Title: Headingley Vacation Packages 2026 from $1,020 | Expedia.com [Headingley Travel Guide](https://expedia.com/Headingley.dx6145346)[Hotels in Headingley](https://expedia.com/Headingley-Hotels.d6145346.Travel-Guide-Hotels)[Vacation Rentals in Headingley](https://expedia.com/Headingley-Vacation-Rentals.d6145346.Travel-Guide-VacationRentals)[Flights to Headingley](https://expedia.com/Cheap-Flights-To-Headingley.d6145346.Travel-Guide-Flights)[Car Rentals in Headingley](https://expedia.com/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 Vacations from $1,020 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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.com/Assiniboia-Downs-Winnipeg.d6229713.Vacation-Attraction), [BellMTS Iceplex](https://www.expedia.com/BellMTS-Iceplex-Winnipeg.d553248635026762217.Vacation-Attraction) and [Unicity Mall](https://www.expedia.com/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. ## The Latest Headingley vacation packages Price found within the past 48 hours. Click for updated prices. ![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 $1,020 per person Mar 12 - Mar 15 found 1 hour ago Roundtrip non-stop flight included Denver (DEN) to Winnipeg (YWG) 8/10 Very Good! (1,105 reviews) The front staff person upgraded us to one of the newly renovated suites. The room was fantastic. The rest of the staff were excellent and went out of there way to help us whenever we needed it. Reviewed on Feb 4, 2026 ![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 $1,032 per person Mar 12 - Mar 15 found 1 hour ago Roundtrip non-stop flight included Denver (DEN) to Winnipeg (YWG) 8.2/10 Very Good! (1,479 reviews) Was pleasantly surprised. Very clean and comfortable. Reasonably priced. Reviewed on Feb 9, 2026 ![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 $1,028 per person Mar 12 - Mar 15 found 1 hour ago Roundtrip non-stop flight included Denver (DEN) to Winnipeg (YWG) 8.4/10 Very Good! (2,464 reviews) Kids were running up the hallways till all hrs of the night! Reviewed on Feb 6, 2026 ![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 $1,025 per person Mar 12 - Mar 15 found 1 hour ago Roundtrip non-stop flight included Denver (DEN) to Winnipeg (YWG) 8.4/10 Very Good! (1,001 reviews) The room was very clean and the housekeeping staff was efficient and friendly. Reviewed on Feb 8, 2026 ![Canad Inns Destination Centre Club Regent Casino Hotel](https://images.trvl-media.com/lodging/1000000/590000/583700/583630/c7554b08_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Canad Inns Destination Centre Club Regent Casino Hotel Transcona $1,023 per person Mar 12 - Mar 15 found 1 hour ago Roundtrip non-stop flight included Denver (DEN) to Winnipeg (YWG) 9/10 Wonderful! (1,380 reviews) Everything was great Reviewed on Feb 8, 2026 Don't see what you're looking for? See all available trips from Columbus to Headingley [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-10/2026-03-17/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=YWG&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### 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.com/John-Blumberg-Softball-Complex-Headingley.d6255853.Vacation-Attraction) ## 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 $88 nightly $98 total Mar 2 - Mar 3 Total with taxes and fees 9/10 Wonderful! (1,363 reviews) very clean Reviewed on Feb 9, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F2%2F2026&endDate=3%2F3%2F2026&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 $128 nightly $143 total Mar 2 - Mar 3 Total with taxes and fees 8.8/10 Excellent! (1,005 reviews) Nice Reviewed on Feb 3, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F2%2F2026&endDate=3%2F3%2F2026&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 8.4/10 Very Good! (2,798 reviews) All was well Reviewed on Feb 6, 2026 [Get rates](https://expedia.com/Hotel-Search?startDate=2%2F24%2F2026&endDate=2%2F25%2F2026&selected=13226&PinnedHotelID=13226&HadPinnedHotel=true®ionId=6145346) [](https://expedia.com/Hotel-Search?startDate=2%2F24%2F2026&endDate=2%2F25%2F2026&selected=13226&PinnedHotelID=13226&HadPinnedHotel=true®ionId=6145346) [See all 566 properties in Headingley](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F11%2F2026&endDate=2%2F12%2F2026®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. ## Find the Best Headingley Vacation Packages ## Headingley Essential Information | Language | English | | --------------- | ---------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | Canadian dollars | | Closest Airport | Winnipeg James Armstrong Richardson Intl. Airport (YWG) | | Population | 3,200 | | Max Temp Winter | 12ºF | | Max Temp Summer | 75ºF | | Top Sights | [Assiniboine Park Zoo](https://www.expedia.com/Assiniboine-Park-Zoo-Winnipeg.d6229708.Vacation-Attraction), [Celebrations Dinner Theatre](https://www.expedia.com/Celebrations-Dinner-Theatre-Fort-Garry.d553248621532864891.Vacation-Attraction) and [Burton Cummings Theatre](https://www.expedia.com/Burton-Cummings-Theatre-Winnipeg.d6229642.Vacation-Attraction) | ## More vacations you might like ![](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.com/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 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Headingley? ### How many days is enough for Headingley? ### Is it worth booking a vacation package to Headingley? ### How to find the best Headingley package deals? ### Is it cheaper to book a Headingley vacation as a package? ### When to book a vacation package to Headingley? ### Does Expedia offer Book Now, Pay Later Headingley vacation packages? \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save even more - get up to 20% on select hotels when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app