Title: Headingley Vacation Packages & Trips 2025/2026 from CA $452 | Expedia.ca [Headingley Travel Guide](https://expedia.ca/Headingley.dx6145346)[Hotels in Headingley](https://expedia.ca/Headingley-Hotels.d6145346.Travel-Guide-Hotels)[Vacation Rentals in Headingley](https://expedia.ca/Headingley-Vacation-Rentals.d6145346.Travel-Guide-VacationRentals)[Flights to Headingley](https://expedia.ca/Cheap-Flights-To-Headingley.d6145346.Travel-Guide-Flights)[Headingley Car Rentals](https://expedia.ca/Car-Rentals-In-Headingley.d6145346.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Headingley Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings #### 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](https://www.expedia.ca/Assiniboia-Downs-Winnipeg.d6229713.Vacation-Attraction), [BellMTS Iceplex](https://www.expedia.ca/BellMTS-Iceplex-Winnipeg.d553248635026762217.Vacation-Attraction) and [Unicity Mall](https://www.expedia.ca/Unicity-Mall-Winnipeg.d553248621585428171.Vacation-Attraction), 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. ![Victoria Inn Hotel and Convention Centre Winnipeg](https://images.trvl-media.com/lodging/1000000/20000/13300/13226/94dbadb8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Victoria Inn Hotel and Convention Centre Winnipeg St. James CA $452 per person Jan 12 - Jan 16 found 1 day ago Roundtrip flight included Edmonton (YEG) to Winnipeg (YWG) 8.4/10 Very Good! (2,464 reviews) Front desk was pleasant and suggested I take pool wristband, in case I changed my mind (mentioned hot tub, not just a pool). I was travelling for work alone and didn’t pack swimsuit. Noted her kindness and quality service. Room was large, clean and updated. I have stayed here several times. I like the elevator key. Reviewed on Nov 29, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-12/2026-01-16/?FromAirport=YEG&Destination=YWG&NumRoom=1&NumAdult=2&NumChild=0&hotelId=13226&paandie=true&dealMarker=2WmGQimqJPFS2gxWUypPWb9oIRww5MhIBMKOZBLDt8riteiintv5O9Updo0LbLQV) ![Sandman Signature Winnipeg Airport Hotel & Suites](https://images.trvl-media.com/lodging/111000000/110520000/110510700/110510684/e0f50374_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sandman Signature Winnipeg Airport Hotel & Suites St. James CA $565 per person Jan 12 - Jan 16 found 1 day ago Roundtrip flight included Edmonton (YEG) to Winnipeg (YWG) 9/10 Wonderful! (195 reviews) Great hotel, but had some issues with the lights in the washroom. Reviewed on Nov 24, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-12/2026-01-16/?FromAirport=YEG&Destination=YWG&NumRoom=1&NumAdult=2&NumChild=0&hotelId=110510684&paandie=true&dealMarker=IUXwvjW6OFRUaGAfr46Tstiix4jXI3O1xn8qCFWyqu49EqxA0nm82so6Wce6MFdE) ![Sandman Hotel & Suites Winnipeg Airport](https://images.trvl-media.com/lodging/2000000/1840000/1835800/1835720/7c49870a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sandman Hotel & Suites Winnipeg Airport St. James CA $460 per person Jan 12 - Jan 16 found 1 day ago Roundtrip flight included Edmonton (YEG) to Winnipeg (YWG) 8.2/10 Very Good! (1,408 reviews) Room was OK, the sink stunk though-- like the pipes were rotting probably something that needs fixing, water was also yellowish coming out. Pool area was filthy when we went there about 9:30-- I'm guessing from previous night, there were cups and soaking wet towels