Headingley Vacations

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Find the Best Headingley Vacation Packages

Headingley Hotel Deals

Best Western Plus Winnipeg West

Best Western Plus Winnipeg West

2.5 out of 5
4140 Portage Avenue Headingley MB
Fully refundableReserve now, pay when you stay
The price is SARĀ 491 per night from Jul 26 to Jul 27
SARĀ 491
SARĀ 550 total
26 Jul - 27 Jul
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
"Pool was EXCELLENT and room clean , breakfast could benefit from better fresh fruit (red delicious and out of season oranges were provided- what about some blueberries and strawberries?) and more healthful options. I've been to other Best Westerns with fantastic breakfasts so this was disappointing. ..."

Reviewed on 20 July 2026

Best Western Plus Winnipeg West
Motel 6 Headingley, MB - Winnipeg West

Motel 6 Headingley, MB - Winnipeg West

2 out of 5
4400 Portage Avenue Headingley MB
Fully refundableReserve now, pay when you stay
The price is SARĀ 467 per night from Jul 27 to Jul 28
SARĀ 467
SARĀ 523 total
27 Jul - 28 Jul
includes taxes & fees
9.2/10 Wonderful! (1,581 reviews)
"I enjoyed our stay very much. The only complaint I had was the lack of breakfast. Other then that, it was perfect šŸ‘Œ"

Reviewed on 19 July 2026

Motel 6 Headingley, MB - Winnipeg West
Victoria Inn Hotel and Convention Centre Winnipeg

Victoria Inn Hotel and Convention Centre Winnipeg

3 out of 5
1808 Wellington Ave Winnipeg MB
Fully refundableReserve now, pay when you stay
The price is SARĀ 435 per night from Aug 6 to Aug 7
SARĀ 435
SARĀ 514 total
6 Aug - 7 Aug
includes taxes & fees
8.4/10 Very Good! (3,167 reviews)
"Was a decent stay - only thing that weirded us out was the multiple security guards outside our door on the second floor."

Reviewed on 20 July 2026

Victoria Inn Hotel and Convention Centre Winnipeg
See all 669 properties in Headingley
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 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.
See properties

Frequently asked questions

How much does a Headingley vacation package cost?
You can snap up a vacation package to this top destination 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 traveling in January, October and November. You'll typically find lower prices on flights and hotels during these quieter months ā€” perfect for budget-conscious travelers.
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?

  1. Choose your dates: What you want to do in Headingley and your preferred season can help you decide when to go.
  2. 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.
  3. 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.
  4. Combine your airfare and accommodations: After you've nailed down your travel dates and duration, lock in the perfect Headingley vacation package for you.