Title: Headingley Vacation Home Rentals from CA $123: Search Top Private Vacation Homes for Rent | Expedia.ca

[Headingley Travel Guide](https://expedia.ca/Headingley.dx6145346)[Hotels in Headingley](https://expedia.ca/Headingley-Hotels.d6145346.Travel-Guide-Hotels)[Vacation Rentals in Headingley](https://expedia.ca/Headingley-Vacation-Rentals.d6145346.Travel-Guide-VacationRentals)[Flights to Headingley](https://expedia.ca/Cheap-Flights-To-Headingley.d6145346.Travel-Guide-Flights)[Headingley Car Rentals](https://expedia.ca/Car-Rentals-In-Headingley.d6145346.Car-Rental-Guide)[Headingley Vacation Packages](https://expedia.ca/Headingley.d6145346.Destination-Travel-Guides)

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# Headingley Vacation Rentals

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## Check prices for these dates

Next weekend

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6145346&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=6145346&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=6145346&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=6145346&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Headingley vacation homes

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/60000000/59860000/59859800/59859720/4beaced1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/60000000/59860000/59859800/59859720/65783a6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/60000000/59860000/59859800/59859720/5095f06d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/60000000/59860000/59859800/59859720/ab88f631.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in St. Vital

[](https://www.expedia.ca/Winnipeg-Hotels-2-Bedrooms-Basement-With-Separate-Entrance.h59859720.Hotel-Information)

10/10

Exceptional

(1)

"The basement apartment was very clean and in a very good location. She was very helpful when we needed something and we had a nice little vacation in Winnipeg."

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Sharon W.

CA $147

CA $216 total

includes taxes & fees

Jan 3 - Jan 4, 2026

[](https://www.expedia.ca/Winnipeg-Hotels-2-Bedrooms-Basement-With-Separate-Entrance.h59859720.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/122000000/121590000/121584900/121584816/w1086h720x0y4-34365978.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/122000000/121590000/121584900/121584816/w1082h724x4y0-dbe5793a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Oven, stovetop](https://images.trvl-media.com/lodging/122000000/121590000/121584900/121584816/dd7ac49d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/122000000/121590000/121584900/121584816/6a3473cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Fort Garry

[](https://www.expedia.ca/Winnipeg-Hotels-Lakeview-Walkout-Suite-Private-Entrance.h121584816.Hotel-Information)

CA $48

CA $123 total

includes taxes & fees

Jan 3 - Jan 4, 2026

[](https://www.expedia.ca/Winnipeg-Hotels-Lakeview-Walkout-Suite-Private-Entrance.h121584816.Hotel-Information)

![Fridge, microwave, stovetop, electric kettle](https://images.trvl-media.com/lodging/72000000/71660000/71654500/71654457/916ea993.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/72000000/71660000/71654500/71654457/49cfadb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/72000000/71660000/71654500/71654457/368c9012.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/72000000/71660000/71654500/71654457/f5ff62f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in St. Vital

[](https://www.expedia.ca/Winnipeg-Hotels-Private-Basement-Apartment-With-Separate-Entrance.h71654457.Hotel-Information)

10/10

Exceptional

(1)

"Perfect for a 1 night stay. Just passing through. "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Norman

CA $90

CA $153 total

includes taxes & fees

Jan 3 - Jan 4, 2026

[](https://www.expedia.ca/Winnipeg-Hotels-Private-Basement-Apartment-With-Separate-Entrance.h71654457.Hotel-Information)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119120000/119110600/119110543/7dd779ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119120000/119110600/119110543/77cf72bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, coffee/tea maker, electric kettle](https://images.trvl-media.com/lodging/120000000/119120000/119110600/119110543/bcc579d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119120000/119110600/119110543/60b5f50c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Fort Garry

[](https://www.expedia.ca/Winnipeg-Hotels-Cozy-Suite-Peaceful-Modern.h119110543.Hotel-Information)

9.6/10

Exceptional

(4)

"Clean and quiet quaint oasis that we stayed overnight while attending a Celebration of Life. Host was very helpful. Easy to get to from the airport. Exactly what we needed. No hassles and a restful sleep. "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Nadine M.

