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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Our top choices for Headingley vacation homes

1. 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 CA $77
CA $128 total
includes taxes & fees
Nov 14 - Nov 15
Cozy Haven 1-bedroom suite close to centre of Winnipeg

2. Winnipeg Radiant Home - A peaceful neighborhood with separate entrance

Winnipeg Radiant Home - A peaceful neighborhood with separate entrance
East Kildonan
9.4 out of 10, Exceptional, (10 reviews)
"Clean and quiet. Perfect for an overnight before a flight."
Canada
Erika
The price is CA $67
CA $118 total
includes taxes & fees
Dec 1 - Dec 2
Winnipeg Radiant Home - A peaceful neighborhood with separate entrance

3. 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 CA $479
CA $1,115 total
includes taxes & fees
Nov 30 - Dec 1
Upscale Tuxedo Family Retreat with Hot Tub

4. 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 CA $63
CA $225 total
includes taxes & fees
Nov 14 - Nov 15
Prairie Luxury 1 Bedrooms Home

5. The Cozy Corner Home

The Cozy Corner Home
2.0 star property
East Kildonan
The price is CA $119
CA $167 total
includes taxes & fees
Nov 13 - Nov 14
The Cozy Corner Home

6. 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 CA $71
CA $128 total
includes taxes & fees
Nov 16 - Nov 17
One-bedroom guest suite with private entry

7. Welcoming Private 2 Bedroom Suite

Welcoming Private 2 Bedroom Suite
Fort Garry
9.6 out of 10, Exceptional, (20 reviews)
"Our overall stay was so smooth, owner provided a clean, tidy, well lit place to stay and responsive to our queries. Well recommended!"
Canada
Charmie Therese
The price is CA $82
CA $182 total
includes taxes & fees
Nov 16 - Nov 17
Welcoming Private 2 Bedroom Suite

8. St B. Living

St B. Living
Central St. Boniface
9.8 out of 10, Exceptional, (37 reviews)
"The space was perfect and was in walking distance to the hospital that the conference was. No complaints at all"
Canada
Carey
The price is CA $145
CA $192 total
includes taxes & fees
Nov 18 - Nov 19
St B. Living

9. Serenity meets class: Entire Basement Suite in Winnipeg

Serenity meets class: Entire Basement Suite in Winnipeg
St. Vital
9.4 out of 10, Exceptional, (36 reviews)
"It was quiet, private, clean and access to a washer and dryer was a definite plus. Amy questions we had were answered in a timely and throughout manner."
Canada
Carla
The price is CA $70
CA $156 total
includes taxes & fees
Nov 14 - Nov 15
Serenity meets class: Entire Basement Suite in Winnipeg

10. The Snug Spot,Retreat offers a warm and inviting escape for travelers.

The Snug Spot,Retreat offers a warm and inviting escape for travelers.
St. Vital
9.4 out of 10, Exceptional, (13 reviews)
"I enjoyed my stay, super comfy bed!!"
United States
Kim S.
The price is CA $89
CA $133 total
includes taxes & fees
Nov 16 - Nov 17
The Snug Spot,Retreat offers a warm and inviting escape for travelers.

11. 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 CA $81
CA $169 total
includes taxes & fees
Nov 20 - Nov 21
Peaceful and spacious one bed and rec-room for short or long stay

12. 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 CA $100
CA $221 total
includes taxes & fees
Nov 13 - Nov 14
Mary's Luxury Suite

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

Stormwater Haven: Peaceful, Stylish and comfortable space in South Winnipeg.
Fort Garry
8.6 out of 10, Excellent, (9 reviews)
"Newly renovated, convenient location"
Canada
paula
The price is CA $68
CA $147 total
includes taxes & fees
Nov 13 - Nov 14
Stormwater Haven: Peaceful, Stylish and comfortable space in South Winnipeg.

14. 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 CA $90
CA $162 total
includes taxes & fees
Nov 13 - Nov 14
Private Cozy 1 Bedroom Basement Suite

15. Wolseley Charmer- Main unit

Wolseley Charmer- Main unit
Winnipeg
10.0 out of 10, Exceptional, (3 reviews)
"It was a very nice place to stay."
Canada
Andrew
The price is CA $144
CA $261 total
includes taxes & fees
Nov 14 - Nov 15
Wolseley Charmer- Main unit

16. The Abode family space

The Abode family space
Fort Garry
The price is CA $120
CA $244 total
includes taxes & fees
Nov 19 - Nov 20
The Abode family space

17. 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 CA $113
CA $138 total
includes taxes & fees
Nov 15 - Nov 16
Separate Entrance Basement Suite

18. Cozy Nest - 1 Bedroom

Cozy Nest - 1 Bedroom
St. Vital
10.0 out of 10, Exceptional, (2 reviews)
"Very private, super new and super clean, convenient location and GREAT air conditioning."
Canada
Karryn
The price is CA $80
CA $174 total
includes taxes & fees
Nov 13 - Nov 14
Cozy Nest - 1 Bedroom

19. Haven in the Prairies 1BR S

Haven in the Prairies 1BR S
Fort Garry
The price is CA $70
CA $174 total
includes taxes & fees
Dec 7 - Dec 8
Haven in the Prairies 1BR S

20. Ruby's Place. Extremely neat and quiet place. Very close to basic malls and uofm

Ruby's Place. Extremely neat and quiet place. Very close to basic malls and uofm
Fort Garry
The price is CA $68
CA $132 total
includes taxes & fees
Nov 15 - Nov 16
Ruby's Place. Extremely neat and quiet place. Very close to basic malls and uofm
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

Headingley Vacation Homes information

Number of reviews
208
Accommodation
315 Vacation Homes
Lowest Price
CA $118
Highest Price
CA $1,115

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