Headingley Holidays from £866

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Your Headingley Holiday

When a getaway to the city is calling, answer it with a holiday package to Headingley. The neighbourhood 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 holiday is a couple of clicks away with Expedia.

Top Headingley Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Humphry Inn & Suites

Humphry Inn & Suites

2.5 out of 5
Downtown Winnipeg
Price was £1,068, price is now £866 per person
£866
per person
10 Sept - 16 Sept
found 1 day ago
Return direct flight included
Glasgow (GLA) to Winnipeg (YWG)
8.4/10 Very good! (1,633 reviews)
All good, no complaints

Reviewed on 9 Jul 2026

Inn At The Forks

Inn At The Forks

3.5 out of 5
Downtown Winnipeg
Price was £1,417, price is now £1,163 per person
£1,163
per person
10 Sept - 16 Sept
found 1 day ago
Return direct flight included
Glasgow (GLA) to Winnipeg (YWG)
9/10 Wonderful! (1,009 reviews)
So convenient and close to a variety of activities!

Reviewed on 8 Jul 2026

Sandman Hotel & Suites Winnipeg Airport

Sandman Hotel & Suites Winnipeg Airport

3 out of 5
St. James
Price was £1,186, price is now £982 per person
£982
per person
10 Sept - 16 Sept
found 1 day ago
Return direct flight included
Glasgow (GLA) to Winnipeg (YWG)
8.2/10 Very good! (1,739 reviews)
It was noisy this time round!

Reviewed on 7 Jul 2026

Sandman Signature Winnipeg Airport Hotel & Suites

Sandman Signature Winnipeg Airport Hotel & Suites

4 out of 5
St. James
Price was £1,229, price is now £1,020 per person
£1,020
per person
10 Sept - 16 Sept
found 1 day ago
Return direct flight included
Glasgow (GLA) to Winnipeg (YWG)
9.2/10 Wonderful! (451 reviews)
Checking in and out was good. The staff were very kind.

Reviewed on 6 Jul 2026

Victoria Inn Hotel and Convention Centre Winnipeg

Victoria Inn Hotel and Convention Centre Winnipeg

3 out of 5
St. James
Price was £1,237, price is now £1,046 per person
£1,046
per person
9 Sept - 15 Sept
found 1 hour ago
Return direct flight included
Glasgow (GLA) to Winnipeg (YWG)
8.4/10 Very good! (3,133 reviews)
Pool was perfect for our youngest, a little too small/shallow for my oldest.

Reviewed on 8 Jul 2026

Headingley Essential Information

Language
English
Currency
Canadian dollars
Closest Airport
Winnipeg James Armstrong Richardson Intl. Airport (YWG)
Population
3,200
Max Temp Winter
-11.11ºC
Max Temp Summer
24ºC
Top Sights
Assiniboine Park Zoo, Celebrations Dinner Theatre and Burton Cummings Theatre

Top hotels in Headingley

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 £100 per night from 9 Aug to 10 Aug
£100
9 Aug - 10 Aug
includes taxes & fees
9.2/10 Wonderful! (1,568 reviews)
"More Kleenex tissue in the rooms!"

Reviewed on 9 Jul 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 £109 per night from 2 Aug to 3 Aug
£109
2 Aug - 3 Aug
includes taxes & fees
9/10 Wonderful! (1,009 reviews)
"Room was clean and they let us check in a little early so we didn’t have to wander the city. Much appreciated!"

Reviewed on 5 Jul 2026

Best Western Plus Winnipeg West
The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel

The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel

4 out of 5
222 Broadway Winnipeg MB
Fully refundable
The price is £124 per night from 31 Jul to 1 Aug
£124
31 Jul - 1 Aug
includes taxes & fees
9.2/10 Wonderful! (1,229 reviews)
"The room was beautiful. And the staff was excellent."

