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

Headingley Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Headingley vacation rentals

A two-story house with a grey garage door, a covered driveway, and a wooden fence in the background.

1. 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 ￥7,103
￥23,959 total
includes taxes & fees
Nov 3 - Nov 4
Prairie Luxury 1 Bedrooms Home
A residential exterior with a wooden gate, a concrete step leading to a door, and a welcome mat.

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

The Peaceful Lower Loft Where Comfort Meets Quiet Escape.
Fort Garry
9.4 out of 10, Exceptional, (3 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 ￥8,829
￥12,951 total
includes taxes & fees
Nov 16 - Nov 17
The Peaceful Lower Loft Where Comfort Meets Quiet Escape.
A modern two-story building with a concrete staircase leading to a white door marked with the number 474.

3. The Cozy Corner Home

The Cozy Corner Home
2.0 star property
East Kildonan
The price is ￥13,221
￥18,614 total
includes taxes & fees
Nov 15 - Nov 16
The Cozy Corner Home
A modern lobby with leather sofas, a glass coffee table, and abstract wall art.

4. Cozy 1 Bedroom Apt In Heart Of Downtown Winnipeg

Cozy 1 Bedroom Apt In Heart Of Downtown Winnipeg
Downtown Winnipeg
9.6 out of 10, Exceptional, (20 reviews)
"Clean and easy to access"
Canada
Tina
The price is ￥13,733
￥20,087 total
includes taxes & fees
Nov 8 - Nov 9
Cozy 1 Bedroom Apt In Heart Of Downtown Winnipeg
Private kitchen

5. The Abode family space

The Abode family space
Fort Garry
The price is ￥13,530
￥28,824 total
includes taxes & fees
Nov 10 - Nov 11
The Abode family space
A modern living room with a leather sofa set, a glass coffee table, and a lamp.

6. 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 ￥10,148
￥22,822 total
includes taxes & fees
Nov 5 - Nov 6
Canada Life Centre° Osborne Location
A residential driveway with a circular brick pattern leading to a garage.

7. Golden Eagle, Basement Suite

Golden Eagle, Basement Suite
Winnipeg
9.2 out of 10, Wonderful, (20 reviews)
"It was a great stay! Quiet and comfortable, host was always nice."
United States
nathalie
The price is ￥9,020
￥20,099 total
includes taxes & fees
Nov 3 - Nov 4
Golden Eagle, Basement Suite
A modern interior with a wooden staircase, a dining area with a chandelier, and a white cabinet.

8. Upscale Tuxedo Family Retreat with Hot Tub

Upscale Tuxedo Family Retreat with Hot Tub
Tuxedo
9.8 out of 10, Exceptional, (48 reviews)
"Great house in a great location! Host was very responsive. Would highly recommend!"
United States
Kayla G.
The price is ￥54,087
￥121,255 total
includes taxes & fees
Nov 9 - Nov 10
Upscale Tuxedo Family Retreat with Hot Tub
A modern kitchen with a central island, a dining area with a table and chairs, and a living room with a sofa and a TV.

9. Modern 3bedroom with ensuite bathrooms Lakeview home in Prairie Pointe, winnipeg

Modern 3bedroom with ensuite bathrooms Lakeview home in Prairie Pointe, winnipeg
Fort Garry
9.4 out of 10, Exceptional, (3 reviews)
"Clean and spacious."
United States
Reuben S.
The price is ￥30,443
￥70,410 total
includes taxes & fees
Nov 3 - Nov 4
Modern 3bedroom with ensuite bathrooms Lakeview home in Prairie Pointe, winnipeg
A kitchen with white cabinets, a marble backsplash, and three abstract paintings on the wall.

10. Cozy 2-Bedroom Home in St-Boniface – 5 Min Walk to Food, Fuel & More

Cozy 2-Bedroom Home in St-Boniface – 5 Min Walk to Food, Fuel & More
Central St. Boniface
8.6 out of 10, Excellent, (19 reviews)
"A great space - nice and clean and bright unit and with off street parking which was great. The unit was well-equipped with everything I needed and very comfy mattress. Deo was a great host - quick to respond and friendly and went out of his way to resolve a small problem I created! Tne location is great too.I'd definitely stay here again!"
United States
Jordanna C.
The price is ￥10,148
￥16,638 total
includes taxes & fees
Nov 3 - Nov 4
Cozy 2-Bedroom Home in St-Boniface – 5 Min Walk to Food, Fuel & More
A room with two white upholstered chairs, a dark carpet, and large windows with a view of trees and buildings.

11. Retraite Saint Boniface/St. Boniface Retreat

Retraite Saint Boniface/St. Boniface Retreat
Central St. Boniface
9.2 out of 10, Wonderful, (12 reviews)
"Great neighborhood and great place to stay "
Canada
jenn
The price is ￥16,913
￥30,158 total
includes taxes & fees
Nov 12 - Nov 13
Retraite Saint Boniface/St. Boniface Retreat
A modern conference room with a glass table, black chairs, a large flat-screen TV, and a decorative plant.

