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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 227 Vacation Homes in Headingley with updated reviews, rates, and availability.

Cheerful Tuxedo House with Hot Tub
Smart TV, fireplace

Cheerful Tuxedo House with Hot Tub

10.0 out of 10, Exceptional, (3)
"I love the location, very central! This was our second time staying here and would stay again!"
The price is AED 1,063
AED 2,320 total
includes taxes & fees
26 May - 27 May
Cheerful Tuxedo House with Hot Tub
1800 sq. 3 bed 2.5 bath New Home (2021)
Exterior detail

1800 sq. 3 bed 2.5 bath New Home (2021)

9.4 out of 10, Exceptional, (13)
"Nice house, everything you need to have a comfortable stay."
The price is AED 624
AED 840 total
includes taxes & fees
11 May - 12 May
1800 sq. 3 bed 2.5 bath New Home (2021)
Luxurious House in a Desired Location, King Bed
Pool

Luxurious House in a Desired Location, King Bed

10.0 out of 10, Exceptional, (29)
"Clean, bright, nicely decorated. I always enjoy staying here. "
The price is AED 651
AED 1,488 total
includes taxes & fees
12 May - 13 May
Luxurious House in a Desired Location, King Bed
Morning glory cottage
1 bedroom, iron/ironing board, free WiFi, bed sheets

Morning glory cottage

8.8 out of 10, Excellent, (33)
"Very friendly host great location"
The price is AED 159
AED 319 total
includes taxes & fees
7 May - 8 May
Morning glory cottage
3 floors character house
Fridge, microwave, oven, stovetop

3 floors character house

9.4 out of 10, Exceptional, (60)
"Property was clean and owner worked hard to accommodate us. Would recommend this place."
3 floors character house
Modern house in trendy location in South Winnipeg-Bridgwater Area
Pool

Modern house in trendy location in South Winnipeg-Bridgwater Area

10.0 out of 10, Exceptional, (23)
"We did a quick trip to Winnipeg to check out the Therma Spa. The location and accommodations were perfect! "
Modern house in trendy location in South Winnipeg-Bridgwater Area
King Bed Astounding Cinematic Sunset in trendy location, South City
Pool

King Bed Astounding Cinematic Sunset in trendy location, South City

10.0 out of 10, Exceptional, (39)
"Great stay. "
The price is AED 659
AED 1,497 total
includes taxes & fees
2 Jun - 3 Jun
King Bed Astounding Cinematic Sunset in trendy location, South City
House in Winnipeg's Prime Neighbourhood
Exterior

House in Winnipeg's Prime Neighbourhood

8.0 out of 10, Very Good, (1)
"Good value for money. Could use some better kitchen stuff and more consumables."
The price is AED 997
AED 1,304 total
includes taxes & fees
7 May - 8 May
House in Winnipeg's Prime Neighbourhood
Luxurious and Comfortable 3-Bedroom Bungalow Style House
Smart TV, fireplace

Luxurious and Comfortable 3-Bedroom Bungalow Style House

8.8 out of 10, Excellent, (19)
"Everything was as it was mentioned. Family was here to attend a wedding so o ly used it to "
Luxurious and Comfortable 3-Bedroom Bungalow Style House
Welcoming Private 2 Bedroom Suite
2 bedrooms, desk, iron/ironing board, free WiFi

Welcoming Private 2 Bedroom Suite

10.0 out of 10, Exceptional, (3)
"Fantastic property, excellent hosts! The beds were super comfy, everything we needed was accessible, and the place is in a fantastic location. Would definitely stay again, and highly recommend!"
The price is AED 186
AED 461 total
includes taxes & fees
19 May - 20 May
Welcoming Private 2 Bedroom Suite
Cozy 1BR Suite at Winnipeg South
Fridge, microwave, stovetop, dishwasher

Cozy 1BR Suite at Winnipeg South

10.0 out of 10, Exceptional, (2)
"The property was very nice and clean. We enjoyed our stay."
Cozy 1BR Suite at Winnipeg South
Bonavista LightHouse Deluxe Max
Property grounds

Bonavista LightHouse Deluxe Max

10.0 out of 10, Exceptional, (2)
"100% will definitely book this place in the future"
Bonavista LightHouse Deluxe Max
Full house Close to Down town and St Boniface
Exterior

Full house Close to Down town and St Boniface

Full house Close to Down town and St Boniface
2 beds/3 br with office very specious unit in StB with free parking and wifi.
Fridge, microwave, oven, stovetop

2 beds/3 br with office very specious unit in StB with free parking and wifi.

