $206 total
Jun 14 - Jun 15
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
"Great"
Reviewed on May 25, 2026
Victoria Inn Hotel and Convention Centre Winnipeg
1808 Wellington Ave Winnipeg MB
Fully refundableReserve now, pay when you stay
The price is CA $199 per night from Jul 1 to Jul 2
CA $199
CA $235 total
Jul 1 - Jul 2
includes taxes & fees
8.4/10 Very Good! (3,093 reviews)
"Staff was very good and especially the Shuttle service drivers are very courteous and helpful."
Reviewed on Jun 12, 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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- 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.
