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 Club Regent Casino Hotel
Transcona
Price was CA $980, price is now CA $733 per person
CA $733
per person
May 19 - May 24
found 1 day ago
Roundtrip non-stop flight included
Comox (YQQ) to Winnipeg (YWG)
9/10 Wonderful! (1,619 reviews)
Breakfast was good great deal
Price for the week day room was great parking there was a lot of space
Reviewed on Apr 14, 2026
Sandman Signature Winnipeg Airport Hotel & Suites
St. James
Price was CA $1,557, price is now CA $1,097 per person
CA $1,097
per person
May 19 - May 24
found 1 day ago
Roundtrip non-stop flight included
Comox (YQQ) to Winnipeg (YWG)
9.2/10 Wonderful! (374 reviews)
Nice clean will return
Reviewed on Apr 13, 2026
Humphry Inn & Suites
Downtown Winnipeg
Price was CA $1,131, price is now CA $811 per person
CA $811
per person
May 19 - May 24
found 1 day ago
Roundtrip non-stop flight included
Comox (YQQ) to Winnipeg (YWG)
8.4/10 Very Good! (1,578 reviews)
The check-in was easy with friendly staff. The parking area was tight, but we made it work. Great breakfast in the morning. Would definitely stay here again.
Reviewed on Apr 17, 2026
Canad Inns Destination Centre Fort Garry
Fort Garry
Price was CA $998, price is now CA $742 per person
CA $742
per person
May 19 - May 24
found 1 day ago
Roundtrip non-stop flight included
Comox (YQQ) to Winnipeg (YWG)
8/10 Very Good! (1,257 reviews)
Everything was excellent staff is fast and friendly this is the second time staying there will stay again for sure
Reviewed on Apr 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 $125 per night from May 3 to May 4
CA $125
CA $140 total
May 3 - May 4
includes taxes & fees
9.2/10 Wonderful! (1,437 reviews)
Great price, comfortable and clean room
Reviewed on Apr 16, 2026
Best Western Plus Winnipeg West
4140 Portage Avenue Headingley MB
Fully refundableReserve now, pay when you stay
The price is CA $207 per night from May 10 to May 11
CA $207
CA $232 total
May 10 - May 11
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
Everything was great but the pool was cold Staff was excellent ❤️ Lady at check in was very very friendly
Reviewed on Apr 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 $169 per night from May 3 to May 4
CA $169
CA $200 total
May 3 - May 4
includes taxes & fees
8.4/10 Very Good! (2,967 reviews)
Very nice place to stay; quiet room; comfortable beds; walk-in shower; great restaurant/bar; nice looking pool, but we did not bring bathing suits.
Reviewed on Apr 17, 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.
