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

1. The Abode family space

The Abode family space
Fort Garry
The price is NZ$337
includes taxes & fees
15 Oct - 16 Oct
The Abode family space

2. Prairie Luxury 1 Bedrooms Home

Prairie Luxury 1 Bedrooms Home
Fort Garry
9.2 out of 10, Wonderful, (12 reviews)
"Wonderful stay! Clean and comfortable. Great hosts. I would definitely stay again. "
Canada
Carol M.
The price is NZ$296
includes taxes & fees
10 Oct - 11 Oct
Prairie Luxury 1 Bedrooms Home

3. Canada Life Centre° Osborne Location

Canada Life Centre° Osborne Location
Osborne Village
9.8 out of 10, Exceptional, (7 reviews)
"Perfect stay for 5 nights with my daughter. I would stay here again. "
Canada
Billie F.
The price is NZ$254
includes taxes & fees
13 Oct - 14 Oct
Canada Life Centre° Osborne Location

4. One-bedroom guest suite with private entry

One-bedroom guest suite with private entry
East Kildonan
9.4 out of 10, Exceptional, (11 reviews)
"The suite was spacious and well equipped."
United States
Michael G.
The price is NZ$176
includes taxes & fees
14 Oct - 15 Oct
One-bedroom guest suite with private entry

5. Golden Eagle, Basement Suite

Golden Eagle, Basement Suite
Winnipeg
9.0 out of 10, Wonderful, (17 reviews)
"Nice place liked to stay"
Canada
Simran K.
The price is NZ$256
includes taxes & fees
13 Oct - 14 Oct
Golden Eagle, Basement Suite

6. 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 NZ$206
includes taxes & fees
11 Oct - 12 Oct
Separate Entrance Basement Suite

7. The Peaceful Lower Loft Where Comfort Meets Quiet Escape.

The Peaceful Lower Loft Where Comfort Meets Quiet Escape.
Fort Garry
10.0 out of 10, Exceptional, (2 reviews)
"Full privacy, had a peaceful stay. I highly recommend if anyone is looking for a quiet peaceful stay."
Canada
Vijaya Shree
The price is NZ$182
includes taxes & fees
2 Nov - 3 Nov
The Peaceful Lower Loft Where Comfort Meets Quiet Escape.

8. The Cozy Corner Home

The Cozy Corner Home
2.0 star property
East Kildonan
The price is NZ$179
includes taxes & fees
12 Oct - 13 Oct
The Cozy Corner Home

9. Stormwater Haven: Peaceful, Stylish and comfortable space in South Winnipeg.

Stormwater Haven: Peaceful, Stylish and comfortable space in South Winnipeg.
Fort Garry
9.2 out of 10, Wonderful, (7 reviews)
"Overall, it was a decent unit. Central enough to all the places I needed to visit. My only complaint was that it was way too cold in the unit (despite the scorching heat outside) that I had to occasionally turn on the heating which kept leading to a power outage in the unit."
Canada
Kester
The price is NZ$193
includes taxes & fees
9 Oct - 10 Oct
Stormwater Haven: Peaceful, Stylish and comfortable space in South Winnipeg.

10. 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 NZ$199
includes taxes & fees
9 Oct - 10 Oct
Duniques unique home Fully furnished 2 bedroom basement suite

11. FREE PARKING NY Style Condo in Exchange District

FREE PARKING NY Style Condo in Exchange District
Exchange District
10.0 out of 10, Exceptional, (95 reviews)
"Lovely stay - very spacious, secure and clean! Would recommend"
Canada
Alyssa
The price is NZ$277
includes taxes & fees
15 Oct - 16 Oct
FREE PARKING NY Style Condo in Exchange District

12. Home away from home! Entire basement suite with privacy and driveway parking!

Home away from home! Entire basement suite with privacy and driveway parking!
Fort Garry
10.0 out of 10, Exceptional, (3 reviews)
"very clean, lovely space. loved staying for our anniversary "
Canada
Rayna
The price is NZ$207
includes taxes & fees
12 Oct - 13 Oct
Home away from home! Entire basement suite with privacy and driveway parking!

13. Peaceful and spacious one bed and rec-room for short or long stay

Peaceful and spacious one bed and rec-room for short or long stay
Fort Garry
The price is NZ$220
includes taxes & fees
10 Oct - 11 Oct
Peaceful and spacious one bed and rec-room for short or long stay

14. Welcoming Private 2 Bedroom Suite

Welcoming Private 2 Bedroom Suite
Fort Garry
9.6 out of 10, Exceptional, (17 reviews)
"Clean area, nice peaceful area."
Canada
Vince
The price is NZ$226
includes taxes & fees
11 Oct - 12 Oct
Welcoming Private 2 Bedroom Suite

15. Cozy Haven 1-bedroom suite close to centre of Winnipeg

Cozy Haven 1-bedroom suite close to centre of Winnipeg
Winnipeg
8.6 out of 10, Excellent, (4 reviews)
"Would definitely stay here again if I’m ever in Winnipeg! "
Canada
Ashton P.
The price is NZ$187
includes taxes & fees
31 Oct - 1 Nov
Cozy Haven 1-bedroom suite close to centre of Winnipeg

16. Private Cozy 1 Bedroom Basement Suite

Private Cozy 1 Bedroom Basement Suite
Fort Garry
9.4 out of 10, Exceptional, (6 reviews)
"Nice clean place to stay"
United States
Thomas B.
The price is NZ$219
includes taxes & fees
12 Oct - 13 Oct
Private Cozy 1 Bedroom Basement Suite

17. HOME AWAY FROM HOME

HOME AWAY FROM HOME
Fort Garry
9.6 out of 10, Exceptional, (4 reviews)
"Worked well for us"
United States
Diane C.
The price is NZ$285
includes taxes & fees
10 Oct - 11 Oct
HOME AWAY FROM HOME

18. The Wooden Nest | Your Comfy Relaxing Escape

The Wooden Nest | Your Comfy Relaxing Escape
King Edward
9.6 out of 10, Exceptional, (18 reviews)
"I had a very pleasant stay. The place was clean, comfortable, and well located. I truly enjoyed my stay and would definitely recommend it.”"
Canada
Alyson J.
The price is NZ$482
includes taxes & fees
12 Oct - 13 Oct
The Wooden Nest | Your Comfy Relaxing Escape

19. Maryland Homestay - Downtown Apartment #1

Maryland Homestay - Downtown Apartment #1
Winnipeg
8.0 out of 10, Very good, (7 reviews)
"Yes, you can walk to get everything you need. "
Canada
Allen
The price is NZ$220
includes taxes & fees
12 Oct - 13 Oct
Maryland Homestay - Downtown Apartment #1

20. Cozy 2BR Suite • Private Entry • Free Parking• self check-in

Cozy 2BR Suite • Private Entry • Free Parking• self check-in
Peguis
The price is NZ$238
includes taxes & fees
9 Oct - 10 Oct
Cozy 2BR Suite • Private Entry • Free Parking• self check-in
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Headingley holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Headingley. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Headingley. Seeing all the best attractions is bound to make you fall in love with Headingley. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Headingley short-term rentals, that won’t be hard to do.

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?

St B. Living : This holiday home rental outside of Headingley is equipped with a balcony, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, 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.