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

Headingley Holiday Rentals

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Our top choices for Headingley holiday rentals

The Guest Expertise – Where Elegance Meets Comfort in a 5BR Luxury Retreat

The Guest Expertise – Where Elegance Meets Comfort in a 5BR Luxury Retreat
Winnipeg
10.0 out of 10, Exceptional, (3 reviews)
"This property suited us well for a business meeting to the city! Very nice neighborhood "
Canada
Marilee K.
The price is AU$539
includes taxes & fees
3 Aug - 4 Aug
The Guest Expertise – Where Elegance Meets Comfort in a 5BR Luxury Retreat

Separate Entrance Basement Suite

Separate Entrance Basement Suite
Fort Garry
8.0 out of 10, Very good, (11 reviews)
"Very clean beautiful place. Very comfy for a great price would recommend "
United States
Addy F.
The price is AU$170
includes taxes & fees
3 Aug - 4 Aug
Separate Entrance Basement Suite

Modern 3BR Home near Airport & PoloPark | Sleeps 8

Modern 3BR Home near Airport & PoloPark | Sleeps 8
King Edward
9.2 out of 10, Wonderful, (26 reviews)
"Perfect 👌"
Canada
Paola
The price is AU$388
includes taxes & fees
27 July - 28 July
Modern 3BR Home near Airport & PoloPark | Sleeps 8

HOME AWAY FROM HOME

HOME AWAY FROM HOME
Fort Garry
10.0 out of 10, Exceptional, (3 reviews)
"This apartment was perfect for the two of us! Nice, clean and the bed was incredibly comfortable! Easy check in and check out! "
Canada
Tania
The price is AU$233
includes taxes & fees
26 July - 27 July
HOME AWAY FROM HOME

Cozy Stay Near Airport|Bright, Clean and Peaceful!

Cozy Stay Near Airport|Bright, Clean and Peaceful!
King Edward
9.6 out of 10, Exceptional, (14 reviews)
"Clean house, comfortable beds, great location!"
Canada
Travis
Cozy Stay Near Airport|Bright, Clean and Peaceful!

Prime Location | Near Airport & Shopping Malls

Prime Location | Near Airport & Shopping Malls
King Edward
9.4 out of 10, Exceptional, (3 reviews)
"Comfortable, clean and conveniently located to the airport. "
Canada
Andrea A.
Prime Location | Near Airport & Shopping Malls

Perfect Comfy Retreat | Premium Location Home Stay

Perfect Comfy Retreat | Premium Location Home Stay
King Edward
8.8 out of 10, Excellent, (3 reviews)
"Great place to stay. Great amenities, clean and spacious and host was very accommodating. "
United States
Tammy M.
The price is AU$472
includes taxes & fees
23 July - 24 July
Perfect Comfy Retreat | Premium Location Home Stay

Spacious new 3 Bedroom, sleeps 10, King Bed, 8min to YWG

Spacious new 3 Bedroom, sleeps 10, King Bed, 8min to YWG
Deer Lodge
The price is AU$379
includes taxes & fees
3 Aug - 4 Aug
Spacious new 3 Bedroom, sleeps 10, King Bed, 8min to YWG

*Spacious w/ Style | Free Parking | 7 min Airport*

*Spacious w/ Style | Free Parking | 7 min Airport*
King Edward
9.6 out of 10, Exceptional, (9 reviews)
"This location was easy to get to, incredibly clean and had everything we needed. We had a great stay and will definitely come again!"
United States
Julie R.
The price is AU$439
includes taxes & fees
28 July - 29 July
*Spacious w/ Style | Free Parking | 7 min Airport*

Luxury Tuxedo Family Home with Hot Tub

Luxury Tuxedo Family Home with Hot Tub
Tuxedo
9.8 out of 10, Exceptional, (47 reviews)
"Our stay was great and hosts were wonderful. "
Canada
sharla m.
The price is AU$1,031
includes taxes & fees
19 Aug - 20 Aug
Luxury Tuxedo Family Home with Hot Tub

Duniques unique home Fully furnished 2 bedroom basement suite

Duniques unique home Fully furnished 2 bedroom basement suite
Fort Garry
8.0 out of 10, Very good, (1 review)
"Very nice quiet place to stay."
Canada
Lisa W.
The price is AU$161
includes taxes & fees
3 Aug - 4 Aug
Duniques unique home Fully furnished 2 bedroom basement suite

Prairie Luxury 1 Bedrooms Home

Prairie Luxury 1 Bedrooms Home
Fort Garry
9.4 out of 10, Exceptional, (8 reviews)
"Enjoyed my 3 night stay very much here! The property was exceptionally clean and modern! It was also very easy to communicate with the owner regarding check in and check out rules! Great and safe location."
Canada
Emma
The price is AU$246
includes taxes & fees
28 July - 29 July
Prairie Luxury 1 Bedrooms Home

