Headingley Holidays
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- Better togetherSave up to S$1,300 when you book a flight and hotel together*
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Top hotels in Headingley
Best Western Plus Winnipeg West
4140 Portage Avenue Headingley MB
Fully refundableReserve now, pay when you stay
S$197
11 Aug - 12 Aug
includes taxes & fees
9/10 Wonderful! (1,010 reviews)
"Beau buffet déjeuner , lit confortable"
Reviewed on 6 Aug, 2026
Motel 6 Headingley, MB - Winnipeg West
4400 Portage Avenue Headingley MB
Fully refundableReserve now, pay when you stay
S$164
16 Aug - 17 Aug
includes taxes & fees
9.2/10 Wonderful! (1,605 reviews)
"Was an awesome stay. Welcoming, clean and friendly staff."
Reviewed on 7 Aug, 2026
Victoria Inn Hotel and Convention Centre Winnipeg
1808 Wellington Ave Winnipeg MB
Fully refundableReserve now, pay when you stay
S$186
31 Aug - 1 Sept
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)
This 27-hole golf haven features rolling fairways and strategic water hazards along the Assiniboine River. Enjoy both the challenging Emerald Course and more accessible Gold Course.
John Blumberg Softball Complex
8.0/10 (13 reviews)
This premier softball venue has hosted the Pan American Games with its seven immaculate diamonds. Catch the excitement of national tournaments while enjoying refreshments from the sports bar and concession stand.
Frequently asked questions
How much does a Headingley holiday package cost?
You can pick up a holiday package to this top destination on Expedia. However, how much your holiday to Headingley costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Headingley?
If you're hoping to book a cheap Headingley holiday package, consider planning a trip in January, October and November. You'll typically find better rates on airfares and hotels during these quieter months — ideal for budget-conscious travellers.
How many days is enough for Headingley?
We recommend booking a Headingley holiday for a minimum of 2 days. This will allow you enough time to visit top attractions including John Blumberg Softball Complex and John Blumberg Golf Course, as well as check out neighbourhoods like Westdale and Buchanan. You might even be able to fit in a day trip beyond Headingley.
Is it worth booking a holiday package to Headingley?
Headingley is a good holiday destination with attractions like BellMTS Iceplex among the many things to keep you entertained. Whether you're heading away with the family or getting away with friends, a Headingley holiday promises fun for everyone.
How to find the best Headingley package deals?
Landing a cheap Headingley package deal is easy with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget, apply some filters and see what's available. You can tweak your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Headingley package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Headingley holiday as a package?
An Expedia holiday package could land you significant savings when compared to booking accommodation and flights individually. Better still, you can personalise your Headingley escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a holiday package to Headingley?
Score amazing discounts by reserving your flights in advance with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Headingley escape.
How to plan a trip to Headingley?
- Choose when to get away: Check your calendar and get packing. Your favourite season and the activities available will also help you decide when to holiday in Headingley.
- Figure out your budget: Ensure you have enough money to cover everything from transportation and food to activities and airfares. Your hotel will likely be the biggest expense during your trip to Headingley.
- Work out your trip length: Think about how long you want to spend exploring Headingley. Plan your days so you can get to all the activities and attractions you're interested in at a comfortable pace.
- Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a personalised Headingley holiday package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