CA $63

CA $182 total

includes taxes & fees

Dec 31 - Jan 1, 2026

[](https://www.expedia.ca/Winnipeg-Hotels-Cozy-Suite-Peaceful-Modern.h119110543.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/120000000/119580000/119575900/119575871/5008ef79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119580000/119575900/119575871/534df104.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119580000/119575900/119575871/0286fb08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave](https://images.trvl-media.com/lodging/120000000/119580000/119575900/119575871/d5cab17e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in St. Vital

[](https://www.expedia.ca/Winnipeg-Hotels-Charming-Lower-Level-Private-Entrance-Suite.h119575871.Hotel-Information)

10/10

Exceptional

(1)

CA $73

CA $182 total

includes taxes & fees

Dec 31 - Jan 1, 2026

[](https://www.expedia.ca/Winnipeg-Hotels-Charming-Lower-Level-Private-Entrance-Suite.h119575871.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/112000000/112000000/111999600/111999556/fbb4ee0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/112000000/111999600/111999556/b60c1fb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/112000000/111999600/111999556/0ca548bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/112000000/111999600/111999556/470450e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Transcona

[](https://www.expedia.ca/Winnipeg-Hotels-Luxury-Home-Away-From-Home-With-Private-Entrance.h111999556.Hotel-Information)

8.6/10

Excellent

(4)

"Nice suite, clean and relatively new. some defects pointed out to the owner and very receptive of comments."

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Bill H.

CA $50

CA $160 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Winnipeg-Hotels-Luxury-Home-Away-From-Home-With-Private-Entrance.h111999556.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/121000000/120670000/120661800/120661728/1a8fbb5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/121000000/120670000/120661800/120661728/06812597.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120670000/120661800/120661728/2444ba08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/121000000/120670000/120661800/120661728/492786b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Lord Roberts

[](https://www.expedia.ca/Winnipeg-Hotels-St-Thereses-Nest-Your-Peaceful-Retreat-Minutes-From-The-Pulse-Of-The-City.h120661728.Hotel-Information)

10/10

Exceptional

(1)

"Check in was easy. Great location. Parking on street in front of house no problem. Kitchen had the basics. Tassimo made wonderful coffee. Beds comfortable but firm. Host was exceptionally attentive and accommodating. She was a blessing."

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Joanne S.

CA $180

CA $457 total

includes taxes & fees

Jan 13 - Jan 14, 2026

[](https://www.expedia.ca/Winnipeg-Hotels-St-Thereses-Nest-Your-Peaceful-Retreat-Minutes-From-The-Pulse-Of-The-City.h120661728.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/112000000/111250000/111244100/111244061/163958ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/112000000/111250000/111244100/111244061/48383b92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/112000000/111250000/111244100/111244061/8eaedb80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111250000/111244100/111244061/4646eb98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Fort Garry

[](https://www.expedia.ca/Winnipeg-Hotels-Private-2-Bedroom-Suite.h111244061.Hotel-Information)

9.2/10

Wonderful

(11)

"Thank you for a great stay. Check in was easy, the basement suite had all we needed. Excellent WiFi.New home and neighbourhood. Great place to stay. We would stay here again."

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Ellie

CA $75

CA $178 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Winnipeg-Hotels-Private-2-Bedroom-Suite.h111244061.Hotel-Information)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/112000000/111940000/111937800/111937735/fee9ade4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111940000/111937800/111937735/47713a27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/112000000/111940000/111937800/111937735/851cfb23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/112000000/111940000/111937800/111937735/1bee0194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in St. Vital

[](https://www.expedia.ca/Winnipeg-Hotels-Kelvistas-Suite.h111937735.Hotel-Information)

9.6/10

Exceptional

(11)

"This property was amazing would love to stay here again "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Oluwatimilehin

CA $65

CA $184 total

includes taxes & fees

Jan 2 - Jan 3, 2026

[](https://www.expedia.ca/Winnipeg-Hotels-Kelvistas-Suite.h111937735.Hotel-Information)

![Microwave, stovetop, dishwasher, coffee/tea maker](https://images.trvl-media.com/lodging/107000000/106750000/106748500/106748471/fb34ba05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/107000000/106750000/106748500/106748471/79659a4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, stovetop, dishwasher, coffee/tea maker](https://images.trvl-media.com/lodging/107000000/106750000/106748500/106748471/9b36ecdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer, towels, soap, toilet paper](https://images.trvl-media.com/lodging/107000000/106750000/106748500/106748471/00028bb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Fort Garry

[](https://www.expedia.ca/Winnipeg-Hotels-Separate-Entrance-Basement-Suite.h106748471.Hotel-Information)

8.4/10

Very good

(9)

"Very good services."