9.6 out of 10, Exceptional, (4)
"Perfect location for my need. Accessable and practical place"
2 beds/3 br with office very specious unit in StB with free parking and wifi.
Corydon Haven: Spacious Urban Retreat
Fridge, microwave, oven, stovetop

Corydon Haven: Spacious Urban Retreat

Corydon Haven: Spacious Urban Retreat
*1min Riverview Health 7min Downtown Free Parking
Point of interest

*1min Riverview Health 7min Downtown Free Parking

The price is AED 302
AED 710 total
includes taxes & fees
7 May - 8 May
*1min Riverview Health 7min Downtown Free Parking
St B. Living
Fridge, microwave, oven, stovetop

St B. Living

10.0 out of 10, Exceptional, (9)
"I enjoyed the house , I felt safe and it was very clean . The only problem we had was the parking, only parking for one small vehicle, other than that was the perfect place ."
The price is AED 375
AED 527 total
includes taxes & fees
11 May - 12 May
St B. Living
Cozy 2-Bedroom basement Suite with Private entrance South Winnipeg.
Fridge, microwave, stovetop, electric kettle

Cozy 2-Bedroom basement Suite with Private entrance South Winnipeg.

10.0 out of 10, Exceptional, (2)
"Had a great stay, pictures are accurate. Host was friendly and checked in with us. Would definitely stay here again. "
Cozy 2-Bedroom basement Suite with Private entrance South Winnipeg.
Luxury Home! A family-friendly home with 4 bedrooms and 3 bathrooms.
Fridge, microwave, oven, stovetop

Luxury Home! A family-friendly home with 4 bedrooms and 3 bathrooms.

9.6 out of 10, Exceptional, (4)
"I had a pleasant stay, it’s a beautiful house and the host was very helpful"
Luxury Home! A family-friendly home with 4 bedrooms and 3 bathrooms.
Afan Home of Joy
Property grounds

Afan Home of Joy

9.8 out of 10, Exceptional, (10)
"We enjoyed our 4-day stay, it was very clean, in a new home, quiet and spacious, and our hosts were very accomodating."
The price is AED 234
AED 486 total
includes taxes & fees
19 May - 20 May
Afan Home of Joy
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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Other property types in Headingley

Cheerful Tuxedo House with Hot Tub
Smart TV, fireplace

Cheerful Tuxedo House with Hot Tub

10.0 out of 10, Exceptional, (3)
"I love the location, very central! This was our second time staying here and would stay again!"
The price is AED 1,063
AED 2,320 total
includes taxes & fees
26 May - 27 May
Cheerful Tuxedo House with Hot Tub
Gorgeous 2 bed surreal view downtown laundry wifi
Fridge, microwave, stovetop, dishwasher

Gorgeous 2 bed surreal view downtown laundry wifi

8.4 out of 10, Very Good, (22)
"This is our second time staying in the property owned by this group, and we highly recommend. This is clean and quiet property. The location is amazing for going to Canada Life Centre and has great parking. We would definitely stay here again."
Gorgeous 2 bed surreal view downtown laundry wifi
House in Winnipeg's Prime Neighbourhood
Exterior

House in Winnipeg's Prime Neighbourhood

8.0 out of 10, Very Good, (1)
"Good value for money. Could use some better kitchen stuff and more consumables."
The price is AED 997
AED 1,304 total
includes taxes & fees
7 May - 8 May
House in Winnipeg's Prime Neighbourhood
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.