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
CA $451
per person
Nov 12 - Nov 15
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to Winnipeg (YWG)
8/10 Very good! (1,432 reviews)
Clean room, nice staff, nice breakfast deal! Even had a place for me to invest $20…lol(slots)
Reviewed on Sep 18, 2026
Canad Inns Destination Centre Club Regent Casino Hotel
Transcona
CA $509
per person
Nov 12 - Nov 15
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to Winnipeg (YWG)
9/10 Wonderful! (1,782 reviews)
It was our 1st Anniversary and I tried to surprise my wife and have our daughter decorate the room while we were at dinner and the staff was rude to her and tried to stop her. Then when my daughter called to tell me my wife found out....SURPRISE RUINED! AND there are no managers on the weekends apparently I was told. If you prefer great customer service PLEASE STAY AWAY!
Reviewed on Sep 19, 2026
Ready to book your vacation to Headingley?
Headingley Hotel Deals
Motel 6 Headingley, MB - Winnipeg West
4400 Portage Avenue Headingley MB
Fully refundableReserve now, pay when you stay
CA $145
CA $162 total
Oct 5 - Oct 6
includes taxes & fees
9.2/10 Wonderful! (1,643 reviews)
"Great place to stay if you have Dogs!! They are very friendly and All rooms are dog friendly!! This is our second stay there and will be staying more and more!!!"
Reviewed on Sep 19, 2026
Best Western Plus Winnipeg West
4140 Portage Avenue Headingley MB
Fully refundableReserve now, pay when you stay
CA $187
CA $209 total
Sep 27 - Sep 28
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"The rooms were spacious and very clean, and the bed and pillows were incredibly comfortable. It was also nice and quiet, which made for a really relaxing stay. The front desk and housekeeping staff were all friendly, welcoming, and helpful. The pool and waterslide were so much fun, and I really enjoyed ..."
Reviewed on Sep 19, 2026
Victoria Inn Hotel and Convention Centre Winnipeg
1808 Wellington Ave Winnipeg MB
Fully refundableReserve now, pay when you stay
CA $174
CA $206 total
Oct 11 - Oct 12
includes taxes & fees
8.4/10 Very good! (3,222 reviews)
"Clean room, staff was helpful"
Reviewed on Sep 19, 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.
Stay near popular Headingley attractions
John Blumberg Golf Course
8.4/10 (12 reviews)
Enjoy a round of golf in Headingley at John Blumberg Golf Course. Experience the area's fascinating museums or attend a sporting event.
John Blumberg Softball Complex
8.0/10 (13 reviews)
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.
Frequently asked questions
How much does a Headingley vacation package cost?
You can snap up a vacation package to this top destination from CA $386 on Expedia. But how much your vacation to Headingley costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Headingley?
If you're looking to snag a cheap Headingley vacation package, consider travelling in January, October and November. You'll typically find lower prices on flights and hotels during these quieter months — perfect for budget-conscious travellers.
How many days is enough for Headingley?
To get the most out of a Headingley vacation, we recommend staying for 2 days. Divide your time between visiting BellMTS Iceplex, Academy Lanes West and other major sights, in addition to experiencing neighbourhoods like Westdale and Buchanan. If you've got some spare time, add a day trip to your Headingley vacation itinerary.
Is it worth booking a vacation package to Headingley?
Headingley offers everything you need for an amazing escape. Get your Headingley vacation off to a flying start by visiting major attractions like BellMTS Iceplex.
How to find the best Headingley package deals?
Use Expedia's filter tool to find some terrific Headingley package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or look for Headingley package deals in the low season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Headingley vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and stays individually. Better still, you can customize your Headingley escape to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Headingley?
If you have your Headingley travel dates finalized, book early to grab some awesome deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are ideal for setting off on a whim.
How to plan a trip to Headingley?
- Choose your dates: What you want to do in Headingley and your preferred season can help you decide when to go.
- Figure out your budget: Ensure you have enough money to cover everything from transportation and dining out to experiences and flights. Your hotel will probably be the largest expense during your trip to Headingley.
- Decide your trip length: Think about how much time you want to spend discovering Headingley. Plan your days so you can get to all the attractions and activities you're interested in without rushing.
- Combine your airfare and accommodations: After you've nailed down your travel dates and duration, lock in the perfect Headingley vacation package for you.
Explore a world of travel with Expedia
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