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Alabi A.

CA $92

CA $139 total

includes taxes & fees

Jan 12 - Jan 13, 2026

[](https://www.expedia.ca/Winnipeg-Hotels-Separate-Entrance-Basement-Suite.h106748471.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/124000000/123090000/123080100/123080087/fece9f52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/124000000/123090000/123080100/123080087/c1a9424d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/124000000/123090000/123080100/123080087/e3c57fc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/124000000/123090000/123080100/123080087/c34a248a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Transcona

[](https://www.expedia.ca/Winnipeg-Hotels-Peaceful-Tyson-Trail-Retreat.h123080087.Hotel-Information)

CA $80

CA $160 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Winnipeg-Hotels-Peaceful-Tyson-Trail-Retreat.h123080087.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/113000000/112730000/112725600/112725598/f1dd098b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/113000000/112730000/112725600/112725598/9bf240d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/112730000/112725600/112725598/19236acd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, WiFi](https://images.trvl-media.com/lodging/113000000/112730000/112725600/112725598/e9861702.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Central St. Boniface

[](https://www.expedia.ca/Winnipeg-Hotels-Stylish-Spacious-Minutes-From-Downtown.h112725598.Hotel-Information)

10/10

Exceptional

(3)

"Well stocked, spacious, and central. Glad I stayed here. "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Dale K.

CA $119

CA $265 total

includes taxes & fees

Jan 7 - Jan 8, 2026

[](https://www.expedia.ca/Winnipeg-Hotels-Stylish-Spacious-Minutes-From-Downtown.h112725598.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/114000000/113650000/113646100/113646033/39c91ece.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113650000/113646100/113646033/150e41f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, towels, toilet paper](https://images.trvl-media.com/lodging/114000000/113650000/113646100/113646033/cc42919b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113650000/113646100/113646033/6e5f1745.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Winnipeg

[](https://www.expedia.ca/Winnipeg-Hotels-Cozy-Haven-1-Bedroom-Suite-Close-To-Centre-Of-Winnipeg.h113646033.Hotel-Information)

10/10

Exceptional

(2)

"Would definitely stay here again if I’m ever in Winnipeg! "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Ashton P.

CA $77

CA $138 total

includes taxes & fees

Jan 2 - Jan 3, 2026

[](https://www.expedia.ca/Winnipeg-Hotels-Cozy-Haven-1-Bedroom-Suite-Close-To-Centre-Of-Winnipeg.h113646033.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112730000/112725600/112725572/b925f840.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/113000000/112730000/112725600/112725572/bdacb595.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/112730000/112725600/112725572/c2d3cb39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/113000000/112730000/112725600/112725572/fa0a5ff5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in King Edward

[](https://www.expedia.ca/Winnipeg-Hotels-Shop-Dine-Free-Parking-7-Min-To-Airport.h112725572.Hotel-Information)

10/10

Exceptional

(2)

"Newer development, clean, beautifully designed. Comforts of home. Host replies in a timely matter. Enjoyed my stay with no hassle. "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Lori

CA $181

CA $333 total

includes taxes & fees

Jan 3 - Jan 4, 2026

[](https://www.expedia.ca/Winnipeg-Hotels-Shop-Dine-Free-Parking-7-Min-To-Airport.h112725572.Hotel-Information)

![Smart TV, computer monitors](https://images.trvl-media.com/lodging/116000000/115210000/115207400/115207316/92180034.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/116000000/115210000/115207400/115207316/9a0c261c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/116000000/115210000/115207400/115207316/3d5992f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/116000000/115210000/115207400/115207316/8c8d339f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in East Kildonan

[](https://www.expedia.ca/Winnipeg-Hotels-One-Bedroom-Guest-Suite-With-Private-Entry.h115207316.Hotel-Information)

10/10

Exceptional

(6)

"Cute, clean basement suite in a quiet neighborhood. Little out of the way of amenities but easily accessible if one has a vehicle. Will stay again if ever in town and in the area"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Devo A.

