A rural landscape with a field of tall grass, two grain silos, and a wooden barn under a colorful sky.

Headingley Vacations from $768

Book a Hotel + Flight or Car together to unlock savings

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.

The Latest Headingley Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Jan 12 - Jan 16

    Canad Inns Destination Centre Garden City + Flight

    Leila-McPhillips Triangle
    4 nights
    3.0 star property
    8.2/10 - Very good (1,021 reviews)
    Roundtrip • Punta Cana (PUJ) - Winnipeg (YWG)
    PUJ - YWG • 1 stop YWG - PUJ • 1 stop
    $858
    $768
    per traveler
    found 1 day ago
    Canad Inns Destination Centre Garden City
  • Jan 12 - Jan 16

    Humphry Inn & Suites + Flight

    Downtown Winnipeg
    4 nights
    2.5 star property
    8.4/10 - Very good (1,779 reviews)
    Roundtrip • Punta Cana (PUJ) - Winnipeg (YWG)
    PUJ - YWG • 1 stop YWG - PUJ • 1 stop
    $988
    $856
    per traveler
    found 1 day ago
    Humphry Inn & Suites
  • Jan 12 - Jan 16

    Country Inn & Suites by Radisson, Winnipeg, MB + Flight

    St. James
    4 nights
    2.5 star property
    7.6/10 - Good (1,001 reviews)
    Roundtrip • Punta Cana (PUJ) - Winnipeg (YWG)
    PUJ - YWG • 1 stop YWG - PUJ • 1 stop
    $986
    $858
    per traveler
    found 1 day ago
    Country Inn & Suites by Radisson, Winnipeg, MB
  • Jan 12 - Jan 16

    Canad Inns Destination Centre Transcona + Flight

    Transcona
    4 nights
    3.0 star property
    8.4/10 - Very good (1,004 reviews)
    "Hotel was great, nice very clean, awesome location!"
    Reviewed November 11, 2026
    Roundtrip • Punta Cana (PUJ) - Winnipeg (YWG)
    PUJ - YWG • 1 stop YWG - PUJ • 1 stop
    $919
    $803
    per traveler
    found 1 day ago
    Canad Inns Destination Centre Transcona
  • Jan 12 - Jan 16

    Victoria Inn Hotel and Convention Centre Winnipeg + Flight

    St. James
    4 nights
    3.0 star property
    8.4/10 - Very good (3,342 reviews)
    Roundtrip • Punta Cana (PUJ) - Winnipeg (YWG)
    PUJ - YWG • 1 stop YWG - PUJ • 1 stop
    $944
    $830
    per traveler
    found 1 day ago
    Victoria Inn Hotel and Convention Centre Winnipeg

Where to stay near Headingley

Discover the charm of Headingley, a hub of excitement perfect for family and city vacations. Enjoy friendly atmospheres, explore nearby neighborhoods, and indulge in entertainment options that cater to both business and leisure travelers. Your adventure awaits in this welcoming Canadian destination!

Westdale

For travelers seeking a vibrant city experience, Westdale offers a perfect base to explore Winnipeg's attractions. Just about 3 miles away from Headingley, this neighborhood provides easy access to diverse activities, including the Red River Exhibition Park and the Glendale Golf and Country Club. With its blend of shopping options and cultural sites like the University of Winnipeg and local sports facilities, Westdale caters to families, budget-conscious visitors, and business travelers alike. Choosing Westdale for your stay ensures a delightful combination of convenience and excitement.

Glendale

Plan your stay in Glendale, a top-rated choice for travelers eager to explore the vibrant attractions of Winnipeg. This neighborhood offers easy access to popular spots like the Red River Exhibition Park, Glendale Golf and Country Club, and the Historical Museum of St. James - Assiniboia, making it ideal for those interested in sports, family activities, and cultural experiences. Located about 3 miles away from Headingley, Glendale provides a smart booking choice with its blend of leisure and adventure opportunities.

Oak Bluff

If you are a nature-loving traveler, look no further than Oak Bluff, which features stunning outdoor experiences like the nearby national state park and the FortWhyte Alive Center. Families and business travelers alike will appreciate the recreational area and golf courses that make this city an ideal retreat. Situated about 7 miles from Headingley, Oak Bluff is a smart choice for your stay, offering a perfect blend of relaxation and adventure.

Saint Francois Xavier

Saint Francois Xavier stands out as a prime spot for travelers interested in cultural experiences, family-friendly activities, and outdoor adventures. With attractions like Beaudry Provincial Park, Red River Exhibition Park, and Glendale Golf and Country Club, visitors can enjoy scenic landscapes and recreational opportunities year-round. Located about 7 miles from Headingley, this charming city offers easy access to shopping and nature, making it a smart choice for your vacation stay.

King Edward

Travelers visiting the area often choose King Edward, especially those seeking a blend of business, family, and cultural experiences. This vibrant neighborhood offers easy access to wellness and relaxation venues, with highlights like the RBC Convention Centre and the University of Winnipeg nearby. For shopping and local flavor, Corydon Avenue is just a short drive away. Located about 8 miles by car from Headingley, King Edward is a smart choice for those looking to explore Winnipeg's diverse offerings.

Discover the most popular places to visit in Headingley

Headingley Hotel Deals

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.

Frequently Asked Questions

How much does a Headingley vacation package cost?

You can pick up a vacation package to this top destination from $768 on Expedia. However, how much your vacation 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?

You can typically find lower prices and greater availability in November, December and January. Take a look at our cheap Headingley vacation packages and you could land some great off-season discounts.

How many days is enough for Headingley?

Headingley vacations come in all shapes and sizes, but to get a true feel for this destination, we'd say 2 days is about right. This will mean you can fit in top sights like John Blumberg Softball Complex and John Blumberg Golf Course and track down some hidden gems. Don't forget to visit neighborhoods such as Westdale and Buchanan either. If you're clever with your time, you can even allow for a day trip or two from Headingley too.

Is it worth booking a vacation package to Headingley?

Headingley is a good vacation destination with attractions like BellMTS Iceplex among the many things to keep you busy. Whether you're heading away with the family or planning a trip with friends, a Headingley vacation promises a good time 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 traveling on a weekday, when prices are usually lower.

Is it cheaper to book a Headingley vacation as a package?

An Expedia vacation package could land you significant savings when compared to booking accommodations and flights individually. Better still, you can personalize 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 vacation 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.

Does Expedia offer Book Now, Pay Later Headingley vacation packages?

If you're anything like us, you love exploring new places but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the overall cost of your Headingley break across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you see them.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.