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.
Morden Motor Inn
CA $352
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Winnipeg (YWG)
7.2/10 Good! (57 reviews)
Clean room but wasn't fiven any fresh towels garbage bags or fresh water coffee suger or cream beds were surprisingly good like new tv was alright but was all fuzzy whe first got into the room
Reviewed on Aug 8, 2026
Days Inn & Suites by Wyndham Brandon
CA $460
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Winnipeg (YWG)
8.8/10 Excellent! (1,004 reviews)
The hotel is very clean and the staff were really friendly and helpful. They were very accommodating when we requested a later checkout. I had the best sleeps, the beds are so comfortable! The pool was really disappointing, as it’s very shallow (it would be great for families with small children). We were excited to have a room with a balcony but we didn’t really get to enjoy as it was close to the entrance and there was so much cigarette smoke that came up to us. There was even an ashtray on our balcony table. My son has asthma, so it was more than just being bothered by the smell. The hotel is next door to T-Birds Bowling which was great for hours of fun and yummy pizza.
Reviewed on Aug 13, 2026
Ready to book your vacation to Headingley?
Headingley Hotel Deals
Best Western Plus Winnipeg West
4140 Portage Avenue Headingley MB
Fully refundableReserve now, pay when you stay
CA $192
CA $215 total
Aug 16 - Aug 17
includes taxes & fees
9/10 Wonderful! (1,015 reviews)
"The breakfast , clean rooms,"
Reviewed on Aug 12, 2026
Motel 6 Headingley, MB - Winnipeg West
4400 Portage Avenue Headingley MB
Fully refundableReserve now, pay when you stay
CA $150
CA $168 total
Aug 30 - Aug 31
includes taxes & fees
Victoria Inn Hotel and Convention Centre Winnipeg
1808 Wellington Ave Winnipeg MB
Fully refundableReserve now, pay when you stay
CA $169
CA $200 total
Sep 3 - Sep 4
includes taxes & fees
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 $352 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.