CA $65

CA $125 total

includes taxes & fees

Jan 2 - Jan 3, 2026

[](https://www.expedia.ca/Winnipeg-Hotels-One-Bedroom-Guest-Suite-With-Private-Entry.h115207316.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/112000000/112000000/111995700/111995692/99bf6871.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/112000000/112000000/111995700/111995692/75f4dd30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/112000000/112000000/111995700/111995692/f8d17135.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/112000000/111995700/111995692/276ac83e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Fort Garry

[](https://www.expedia.ca/Winnipeg-Hotels-Prairie-Luxury-2-Bedrooms-Home.h111995692.Hotel-Information)

9.4/10

Exceptional

(6)

"Great space. Host was very responsive to our requests."

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Bels45

CA $85

CA $302 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Winnipeg-Hotels-Prairie-Luxury-2-Bedrooms-Home.h111995692.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/122000000/121670000/121663800/121663743/145ee64e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121670000/121663800/121663743/335fe46d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121670000/121663800/121663743/7e4dfdc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/122000000/121670000/121663800/121663743/f4cac3d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Transcona

[](https://www.expedia.ca/Winnipeg-Hotels-Cozy-3-Bedroom-Basement-Suite-With-Private-Entrance.h121663743.Hotel-Information)

CA $80

CA $255 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Winnipeg-Hotels-Cozy-3-Bedroom-Basement-Suite-With-Private-Entrance.h121663743.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/123000000/122130000/122127000/122126932/c7b0fbc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122130000/122127000/122126932/w1434h959x0y0-13fe51a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122130000/122127000/122126932/62181924.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122130000/122127000/122126932/a258660a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Deer Lodge

[](https://www.expedia.ca/Winnipeg-Hotels-Spacious-New-3BR.h122126932.Hotel-Information)

CA $76

CA $267 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Winnipeg-Hotels-Spacious-New-3BR.h122126932.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96870000/96863600/96863544/e00f2a63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96870000/96863600/96863544/cc12833d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/97000000/96870000/96863600/96863544/6bd2a804.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/97000000/96870000/96863600/96863544/08b53467.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Norwood East

[](https://www.expedia.ca/Winnipeg-Hotels-New-Modern-Home-Free-Parking-5-Mins-Downtown.h96863544.Hotel-Information)

9.8/10

Exceptional

(6)

"Great place"

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Blaine

CA $125

CA $285 total

includes taxes & fees

Jan 25 - Jan 26, 2026

[](https://www.expedia.ca/Winnipeg-Hotels-New-Modern-Home-Free-Parking-5-Mins-Downtown.h96863544.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/84000000/83350000/83346200/83346181/685f2318.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83350000/83346200/83346181/2fd5af5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/84000000/83350000/83346200/83346181/9d66aec0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83350000/83346200/83346181/2be08485.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Weston

[](https://www.expedia.ca/Winnipeg-Hotels-Modern-3-Bedroom-Home-Wstreet-Parkn-Close-To.h83346181.Hotel-Information)

10/10

Exceptional

(3)

"This property is beautiful. The owner is top hostess she went above and beyond for us. Will definitely being staying here again"

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Aldeana L.

CA $155

CA $745 total

includes taxes & fees

Dec 31 - Jan 1, 2026

[](https://www.expedia.ca/Winnipeg-Hotels-Modern-3-Bedroom-Home-Wstreet-Parkn-Close-To.h83346181.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-01-13&endDate=2026-01-14&regionId=6145346&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Headingley%2C+Manitoba%2C+Canada&regionId=6145346&latLong=49.868087%2C-97.391052&adults=2&startDate=2026-03-29&d1=2026-03-29&endDate=2026-04-01&d2=2026-04-01&lodging=VACATION_HOME)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Headingley%2C+Manitoba%2C+Canada&regionId=6145346&latLong=49.868087%2C-97.391052&adults=2&startDate=2026-03-29&d1=2026-03-29&endDate=2026-04-01&d2=2026-04-01&lodging=APARTMENT)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Headingley%2C+Manitoba%2C+Canada&regionId=6145346&latLong=49.868087%2C-97.391052&adults=2&startDate=2026-03-29&d1=2026-03-29&endDate=2026-04-01&d2=2026-04-01&lodging=CONDO)

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## Top Headingley Hotel Reviews

![Lakeview Signature, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/470000/460400/460383/59de39cd_y.jpg)

### Lakeview Signature, Trademark Collection by Wyndham

10/10 Excellent

"Check in was quick and efficient, room was dated but very comfortable, diner in the restaurant was good, services well. All positives from my point of view."

