Headingley Vacation Rentals

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Check prices for these dates

In two weeks
May 1 - May 3
In two months
Jun 12 - Jun 14
In three months
Jul 10 - Jul 12
In four months
Aug 7 - Aug 9

Our top choices for Headingley vacation rentals

Interior

Suite with facilities to make you feel at home

Suite with facilities to make you feel at home
Windsor Park
The price is ￥1,393,752
￥1,810,071 total
includes taxes & fees
Apr 18 - Apr 19
Suite with facilities to make you feel at home
Smart TV, fireplace

Magnificent Stylish Escape

Magnificent Stylish Escape
Fort Garry
The price is ￥73,067
￥191,515 total
includes taxes & fees
Apr 30 - May 1
Magnificent Stylish Escape
Private kitchen

Nice 2 bed basement + private entrance

Nice 2 bed basement + private entrance
Peguis
The price is ￥522,657
￥705,695 total
includes taxes & fees
Apr 18 - Apr 19
Nice 2 bed basement + private entrance
Interior

Cheerful Tuxedo House with Hot Tub

Cheerful Tuxedo House with Hot Tub
Tuxedo
9.8 out of 10, Exceptional, (40 reviews)
"We totally enjoyed our stay!"
Canada
peter S.
The price is ￥47,884
￥116,843 total
includes taxes & fees
Apr 29 - Apr 30
Cheerful Tuxedo House with Hot Tub
Exterior detail

Cozy Basement Suite in Winnipeg

Cozy Basement Suite in Winnipeg
St. Vital
8.0 out of 10, Very Good, (2 reviews)
"Great host, great amenities "
United States
Alyce M.
The price is ￥10,410
￥19,917 total
includes taxes & fees
Apr 19 - Apr 20
Cozy Basement Suite in Winnipeg
Interior

Modern 5 bedroom Lake view home in Prairie Pointe, winnipeg

Modern 5 bedroom Lake view home in Prairie Pointe, winnipeg
Fort Garry
10.0 out of 10, Exceptional, (1 review)
"The place was spotless and the host was absolutely very courteous. "
Canada
Lilly
Modern 5 bedroom Lake view home in Prairie Pointe, winnipeg
Smart TV, fireplace

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 ￥13,066
￥18,971 total
includes taxes & fees
Apr 19 - Apr 20
Separate Entrance Basement Suite
Pool

King Bed Astounding Cinematic Sunset in trendy location, South City

King Bed Astounding Cinematic Sunset in trendy location, South City
Fort Garry
10.0 out of 10, Exceptional, (54 reviews)
"Absolutely gorgeous place. Quiet, relaxing. A dream stay. "
Canada
Jeremy
King Bed Astounding Cinematic Sunset in trendy location, South City
Exterior

Amazing 2 bedroom basement with separate entrance

Amazing 2 bedroom basement with separate entrance
St. Vital
10.0 out of 10, Exceptional, (1 review)
"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
Sharon W.
The price is ￥20,906
￥29,618 total
includes taxes & fees
Apr 30 - May 1
Amazing 2 bedroom basement with separate entrance
Room

Sally Room 101-Place in Devonshire Park

Sally Room 101-Place in Devonshire Park
Peguis
The price is ￥6,246
￥19,096 total
includes taxes & fees
Apr 25 - Apr 26
Sally Room 101-Place in Devonshire Park
Interior

🌎Modern 3 bedroom home w/street park’n close to ✈️

🌎Modern 3 bedroom home w/street park’n close to ✈️
Weston
10.0 out of 10, Exceptional, (3 reviews)
"This property is beautiful. The owner is top hostess she went above and beyond for us. Will definitely being staying here again"
Canada
Aldeana L.
The price is ￥18,003
￥84,193 total
includes taxes & fees
Apr 30 - May 1
🌎Modern 3 bedroom home w/street park’n close to ✈️
Interior

Restful Haven

Restful Haven
Fort Garry
The price is ￥10,410
￥19,917 total
includes taxes & fees
Apr 23 - Apr 24
Restful Haven
Exterior detail

Kelvista's suite

Kelvista's suite
St. Vital
9.6 out of 10, Exceptional, (11 reviews)
"This property was amazing would love to stay here again "
Canada
Oluwatimilehin
The price is ￥8,096
￥21,970 total
includes taxes & fees
Apr 24 - Apr 25
Kelvista's suite
Exterior

Prairie Luxury 2 Bedrooms Home

Prairie Luxury 2 Bedrooms Home
Fort Garry
9.4 out of 10, Exceptional, (6 reviews)
"Great place. Easy, convenient location. Clean and spacious."
Canada
Randy H.
The price is ￥9,779
￥31,485 total
includes taxes & fees
Apr 19 - Apr 20
Prairie Luxury 2 Bedrooms Home
Interior

The Abode family space

The Abode family space
Fort Garry
The price is ￥13,938
￥31,253 total
includes taxes & fees
Apr 30 - May 1
The Abode family space
Interior

AVOCADO EXECUTIVE SUITES

AVOCADO EXECUTIVE SUITES
St. Vital
8.0 out of 10, Very Good, (3 reviews)
"The apartment was very neat, I got immediate response when I had issues. I will always recommend for family and friends. "
Canada
TITILAYO O.
The price is ￥9,369
￥21,422 total
includes taxes & fees
Apr 23 - Apr 24
AVOCADO EXECUTIVE SUITES
Private kitchen

Cozy two-bedroom retreat in the heart of St. Boniface,

Cozy two-bedroom retreat in the heart of St. Boniface,
Central St. Boniface
The price is ￥10,453
￥27,433 total
includes taxes & fees
Apr 30 - May 1
Cozy two-bedroom retreat in the heart of St. Boniface,
Interior

St. Thérèse’s Nest: Your Peaceful Retreat Minutes from the Pulse of the City

St. Thérèse’s Nest: Your Peaceful Retreat Minutes from the Pulse of the City
Lord Roberts
10.0 out of 10, Exceptional, (1 review)
"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
Joanne S.
The price is ￥18,737
￥49,370 total
includes taxes & fees
Apr 22 - Apr 23
St. Thérèse’s Nest: Your Peaceful Retreat Minutes from the Pulse of the City
Exterior

Amazing 2-Bedroom Basement Suite

Amazing 2-Bedroom Basement Suite
St. Vital
The price is ￥13,275
￥26,087 total
includes taxes & fees
Apr 30 - May 1
Amazing 2-Bedroom Basement Suite
Living area

Velvet&Rose|Elegant Private 2BR Suite|Free Parking|Wi-Fi

Velvet&Rose|Elegant Private 2BR Suite|Free Parking|Wi-Fi
Transcona
The price is ￥8,015
￥15,032 total
includes taxes & fees
Apr 21 - Apr 22
Velvet&Rose|Elegant Private 2BR Suite|Free Parking|Wi-Fi
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

Victoria Inn Hotel and Convention Centre Winnipeg

Victoria Inn Hotel and Convention Centre Winnipeg

6/10 Okay
"Our ceiling had strips of dust hanging from stucco in room, peeling wallpaper. Great pool for the littles. Didn’t utilize the restaurant during our stay "
Liz 1-night trip
Posted 2 hours ago
Victoria Inn Hotel and Convention Centre Winnipeg

Find out more about Headingley

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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?

*New & Modern Home | Free Parking | 5 mins Downtown*: This vacation home rental outside of Headingley is equipped with a selection of books, 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 Beaudry Provincial Park 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.