Headingley Vacations

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Find the Best Headingley Vacation Packages

Headingley Hotel Deals

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 AED 322 per night from Mar 1 to Mar 2
AED 322
AED 361 total
1 Mar - 2 Mar
includes taxes & fees
9/10 Wonderful! (1,353 reviews)
Clean, affordable, great staff

Reviewed on 4 February 2026

Motel 6 Headingley, MB - Winnipeg West
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 AED 469 per night from Feb 22 to Feb 23
AED 469
AED 525 total
22 Feb - 23 Feb
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
Nice

Reviewed on 3 February 2026

Best Western Plus 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
8.4/10 Very Good! (2,798 reviews)
All was well

Reviewed on 6 February 2026

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Victoria Inn Hotel and Convention Centre Winnipeg
See all 566 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.

Discover the most popular places to visit in Headingley

John Blumberg Golf Course

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 Golf Course

Thunder Rapids Fun Park

Bring the kiddos to Thunder Rapids Fun Park and enjoy some excitement at this theme park in Headingley. Stroll along the riverfront or attend a sporting event in the area.

Thunder Rapids Fun Park

Frequently asked questions

How do I find cheap flights to Headingley that have flexible change policies?
It's as easy as can be with Expedia. Step 1: Type in your travel dates and destination and click on "Search." Step 2? Check "No change fee" directly underneath the "Flexible change policies" filter to the left of your screen. Step 3. Snag a flexible and cheap flight to Headingley.
Which airlines fly to Headingley?
Dig out your passport, pack your bags and take your pick of these leading airlines that service Headingley:

  • Delta Air Lines - 86 flights to or near Headingley each month, including 86 flights to Winnipeg James Armstrong Richardson Intl. Airport (YWG) per month.
  • WestJet - 30 flights to or near Headingley each month, including 30 flights to Winnipeg James Armstrong Richardson Intl. Airport (YWG) per month.
  • Flair Airlines - 8 flights to or near Headingley each month, including 8 flights to Winnipeg James Armstrong Richardson Intl. Airport (YWG) per month.

How can I find cheap tickets to Headingley?
Book ahead of time, consider nearby airports, avoid vacation periods — there are lots of ways! Another one is to make the most of Expedia's "flexible dates" function. Search for your Headingley flight, then check out the prices for nearby dates. In the last seven days, the lowest price for a flight to Headingley was .
How much is a flight to Headingley?
You could have purchased a round-trip ticket to Headingley from anywhere between and in the last seven days. For one-way journeys taking off from (), the lowest price during this period was .
What are the most popular airports to fly into in Headingley?
Get ready to pack your suitcase and fly into Winnipeg James Armstrong Richardson Intl. Airport (YWG), Headingley's main flight hub. Book one of the 125 flights that land at this favorite destination every month.
When is the cheapest time to fly to Headingley?
If you can be flexible with what date you jet off to Headingley, try to depart early on in the week. The cheapest day to take off is usually Tuesday, followed by Monday. Saturday is typically the costliest day, with lots of vacationers preferring to take off on the weekend.
How much is a plane ticket to Headingley?
Prices ranged anywhere from to over the last seven days. When you're ready to book, we're here to help grab an amazing deal to Headingley.
What months are the cheapest to book a flight to Headingley?
February is the cheapest month to lock in a seat for your Headingley escape. Tickets are priciest throughout the busy month of December, so steer clear of this time if possible.