Canada Life Centre° Osborne Location

Canada Life Centre° Osborne Location
Osborne Village
9.6 out of 10, Exceptional, (5 reviews)
"The location is very good! It is in Osborne area but not at Canada life centre. It was a very good size and well furnished!"
Canada
Celine
The price is AU$221
includes taxes & fees
7 Aug - 8 Aug
Canada Life Centre° Osborne Location

Private Suite | Prairie Pointe & Near UofM

Private Suite | Prairie Pointe & Near UofM
Fort Garry
9.8 out of 10, Exceptional, (6 reviews)
"Great little suite, host was very pleasant and accommodating. Quiet, comfortable, would stay here again 100%."
Canada
Melissa D.
The price is AU$140
includes taxes & fees
3 Aug - 4 Aug
Private Suite | Prairie Pointe & Near UofM

FREE PARKING NY Style Condo in Exchange District

FREE PARKING NY Style Condo in Exchange District
Exchange District
10.0 out of 10, Exceptional, (88 reviews)
"Property was exactly as listed, clean, comfortable and well located. Excellent stay and would definately stay her again"
Canada
Jackie
The price is AU$235
includes taxes & fees
28 July - 29 July
FREE PARKING NY Style Condo in Exchange District

Spacious 1 Bed/1 Bath near HSC and Downtown *Sleeps 4 and Free Parking

Spacious 1 Bed/1 Bath near HSC and Downtown *Sleeps 4 and Free Parking
West Alexander
10.0 out of 10, Exceptional, (1 review)
"This was a perfect location if you have appointments at the Health Sciences Center. 5-10min walk to the William Street Entrance. Quiet location, comfortable apartment."
Canada
Jennifer
The price is AU$291
includes taxes & fees
3 Aug - 4 Aug
Spacious 1 Bed/1 Bath near HSC and Downtown *Sleeps 4 and Free Parking

Northside Comfort! Pet Friendly Budget Rental close to HSC and The Forks!!!

Northside Comfort! Pet Friendly Budget Rental close to HSC and The Forks!!!
Winnipeg
10.0 out of 10, Exceptional, (1 review)
"I liked most things with this property. We were a bit worried about the location as it was in a less than desirable neighbourhood. Having said that, the manager was wonderful and always willing to help. The neighbours across the road were friendly and helpful. There are security cameras and lots of light so coming home late was not an issue. All in all, I believe we got a fair and good deal."
Canada
Brenda
The price is AU$277
includes taxes & fees
22 July - 23 July
Northside Comfort! Pet Friendly Budget Rental close to HSC and The Forks!!!

Modern 2 Bedroom Home In A Prime Location

Modern 2 Bedroom Home In A Prime Location
Winnipeg
The price is AU$380
includes taxes & fees
3 Aug - 4 Aug
Modern 2 Bedroom Home In A Prime Location

Mary's Luxury Suite

Mary's Luxury Suite
Fort Garry
9.0 out of 10, Wonderful, (2 reviews)
"It was great and wanted to apologize for the in and out, my son vapes so he kelp going in and out. I wasn’t sure which door you were referring to, to leave open. Had a great sleep! And Saskatchewan won so we were happy! Thank you! "
Canada
Patricia S.
The price is AU$239
includes taxes & fees
3 Aug - 4 Aug
Mary's Luxury Suite

*1min Riverview Health 7min Downtown Free Parking

*1min Riverview Health 7min Downtown Free Parking
Winnipeg
9.0 out of 10, Wonderful, (12 reviews)
"Host very helpful. Quick to respond and sort out any issues.Amenities were fantastic."
United States
osayimwense o.
The price is AU$356
includes taxes & fees
22 July - 23 July
*1min Riverview Health 7min Downtown Free Parking
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.
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Top Headingley Hotel Reviews

Find out more about Headingley

Everything you need to know about Headingley holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Headingley holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Headingley holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Headingley holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Headingley. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Headingley holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Headingley holiday rentals we have selected for you start as low as AU$149 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Headingley rentals

At Expedia, we put the best Headingley holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Headingley rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Headingley holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Headingley. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Headingley?

Yes, there are holiday rentals in Headingley close to Thunder Rapids Fun Park, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Headingley has a good selection of coffee shops. Make sure you have time to check out the hockey games and riverfront during your trip.

What are some of the best holiday rentals that Headingley has to offer?

Brilliant 4-bedroom house with AC in Winnipeg: This holiday home rental outside of Headingley offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family.

What can I see and do in Headingley?

While exploring the area, visit family-friendly sights like Thunder Rapids Fun Park, or get outside and enjoy nature at Assiniboine Park. While here, John Blumberg Golf Course and John Blumberg Softball Complex are other places worth a visit.

What are holiday rentals like in Headingley?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Headingley. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from public hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for families.