Title: Headingley Vacation Packages & Trips 2025/2026 from CA $340 | 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 - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place #### 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. ![Canad Inns Destination Centre Transcona](https://images.trvl-media.com/lodging/6000000/5430000/5424800/5424791/ade61ad2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Canad Inns Destination Centre Transcona Transcona CA $340 per person Feb 3 - Feb 6 found 16 hours ago Roundtrip flight included Vancouver (YVR) to Winnipeg (YWG) 16.8/10 Exceptional! (1,001 reviews) Our room was great, clean, beds were comfortable. Pillows were comfortable. Hot tub was nice and hot. Bathroom was very small but nice. Will stay again. Reviewed on Nov 15, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-03/2026-02-06/?FromAirport=YVR&Destination=YWG&NumRoom=1&NumAdult=2&NumChild=0&hotelId=5424791&paandie=true&dealMarker=_Tm_7KZNWR3Ev-ebJ8VodOUpePl4WL2U2Aq828GD_EhgQIFsawu5NjSQadCXbNyh) ![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 $388 per person Feb 3 - Feb 6 found 16 hours ago Roundtrip flight included Vancouver (YVR) to Winnipeg (YWG) 16.4/10 Exceptional! (1,479 reviews) All staff were amazing Reviewed on Nov 18, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-03/2026-02-06/?FromAirport=YVR&Destination=YWG&NumRoom=1&NumAdult=2&NumChild=0&hotelId=857263&paandie=true&dealMarker=_Tm_7KZNWR3Ev-ebJ8VodNA4RiFEiN-rbYywlNEd2baaECB3vse2oE38ywDVrZLG) ![Canad Inns Destination Centre Fort Garry](https://images.trvl-media.com/lodging/1000000/60000/53000/52976/66851e8c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Canad Inns Destination Centre Fort Garry Fort Garry CA $351 per person Feb 3 - Feb 6 found 16 hours ago Roundtrip flight included Vancouver (YVR) to Winnipeg (YWG) 16/10 Exceptional! (1,105 reviews) Clean room, great amenities Reviewed on Nov 18, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-03/2026-02-06/?FromAirport=YVR&Destination=YWG&NumRoom=1&NumAdult=2&NumChild=0&hotelId=52976&paandie=true&dealMarker=_Tm_7KZNWR3Ev-ebJ8VodNA4RiFEiN-rbYywlNEd2bYeMrNigjSOGeYIrlU1W4gL) ![Best Western Plus Winnipeg Airport Hotel](https://images.trvl-media.com/lodging/1000000/530000/528400/528324/7b759a8d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Best Western Plus Winnipeg Airport Hotel St. James CA $401 per person Jan 30 - Feb 2 found 15 hours ago Roundtrip flight included Toronto (YYZ) to Winnipeg (YWG) 7.6/10 Good! (1,400 reviews) IT was amazing, I would stay again Reviewed on Nov 16, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-30/2026-02-02/?FromAirport=YYZ&Destination=YWG&NumRoom=1&NumAdult=2&NumChild=0&hotelId=528324&paandie=true&dealMarker=j48UxHZ8T8gfKTRL-rsP035zU3AciGrnOkXayPJxkEYyHjHpIVeEK_K6L3KmuGTn) ![Hilton Winnipeg Airport Suites](https://images.trvl-media.com/lodging/1000000/10000/3200/3170/41549918_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Winnipeg Airport Suites St. James CA $470 per person Jan 30 - Feb 2 found 15 hours ago Roundtrip flight included Toronto (YYZ) to Winnipeg (YWG) 17.2/10 Exceptional! (1,005 reviews) Close to the Airport with Shuttle service. Nice spacious suite. Front desk and Maid service was fantastic. Reviewed on Nov 18, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-30/2026-02-02/?FromAirport=YYZ&Destination=YWG&NumRoom=1&NumAdult=2&NumChild=0&hotelId=3170&paandie=true&dealMarker=j48UxHZ8T8gfKTRL-rsP035zU3AciGrnOkXayPJxkEa2iYhb0rxlO4_1zE_RrIYE) ## 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 refundableReserve now, pay when you stay CA $102 CA $114 total Nov 26 - Nov 27 includes taxes & fees 9/10 Wonderful! (1,211 reviews) The staff was very friendly I would have liked a coffee maker in the room Reviewed on Nov 17, 2025 [](https://expedia.ca/Hotel-Search?startDate=26%2F11%2F2025&endDate=27%2F11%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 2 - Dec 3 includes taxes & fees 8.8/10 Excellent! (1,003 reviews) Ran out of food. But good varity Reviewed on Nov 17, 2025 [](https://expedia.ca/Hotel-Search?startDate=02%2F12%2F2025&endDate=03%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 14 - Dec 15 includes taxes & fees 8.4/10 Very Good! (2,463 reviews) Staff was fantastic! Some of the guests not so much unfortunately. Reviewed on Nov 15, 2025 [](https://expedia.ca/Hotel-Search?startDate=14%2F12%2F2025&endDate=15%2F12%2F2025&selected=13226&PinnedHotelID=13226&HadPinnedHotel=true®ionId=6145346) [See all 517 properties in Headingley](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=20%2F11%2F2025&endDate=21%2F11%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. 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Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)