Reviewed on 9 Jul 2026

The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel
See all 662 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

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

Why should I book my Headingley holiday with Expedia?
Expedia has your back for all aspects of your upcoming Headingley holiday. You'll always land the best prices around, but when you bundle your flights, accommodation and/or hire car into a holiday package, you'll score even bigger savings. Want to truly make the most of your adventure? Add a few exciting tours and activities to your package. We offer flexible cancellation policies on almost all bookings, so you won't need to worry if you have to change your plans. Visit our Customer Service Portal link to learn more.
When is the best time of year to holiday in Headingley?
Headingley is busy in July, August and September. If you're not into crowds and prefer a calmer pace, book your trip for November, December and January. With average daytime temperatures of -15ºC, January is the coolest period in Headingley. The warmest time of year is July, when you can experience averages of 20ºC throughout the day. Whatever the weather, you'll find plenty of things to keep you occupied here.
What is the top hotel for my holiday in Headingley?
Hampton Inn by Hilton Winnipeg Airport/Polo Park is an ideal base for an exciting getaway in Headingley, offering all the comforts and conveniences you need and more.
How do I get a cheap holiday to Headingley?
One of the simplest ways to save pounds (and time) is to bundle your bookings with Expedia. Flights, hotels, activities and hire cars — we've got it all. Select the combination that best fits you and see your savings pile up. Of course, holidays are never one-size-fits-all. That's why we offer more than 400 airlines and 321,000 properties worldwide, which lets you customise your Headingley holiday your way. Learn more about how you can save money on your holiday when you combine your hotel and flight bookings with Expedia.
What should I do on my Headingley holiday?
Make sure your holiday in Headingley is one to remember by taking in its most popular attractions. Polo Park, Outlet Collection Winnipeg, Assiniboine Park Zoo and Canadian Forces Base Winnipeg are a few of the things to put on your itinerary while you're in the area.
What is the best area to stay in when on holiday in Headingley?
There's so much to see in Headingley, so stay near its best sights and maximise your time sightseeing. BellMTS Iceplex is one place to add to your to-do list.
Do I need a visa for my Headingley holiday?
Visa requirements for Headingley vary depending on your nationality and the purpose of your visit. We recommend checking official government websites to determine if you need a visa for your holiday. This is also a good place to find the most up-to-date information, including details about application procedures or any supporting documentation that might be necessary. Enquire about your visa requirements in advance to ensure a travel experience that's hassle free. Also double-check to see that your passport is valid for a further six months from your return date.
What should I wear on my Headingley holiday?
Though everyone's personal style varies, it can be helpful to have some guidelines for what kind of clothes to wear during your holiday in Headingley. We recommend browsing social media before you leave to get inspiration for local fashion trends. Daytime temperatures in January, Headingley's coolest month, average around -15ºC. July marks this city's warmest month when average temperatures reach 20ºC. Our advice? Take the guesswork out of what to pack and check the local weather forecast.
What does an Expedia Headingley holiday include?
It comes down to what sort of getaway you're thinking about. Headingley holiday deals can include flights, hotels and car hires. You can mix and match to create the package that suits your needs. You can also add on activities and experiences after you've booked to pick up even bigger discounts. Expedia features different types of properties, with the most popular in Headingley including hotels and motels. With Expedia, you can expect the flexibility and freedom to personalise your holiday however you want.
Does Expedia offer Book Now, Pay Later Headingley holidays?
Expedia has partnered with online lender Klarna to make booking your next getaway a bit easier on the wallet. Paying by instalment means you can spread the costs of your dream holiday, leaving you with more cash to spend while you're travelling. Klarna has several payment plans to pick from, so you're sure to find something that suits your budget. Check out these flexible payment options:

  • Pay monthly holidays: If paying in multiple transactions is something that would work for you, Klarna can help. Paying in convenient monthly instalments will make your holiday dreams possible.
  • No-deposit holidays: When you want to jump on an unbeatable deal but don't have the full amount yet, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to secure your getaway.

Can I choose my airline with a Headingley Expedia holiday?
You can. Expedia has access to more than 400 airline partners across the globe, so choose the carrier that best fits your budget and travel needs.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.