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 $594, price is now CA $493 per person
CA $493
per person
Apr 27 - Apr 30
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Winnipeg (YWG)
8/10 Very Good! (1,218 reviews)
Confusing layout, felt like an indoor motel but the staff were amazing. The beds were not very comfortable but they did the trick.
Reviewed on Mar 13, 2026
Canad Inns Destination Centre Club Regent Casino Hotel
Transcona
Price was CA $749, price is now CA $593 per person
CA $593
per person
May 28 - May 31
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Winnipeg (YWG)
9/10 Wonderful! (1,587 reviews)
It was nice, the staff were very helpful and friendly.
I will definitely be back.
Reviewed on Mar 11, 2026
Victoria Inn Hotel and Convention Centre Winnipeg
St. James
Price was CA $744, price is now CA $597 per person
CA $597
per person
Apr 27 - Apr 30
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Winnipeg (YWG)
8.4/10 Very Good! (2,863 reviews)
Great we love coming here and the pool. I was just disappointed I asked a lady at the front desk to get our room vacuumed and it was never done. 5/5 either way.
Reviewed on Mar 16, 2026
Sandman Hotel & Suites Winnipeg Airport
St. James
Price was CA $727, price is now CA $604 per person
CA $604
per person
Apr 27 - Apr 30
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Winnipeg (YWG)
8.2/10 Very Good! (1,613 reviews)
I was only there for 1 night and to sleep, as I was travelling through.
Reviewed on Mar 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 $130 per night from Mar 22 to Mar 23
CA $130
CA $146 total
Mar 22 - Mar 23
includes taxes & fees
9.2/10 Wonderful! (1,395 reviews)
Easy access
Reviewed on Mar 15, 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 Apr 5 to Apr 6
CA $184
CA $206 total
Apr 5 - Apr 6
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
Value for money. Clean, and friendly staff. We’ve come for the pool and the hot tub, and the kids enjoyed them. Breakfast is a big bonus. Good food! Highly recommended for a weekend family getaway.
Reviewed on Mar 15, 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 17 to Mar 18
CA $179
CA $212 total
Mar 17 - Mar 18
includes taxes & fees
8.4/10 Very Good! (2,873 reviews)
Great we love coming here and the pool. I was just disappointed I asked a lady at the front desk to get our room vacuumed and it was never done. 5/5 either way.
Reviewed on Mar 16, 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.
