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.
Sandman Signature Winnipeg Airport Hotel & Suites
St. James
Price was CA $672, price is now CA $531 per person
CA $531
per person
Jun 16 - Jun 18
found 4 hours ago
Roundtrip flight included
Hamilton (YHM) to Winnipeg (YWG)
9.2/10 Wonderful! (390 reviews)
Clean, quiet, well kept hotel. Will book again.
Reviewed on May 1, 2026
Canad Inns Destination Centre Fort Garry
Fort Garry
Price was CA $765, price is now CA $622 per person
CA $622
per person
Jul 17 - Jul 20
found 11 hours ago
Roundtrip flight included
Vancouver (YVR) to Winnipeg (YWG)
8/10 Very Good! (1,292 reviews)
The staff was so friendly and helpful
Reviewed on May 10, 2026
Canad Inns Destination Centre Club Regent Casino Hotel
Transcona
Price was CA $716, price is now CA $592 per person
CA $592
per person
Jul 25 - Jul 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Winnipeg (YWG)
9/10 Wonderful! (1,636 reviews)
Everything was great - the staff, restaurant, parking, room etc but we were located just off the elevator foyer and the ice machine-beverage machine had a very loud hum that was a little annoying, and the heater in the room was noisy :), but overall, it was a great stay and will again.
Reviewed on May 8, 2026
Canad Inns Destination Centre Transcona
Transcona
Price was CA $685, price is now CA $569 per person
CA $569
per person
Jul 25 - Jul 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Winnipeg (YWG)
8.4/10 Very Good! (1,005 reviews)
Arm wasn’t working you to level your curtain so the heat can come in, my room was cold throughout the night I had to keep window curtain open so I can feel some heat
Reviewed on May 10, 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 May 17 to May 18
CA $130
CA $146 total
May 17 - May 18
includes taxes & fees
9/10 Wonderful! (1,477 reviews)
room above us kept us up all night with jumping and yelling
Reviewed on May 10, 2026
Best Western Plus Winnipeg West
4140 Portage Avenue Headingley MB
Fully refundableReserve now, pay when you stay
The price is CA $195 per night from May 19 to May 20
CA $195
CA $219 total
May 19 - May 20
includes taxes & fees
9/10 Wonderful! (1,006 reviews)
A good place to stay.
Reviewed on May 9, 2026
Victoria Inn Hotel and Convention Centre Winnipeg
1808 Wellington Ave Winnipeg MB
Fully refundableReserve now, pay when you stay
The price is CA $195 per night from May 19 to May 20
CA $195
CA $230 total
May 19 - May 20
includes taxes & fees
8.4/10 Very Good! (3,034 reviews)
Breakfast was fast service friendly. Beds were.comfy
Reviewed on May 10, 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.