all over that we wound up cleaning up ourselves, yuck. The pool opens early so I'm surprised no staff had it cleaned up earlier. Reviewed on Nov 23, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-12/2026-01-16/?FromAirport=YEG&Destination=YWG&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1835720&paandie=true&dealMarker=IUXwvjW6OFRUaGAfr46Tst3kzBGtP22mZyt0zH4GSd-fQeF300cgjAIdM03_DO_h) ![The Fairmont Winnipeg Gold Experience](https://images.trvl-media.com/lodging/65000000/64580000/64577200/64577145/77070d90_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Fairmont Winnipeg Gold Experience Exchange District CA $848 per person Jan 12 - Jan 16 found 1 day ago Roundtrip flight included Edmonton (YEG) to Winnipeg (YWG) 8.6/10 Excellent! (30 reviews) Enjoyed the Fairmont Gold Experience. Gold Lounge was closed for renovations on our last day, but the hotel took great care of us in the restaurant for breakfast. We will be back. Reviewed on Feb 5, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-12/2026-01-16/?FromAirport=YEG&Destination=YWG&NumRoom=1&NumAdult=2&NumChild=0&hotelId=64577145&paandie=true&dealMarker=2WmGQimqJPFS2gxWUypPWeqaPsxWjyGybBw5ZAAZnTiQVMF6liYN9wwa_UBmxMOh) ![Humphry Inn & Suites](https://images.trvl-media.com/lodging/1000000/860000/857300/857263/b2dc02ef_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Humphry Inn & Suites Downtown Winnipeg CA $465 per person Jan 12 - Jan 16 found 1 day ago Roundtrip flight included Edmonton (YEG) to Winnipeg (YWG) 8.2/10 Very Good! (1,479 reviews) After staying here a few times it is reliable when it comes to being reasonably clean and safe. Parking usually available for a cost and walking distance from plenty of places. Reviewed on Nov 29, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-12/2026-01-16/?FromAirport=YEG&Destination=YWG&NumRoom=1&NumAdult=2&NumChild=0&hotelId=857263&paandie=true&dealMarker=2WmGQimqJPFS2gxWUypPWQWNjwkhOrhNus_X5v6jcqf087DoE1D9Pa6Wf3gPmX0F) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=PKG_BF_PROMO_6145346) ## Ready to book your vacation to Headingley? Choose your dates ## Headingley Hotel Deals ![Motel 6 Headingley, MB - Winnipeg West](https://images.trvl-media.com/lodging/5000000/4470000/4464100/4464039/56e2f620_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Motel 6 Headingley, MB - Winnipeg West 4400 Portage Avenue Headingley MB Fully refundable CA $102 CA $114 total Dec 14 - Dec 15 includes taxes & fees 9/10 Wonderful! (1,229 reviews) Clean room , good place to stay Reviewed on Nov 23, 2025 [](https://expedia.ca/Hotel-Search?startDate=14%2F12%2F2025&endDate=15%2F12%2F2025&selected=4464039&PinnedHotelID=4464039&HadPinnedHotel=true®ionId=6145346) ![Best Western Plus Winnipeg West](https://images.trvl-media.com/lodging/8000000/7460000/7450600/7450581/f06a9fda_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Western Plus Winnipeg West 4140 Portage Avenue Headingley MB Fully refundableReserve now, pay when you stay CA $173 CA $194 total Dec 14 - Dec 15 includes taxes & fees 8.8/10 Excellent! (1,009 reviews) Room was good! Staff allowed us to use their breakfast room for our daughter's birthday pizza party free of charge. Pool area was great for children aged 2-6 years old Reviewed on Nov 23, 2025 [](https://expedia.ca/Hotel-Search?startDate=14%2F12%2F2025&endDate=15%2F12%2F2025&selected=7450581&PinnedHotelID=7450581&HadPinnedHotel=true®ionId=6145346) ![Victoria