[](https://expedia.ca/Winnipeg-Hotels-Lakeview-Signature.h460383.Hotel-Information)

![Motel 6 Headingley, MB - Winnipeg West](https://images.trvl-media.com/lodging/5000000/4470000/4464100/4464039/56e2f620_y.jpg)

### Motel 6 Headingley, MB - Winnipeg West

10/10 Excellent

"Room was clean! staff was great!"

[](https://expedia.ca/Winnipeg-Hotels-Motel-6-Headingley.h4464039.Hotel-Information)

![Super 8 by Wyndham Winnipeg East MB](https://images.trvl-media.com/lodging/1000000/910000/906400/906335/1f53b81c_y.jpg)

### Super 8 by Wyndham Winnipeg East MB

10/10 Excellent

"Staff friendly love the shower. Good breakfast. "

[](https://expedia.ca/Winnipeg-Hotels-Super-8-By-Wyndham-Winnipeg-East-MB.h906335.Hotel-Information)

![The Grand Winnipeg Airport Hotel by Lakeview](https://images.trvl-media.com/lodging/8000000/7720000/7719900/7719845/cc015fce_y.jpg)

### The Grand Winnipeg Airport Hotel by Lakeview

10/10 Excellent

"Great "

[](https://expedia.ca/Winnipeg-Hotels-The-Grand-Winnipeg-Airport-Hotel-By-Lakeview.h7719845.Hotel-Information)

![Victoria Inn Hotel and Convention Centre Winnipeg](https://images.trvl-media.com/lodging/1000000/20000/13300/13226/94dbadb8_y.jpg)

### Victoria Inn Hotel and Convention Centre Winnipeg

10/10 Excellent

"Short stay, room was set fairly hot, even for winter but was easily corrected. Everything else was good, staff were friendly and helpful. "

[](https://expedia.ca/Winnipeg-Hotels-Victoria-Inn-Hotel-And-Convention-Centre-Winnipeg.h13226.Hotel-Information)

![Canad Inns Destination Centre Club Regent Casino Hotel](https://images.trvl-media.com/lodging/1000000/590000/583700/583630/c7554b08_y.jpg)

### Canad Inns Destination Centre Club Regent Casino Hotel

10/10 Excellent

"Always enjoy staying here!"

[](https://expedia.ca/Winnipeg-Hotels-Canad-Inns-Destination-Centre-Club-Regent-Casino-Hotel.h583630.Hotel-Information)

![Radisson Hotel Winnipeg Downtown](https://images.trvl-media.com/lodging/1000000/530000/524400/524375/9d4fad4b_y.jpg)

### Radisson Hotel Winnipeg Downtown

10/10 Excellent

"Excellent "

[](https://expedia.ca/Winnipeg-Hotels-Radisson-Hotel-Winnipeg-Downtown.h524375.Hotel-Information)

![Travelodge by Wyndham Winnipeg East](https://images.trvl-media.com/lodging/1000000/870000/862700/862691/12af28ee_y.jpg)

### Travelodge by Wyndham Winnipeg East

10/10 Excellent

"Great breakfast. Pet friendly. "

[](https://expedia.ca/Winnipeg-Hotels-Travelodge-By-Wyndham-Winnipeg-East.h862691.Hotel-Information)

![The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/40000/34100/34086/8ffbe4a7_y.jpg)

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

10/10 Excellent

"Another Excellent stay at the Fort Garry"

[](https://expedia.ca/Winnipeg-Hotels-The-Fort-Garry-Hotel.h34086.Hotel-Information)

## Find out more about Headingley

## Headingley Vacation Homes information

| Number of reviews | 61                 |
| ----------------- | ------------------ |
| Accommodation     | 240 Vacation Homes |
| Lowest Price      | CA $123            |
| Highest Price     | CA $745            |

