Search Vacation Homes in Headingley

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Compare 232 Vacation Homes in Headingley with updated reviews, rates, and availability.

Luxurious House in a Desired Location, King Bed
Pool

Luxurious House in a Desired Location, King Bed

10.0 out of 10, Exceptional, (31)
"Clean, bright, nicely decorated. I always enjoy staying here. "
Luxurious House in a Desired Location, King Bed
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, (41)
"Great stay. "
The price is AED 719
AED 1,578 total
includes taxes & fees
28 Jun - 29 Jun
King Bed Astounding Cinematic Sunset in trendy location, South City
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.
Serenity meets class: Entire Basement Suite in Winnipeg
Interior

Serenity meets class: Entire Basement Suite in Winnipeg

10.0 out of 10, Exceptional, (1)
"Hosts were very friendly and accommodating and take good care of their property."
Serenity meets class: Entire Basement Suite in Winnipeg
Spacious House in Winnipeg
Living area

Spacious House in Winnipeg

4.0 out of 10, (1)
"We have been using VRBO for many years and have always had a great experience with nice properties and wonderful hosts. Our 5 night stay at the Spacious House in Winnipeg was disappointing on many levels. The listing did not state that there was a rental suite in the basement. We had to contact the host to find out how to check in as we were not sent any info through VRBO. There was no binder of information in the unit to explain anything (eg. Recycling, garbage, laundry, etc.). The basement...
Spacious House in Winnipeg
House with great location
Terrace/patio

House with great location

6.0 out of 10, (3)
"Great place. Will be booking again "
House with great location
Cheerful Tuxedo House with Hot Tub
Smart TV, fireplace

Cheerful Tuxedo House with Hot Tub

10.0 out of 10, Exceptional, (9)
The price is AED 1,203
AED 2,495 total
includes taxes & fees
3 Jul - 4 Jul
Cheerful Tuxedo House with Hot Tub
New 2 bedroom basement suite
2 bedrooms, desk, free WiFi, bed sheets

New 2 bedroom basement suite

10.0 out of 10, Exceptional, (11)
"Very nice place to stay and very congenial host."
New 2 bedroom basement suite
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 1,203
AED 1,591 total
includes taxes & fees
25 Jun - 26 Jun
House in Winnipeg's Prime Neighbourhood
St B. Living
Fridge, microwave, oven, stovetop

St B. Living

10.0 out of 10, Exceptional, (10)
"Very clean rental. Easy to access and property owner was very responsive. "
The price is AED 377
AED 527 total
includes taxes & fees
3 Jun - 4 Jun
St B. Living
Restful 4 bedroom TownHome
Fridge, microwave, stovetop, coffee/tea maker

Restful 4 bedroom TownHome

8.8 out of 10, Excellent, (8)
"The place was perfect for our quick trip to Winnipeg. Check in and cleanliness was great, wonderful communication throughout our stay. Would definitely stay again."
Restful 4 bedroom TownHome
Cozy 1BR Suite at Winnipeg South
Fridge, microwave, stovetop, dishwasher

Cozy 1BR Suite at Winnipeg South

8.6 out of 10, Excellent, (4)
"The property was very nice and clean. We enjoyed our stay."
Cozy 1BR Suite at Winnipeg South
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, (24)
"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
River Heights+Striking 4 Bdr Home+Parking(759)
Smart TV, Netflix, streaming services

River Heights+Striking 4 Bdr Home+Parking(759)

9.0 out of 10, Wonderful, (4)
"Nice place"
River Heights+Striking 4 Bdr Home+Parking(759)
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!"
Welcoming Private 2 Bedroom Suite
Cozy Home away from Home in a Basement with a separate entrance
Fridge, microwave, stovetop, coffee/tea maker

Cozy Home away from Home in a Basement with a separate entrance

10.0 out of 10, Exceptional, (1)
"My wife and I stayed in Winnipeg for a few nights in Dec 2022. The suite was easily accessible, located in the lower level of a house in a residential neighborhood. Was refreshing to get away from 'corporate' for a bit. Bed was comfortable and everything that we needed was provided - even creamers for the coffee. We didn't use the TV, but apparently it has several thousand channels so you can surf to your heart's content. The host, Christiana, was very attentive and made sure we had all that we...
The price is AED 214
AED 365 total
includes taxes & fees
5 Jun - 6 Jun
Cozy Home away from Home in a Basement with a separate entrance
The Wooden Nest | Your Comfy Relaxing Escape
Pool

The Wooden Nest | Your Comfy Relaxing Escape

The price is AED 375
AED 813 total
includes taxes & fees
8 Jun - 9 Jun
The Wooden Nest | Your Comfy Relaxing Escape
1800 sq. 3 bed 2.5 bath New Home (2021)
Exterior detail

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

9.6 out of 10, Exceptional, (17)
"It is a nice place with a lot of rooms for a large group of people. We were 8 adults and all enjoyed the stay. "
The price is AED 535
AED 719 total
includes taxes & fees
18 Jun - 19 Jun
1800 sq. 3 bed 2.5 bath New Home (2021)
Spacious Basement Suite in Bonavista With Separate Entrance
TV

Spacious Basement Suite in Bonavista With Separate Entrance

9.6 out of 10, Exceptional, (8)
"The experience was really good. The place was so clean peaceful and lovely."
Spacious Basement Suite in Bonavista With Separate Entrance
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
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free