12. 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 ￥8,456
￥17,971 total
includes taxes & fees
Nov 3 - Nov 4
Welcoming Private 2 Bedroom Suite
A living room with a flat-screen TV, a sofa, a dining table, and a plant.

13. HOME AWAY FROM HOME

HOME AWAY FROM HOME
Fort Garry
9.2 out of 10, Wonderful, (5 reviews)
"Worked well for us"
United States
Diane C.
The price is ￥10,711
￥20,099 total
includes taxes & fees
Nov 3 - Nov 4
HOME AWAY FROM HOME
A spacious indoor area with high ceilings, exposed brick walls, and a central wooden table.

14. FREE PARKING NY Style Condo in Exchange District

FREE PARKING NY Style Condo in Exchange District
Exchange District
10.0 out of 10, Exceptional, (96 reviews)
"Lovely stay - very spacious, secure and clean! Would recommend"
Canada
Alyssa
The price is ￥11,568
￥23,568 total
includes taxes & fees
Nov 5 - Nov 6
FREE PARKING NY Style Condo in Exchange District
A hotel room with a bed, a desk, a chair, a lamp, a TV, and a window with curtains.

15. Affordable Bachelor Near HSC & Downtown

Affordable Bachelor Near HSC & Downtown
West Alexander
8.0 out of 10, Very good, (1 review)
"No bathtub. Parking was a headache as others kept parking in my spot."
Canada
MARIO
The price is ￥7,509
￥21,701 total
includes taxes & fees
Nov 13 - Nov 14
Affordable Bachelor Near HSC & Downtown
A modern bedroom with a bed, a nightstand, a dresser, and a window with blinds.

16. 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 ￥7,442
￥16,953 total
includes taxes & fees
Nov 17 - Nov 18
Home away from home! Entire basement suite with privacy and driveway parking!
A bedroom with a bed, a television displaying a movie, and a wardrobe.

17. Mary's Luxury Suite

Mary's Luxury Suite
Fort Garry
8.4 out of 10, Very good, (5 reviews)
"Good"
United States
kevin
The price is ￥11,275
￥24,822 total
includes taxes & fees
Nov 3 - Nov 4
Mary's Luxury Suite
A compact kitchen with a central island, a dining area with bar stools, and a black leather sofa.

18. Serene 3 Bed Room Near Airport/Polo Park Main Floor Bedroom

Serene 3 Bed Room Near Airport/Polo Park Main Floor Bedroom
Weston
9.2 out of 10, Wonderful, (5 reviews)
"It was so nice and quite, forgot I was in Winnipeg for a second"
Canada
Charmaine
The price is ￥15,785
￥29,491 total
includes taxes & fees
Nov 4 - Nov 5
Serene 3 Bed Room Near Airport/Polo Park Main Floor Bedroom
A resort with a central pool, wooden cabins, and a mountainous backdrop.

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

Spacious new 3 Bedroom, sleeps 10, King Bed, 8min to YWG
Deer Lodge
10.0 out of 10, Exceptional, (1 review)
"Beautiful property, got ready for my wedding with my bridesmaids and there was more than enough room for all 8 of us and 2 hair and 2 makeup girls!Would recommend"
Canada
Renee A.
The price is ￥22,598
￥44,923 total
includes taxes & fees
Nov 3 - Nov 4
Spacious new 3 Bedroom, sleeps 10, King Bed, 8min to YWG
A residential building with a stone facade, a front door, and a set of concrete steps leading to a driveway.

20. Clean and Comfortable Home

Clean and Comfortable Home
Fort Garry
The price is ￥6,799
￥15,526 total
includes taxes & fees
Nov 3 - Nov 4
Clean and Comfortable Home
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

Lakeview Signature, Trademark Collection by Wyndham

Lakeview Signature, Trademark Collection by Wyndham

10/10 Excellent
"Another great stay! Becoming my go to hotel."
Emily 1-night trip
Posted 3 hours ago
Lakeview Signature, Trademark Collection by Wyndham

Find out more about Headingley

Search for holiday rentals in Headingley on Expedia! You can easily find your home rentals, villas, holiday apartments in Headingley using one of the methods below:

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Look no further and take a look at our great range of rental properties in Headingley!

Frequently asked questions

Can I find a vacation rental in Headingley?

Yes, you can find vacation rentals in Headingley close to Thunder Rapids Fun Park, or you can go with a secluded option if you're looking for a relaxing stay. Our travelers say Headingley has a good selection of coffeehouses. Make sure you have time to check out the hockey games and riverfront during your trip.

What are some of the best vacation rentals in Headingley?

St B. Living : This vacation 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 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 vacation rentals like in Headingley?

Vacation rentals are privately owned properties you can book for a few days or a quick weekend in Headingley. Vacation rentals offer extras like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy front desks while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for a family getaway.