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 $572, price is now CA $403 per person
CA $403
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Winnipeg (YWG)
8/10 Very Good! (1,231 reviews)
This hotel is clean and very well maintained. A nice restaurant that has lots of food options. The staff is super nice and friendly. We really enjoyed our stay. The price is very affordable, I will definitely be back.
Reviewed on Apr 18, 2026
Humphry Inn & Suites
Downtown Winnipeg
Price was CA $690, price is now CA $493 per person
CA $493
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Vancouver (YVR) 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 Transcona
Transcona
Price was CA $711, price is now CA $512 per person
CA $512
per person
Jun 8 - Jun 11
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Winnipeg (YWG)
8.4/10 Very Good! (1,013 reviews)
Breakfast was great to much food!
Room was clean
Didnt use the pool facilities.
Its unfortunate Altos was closed at supper time but Dinner at the Taven was good
Reviewed on Apr 16, 2026
Canad Inns Destination Centre Club Regent Casino Hotel
Transcona
Price was CA $617, price is now CA $456 per person
CA $456
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Vancouver (YVR) 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
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! (1,438 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! (1,002 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 Apr 20 to Apr 21
CA $169
CA $200 total
Apr 20 - Apr 21
includes taxes & fees
8.4/10 Very Good! (2,969 reviews)
When ordering room service make sure to tell them everything you need to enjoy your meal. I ordered a steak and had to cut it with a butter knife which was quite difficult. Soup with a teaspoon. No salt. No pepper. Also, asked for a late checkout. Was not granted. I have stayed in too many hotels ...
Reviewed on Apr 18, 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.