Inn Hotel and Convention Centre Winnipeg](https://images.trvl-media.com/lodging/1000000/20000/13300/13226/94dbadb8_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Victoria Inn Hotel and Convention Centre Winnipeg 1808 Wellington Ave Winnipeg MB Fully refundableReserve now, pay when you stay CA $130 CA $153 total Dec 22 - Dec 23 includes taxes & fees 8.4/10 Very Good! (2,512 reviews) The rooms are so comfortable. The beds are the best I've found, in all of my recent hotel stays. Love the text message that you get as soon as you get to your room. Our guest service representative, Victoriia, was friendly and upbeat. She made sure that all of our questions were answered. The water ... Reviewed on Nov 27, 2025 [](https://expedia.ca/Hotel-Search?startDate=22%2F12%2F2025&endDate=23%2F12%2F2025&selected=13226&PinnedHotelID=13226&HadPinnedHotel=true®ionId=6145346) [See all 520 properties in Headingley](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=30%2F11%2F2025&endDate=01%2F12%2F2025®ionId=6145346) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### 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. [](https://expedia.ca/John-Blumberg-Softball-Complex-Headingley.d6255853.Vacation-Attraction) #### 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. [](https://expedia.ca/Thunder-Rapids-Fun-Park-Headingley.d553248621561234992.Vacation-Attraction) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other ### Lodging - [3 Star Hotels in Birchwood](https://www.expedia.ca/3Star-Birchwood-Winnipeg-Hotels.s30-n873287256046260224-0.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Glendale](https://www.expedia.ca/3Star-Glendale-Winnipeg-Hotels.s30-n873292641928957952-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Birchwood](https://www.expedia.ca/4Star-Birchwood-Winnipeg-Hotels.s40-n873287256046260224-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Buchanan](https://www.expedia.ca/4Star-Buchanan-Winnipeg-Hotels.s40-n873292832054661120-0.Travel-Guide-Filter-Hotels) - [Hotels near Academy Lanes West](https://www.expedia.ca/Academy-Lanes-West-Hotels.0-l642299788980453376-0.Travel-Guide-Filter-Hotels) - [Hotels near Assiniboia Downs](https://www.expedia.ca/Assiniboia-Downs-Hotels.0-l6229713-0.Travel-Guide-Filter-Hotels) - 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[Flights from Victoria (YYJ) to Winnipeg (YWG)](https://www.expedia.ca/lp/flights/yyj/ywg/victoria-to-winnipeg) - [Flights from Toronto (YYZ) to Winnipeg (YWG)](https://www.expedia.ca/lp/flights/yyz/ywg/toronto-to-winnipeg) ### Packages - [Assiniboia Downs](https://www.expedia.ca/Assiniboia-Downs-Winnipeg.d6229713.Vacation-Attraction) - [Assiniboine Park](https://www.expedia.ca/Assiniboine-Park-Winnipeg.d6072403.Vacation-Attraction) - [Assiniboine Park Zoo](https://www.expedia.ca/Assiniboine-Park-Zoo-Winnipeg.d6229708.Vacation-Attraction) - [Beaudry Provincial Park](https://www.expedia.ca/Beaudry-Provincial-Park-Manitoba.d6255869.Vacation-Attraction) - [Bristol Aerospace Limited](https://www.expedia.ca/Bristol-Aerospace-Limited-St-James.d6255153.Vacation-Attraction) - [Brooklands Vacations](https://www.expedia.ca/Brooklands.d57644.Destination-Travel-Guides) - [Canadian Forces Base Winnipeg](https://www.expedia.ca/Canadian-Forces-Base-Winnipeg-Winnipeg.d6255135.Vacation-Attraction) - [Corydon