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- [Flights to Winnipeg ](https://www.expedia.ca/Cheap-Flights-To-Winnipeg.d6141041.Travel-Guide-Flights)
- [Flights from Winnipeg James Armstrong Richardson Intl. ](https://www.expedia.ca/lp/airports/ywg/flights-from-winnipeg-james-armstrong-richardson-intl-airport)
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- [Flights from Delhi (DEL) to Winnipeg (YWG) ](https://www.expedia.ca/lp/flights/del/ywg/delhi-to-winnipeg)
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- [Flights from Ottawa (YOW) to Winnipeg (YWG) ](https://www.expedia.ca/lp/flights/yow/ywg/ottawa-to-winnipeg)
- [Flights from Regina (YQR) to Winnipeg (YWG) ](https://www.expedia.ca/lp/flights/yqr/ywg/regina-to-winnipeg)
- [Flights from Thunder Bay (YQT) to Winnipeg (YWG) ](https://www.expedia.ca/lp/flights/yqt/ywg/thunder-bay-to-winnipeg)
- [Flights from Montreal (YUL) to Winnipeg (YWG) ](https://www.expedia.ca/lp/flights/yul/ywg/montreal-to-winnipeg)
- [Flights from Vancouver (YVR) to Winnipeg (YWG) ](https://www.expedia.ca/lp/flights/yvr/ywg/vancouver-to-winnipeg)
- [Flights from Saskatoon (YXE) to Winnipeg (YWG) ](https://www.expedia.ca/lp/flights/yxe/ywg/saskatoon-to-winnipeg)
- [Flights from Abbotsford (YXX) to Winnipeg (YWG) ](https://www.expedia.ca/lp/flights/yxx/ywg/abbotsford-to-winnipeg)
- [Flights from Calgary (YYC) to Winnipeg (YWG) ](https://www.expedia.ca/lp/flights/yyc/ywg/calgary-to-winnipeg)
- [Flights from Toronto (YYZ) to Winnipeg (YWG) ](https://www.expedia.ca/lp/flights/yyz/ywg/toronto-to-winnipeg)

- [Assiniboia Downs ](https://www.expedia.ca/Assiniboia-Downs-Winnipeg.d6229713.Vacation-Attraction)
- [Beaudry Provincial Park ](https://www.expedia.ca/Beaudry-Provincial-Park-Manitoba.d6255869.Vacation-Attraction)
- [Glendale Golf and Country Club ](https://www.expedia.ca/Glendale-Golf-And-Country-Club-Glendale.d6194090.Vacation-Attraction)
- [Grant's Old Mill Museum ](https://www.expedia.ca/Grants-Old-Mill-Museum-Winnipeg.d553248621561214609.Vacation-Attraction)
- [John Blumberg Softball Complex ](https://www.expedia.ca/John-Blumberg-Softball-Complex-Headingley.d6255853.Vacation-Attraction)
- [Red River Exhibition Park ](https://www.expedia.ca/Red-River-Exhibition-Park-Buchanan.d6229627.Vacation-Attraction)
- [Thunder Rapids Fun Park ](https://www.expedia.ca/Thunder-Rapids-Fun-Park-Headingley.d553248621561234992.Vacation-Attraction)
- [Unicity Mall ](https://www.expedia.ca/Unicity-Mall-Winnipeg.d553248621585428171.Vacation-Attraction)
- [Visit Westdale ](https://www.expedia.ca/Winnipeg-Westdale.dx873292502896168960)

- [Car rentals near Academy Lanes West ](https://www.expedia.ca/Car-Rentals-In-Academy-Lanes-West.d642299788980453376.Car-Rental-Guide)
- [Rental cars Winnipeg James Armstrong Richardson Intl. airport ](https://www.expedia.ca/Car-Rentals-In-Winnipeg-James-Armstrong-Richardson-Intl.d4675417.Car-Rental-Guide)
- [Car rentals near Winnipeg ](https://www.expedia.ca/Car-Rentals-In-Winnipeg.d6141041.Car-Rental-Guide)

- [Things to do in Winnipeg ](https://www.expedia.ca/Things-To-Do-In-Winnipeg.d6141041.Travel-Guide-Activities)