Avenue](https://www.expedia.ca/Corydon-Avenue-Winnipeg.d6340529.Vacation-Attraction) - [Fortwhyte Alive Center](https://www.expedia.ca/FortWhyte-Alive-Center-Winnipeg.d6229677.Vacation-Attraction) - [Glendale Golf and Country Club](https://www.expedia.ca/Glendale-Golf-And-Country-Club-Glendale.d6194090.Vacation-Attraction) - [Grant Park Shopping Centre](https://www.expedia.ca/Grant-Park-Shopping-Centre-Winnipeg.d6257851.Vacation-Attraction) - [Grant's Old Mill Museum](https://www.expedia.ca/Grants-Old-Mill-Museum-Winnipeg.d553248621561214609.Vacation-Attraction) - [John Blumberg Softball Complex](https://www.expedia.ca/John-Blumberg-Softball-Complex-Headingley.d6255853.Vacation-Attraction) - [Kid City](https://www.expedia.ca/Kid-City-St-James.d553248621561214618.Vacation-Attraction) - [Leo Mol Sculputure Garden](https://www.expedia.ca/Leo-Mol-Sculputure-Garden-Winnipeg.d6254180.Vacation-Attraction) - [Little Mountain Park](https://www.expedia.ca/Little-Mountain-Park-Winnipeg.d553248621561214644.Vacation-Attraction) - [Mcphillips Station Casino](https://www.expedia.ca/McPhillips-Station-Casino-Winnipeg.d6226483.Vacation-Attraction) - [Polo Park](https://www.expedia.ca/Polo-Park-Polo-Park.d6154540.Vacation-Attraction) - [Prairie Dog Central Railway](https://www.expedia.ca/Prairie-Dog-Central-Railway-Winnipeg.d6229668.Vacation-Attraction) - [Red River College](https://www.expedia.ca/Red-River-College-Winnipeg.d6255197.Vacation-Attraction) - [Red River Exhibition Park](https://www.expedia.ca/Red-River-Exhibition-Park-Buchanan.d6229627.Vacation-Attraction) - [Saint Francois Xavier Vacations](https://www.expedia.ca/Saint-Francois-Xavier.d3000467910.Destination-Travel-Guides) - [Speedworld Indoor Kart Track](https://www.expedia.ca/Speedworld-Indoor-Kart-Track-St-James.d553248621561234976.Vacation-Attraction) - [The Players Course](https://www.expedia.ca/The-Players-Course-Winnipeg.d553248621532864612.Vacation-Attraction) - [Thunder Rapids Fun Park](https://www.expedia.ca/Thunder-Rapids-Fun-Park-Headingley.d553248621561234992.Vacation-Attraction) - [Tuxedo Vacations](https://www.expedia.ca/Tuxedo.d57493.Destination-Travel-Guides) - [U-Puttz Thrill Zone](https://www.expedia.ca/U-Puttz-Thrill-Zone-Winnipeg.d553248621532864894.Vacation-Attraction) - [Unicity Mall](https://www.expedia.ca/Unicity-Mall-Winnipeg.d553248621585428171.Vacation-Attraction) - [University of Winnipeg](https://www.expedia.ca/University-Of-Winnipeg-Winnipeg.d6072399.Vacation-Attraction) - [Visit Birchwood](https://www.expedia.ca/Winnipeg-Birchwood.dx873287256046260224) - [Visit Westdale](https://www.expedia.ca/Winnipeg-Westdale.dx873292502896168960) - [Winnipeg Vacations](https://www.expedia.ca/Winnipeg.d6141041.Destination-Travel-Guides) ### Cars - [Car rentals near Academy Lanes West](https://www.expedia.ca/Car-Rentals-In-Academy-Lanes-West.d642299788980453376.Car-Rental-Guide) - [Rental cars Winnipeg James Armstrong Richardson Intl. airport](https://www.expedia.ca/Car-Rentals-In-Winnipeg-James-Armstrong-Richardson-Intl.d4675417.Car-Rental-Guide) - [Car rentals near Winnipeg](https://www.expedia.ca/Car-Rentals-In-Winnipeg.d6141041.Car-Rental-Guide) ### Other - [Things to do in Winnipeg](https://www.expedia.ca/Things-To-Do-In-Winnipeg.d6141041.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.