Headingley Holiday Rentals

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Check prices for these dates

In two weeks
2 Jan - 4 Jan
In two months
13 Feb - 15 Feb
In three months
13 Mar - 15 Mar
In four months
10 Apr - 12 Apr

Our top choices for Headingley holiday rentals

Fridge, microwave, stovetop, coffee/tea maker
Kelvista's suite

Kelvista's suite

Kelvista's suite
St. Vital
9.6 out of 10, Exceptional, (11)
"This property was amazing would love to stay here again "
Canada
Oluwatimilehin
The price is HK$367
HK$1,046 total
includes taxes & fees
20 Dec - 21 Dec
Kelvista's suite
Exterior
Golden Eagle, Basement Suite

Golden Eagle, Basement Suite

Golden Eagle, Basement Suite
Winnipeg
10.0 out of 10, Exceptional, (1)
"Very clean and as advertised. Beds were very comfortable."
Canada
Harold
The price is HK$407
HK$825 total
includes taxes & fees
21 Dec - 22 Dec
Golden Eagle, Basement Suite
1 bedroom, iron/ironing board, free WiFi, bed sheets
Cozy Modern Suite - Peaceful Stay & Hwy Access

Cozy Modern Suite - Peaceful Stay & Hwy Access

Cozy Modern Suite - Peaceful Stay & Hwy Access
Fort Garry
9.6 out of 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
Nadine M.
The price is HK$356
HK$1,032 total
includes taxes & fees
21 Dec - 22 Dec
Cozy Modern Suite - Peaceful Stay & Hwy Access
Property grounds
Welcoming Private 2 Bedroom Suite

Welcoming Private 2 Bedroom Suite

Welcoming Private 2 Bedroom Suite
Fort Garry
9.2 out of 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
Ellie
The price is HK$424
HK$1,012 total
includes taxes & fees
20 Dec - 21 Dec
Welcoming Private 2 Bedroom Suite
Interior
Luxury: Home Away from Home with Private Entrance

Luxury: Home Away from Home with Private Entrance

Luxury: Home Away from Home with Private Entrance
Transcona
8.6 out of 10, Excellent, (4)
"Nice suite, clean and relatively new. some defects pointed out to the owner and very receptive of comments."
Canada
Bill H.
The price is HK$282
HK$912 total
includes taxes & fees
20 Dec - 21 Dec
Luxury: Home Away from Home with Private Entrance
Smart TV
Cozy Basement Suite in Winnipeg

Cozy Basement Suite in Winnipeg

Cozy Basement Suite in Winnipeg
2.0 star property
Transcona
The price is HK$452
HK$912 total
includes taxes & fees
21 Dec - 22 Dec
Cozy Basement Suite in Winnipeg
Fridge, microwave, stovetop, coffee/tea maker
AVOCADO EXECUTIVE SUITES

AVOCADO EXECUTIVE SUITES

AVOCADO EXECUTIVE SUITES
St. Vital
8.0 out of 10, Very good, (3)
"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 HK$526
HK$1,133 total
includes taxes & fees
20 Dec - 21 Dec
AVOCADO EXECUTIVE SUITES
Property grounds
Stormwater Haven: Peaceful, Stylish and comfortable space in South Winnipeg.

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

Stormwater Haven: Peaceful, Stylish and comfortable space in South Winnipeg.
2.0 star property
Fort Garry
The price is HK$565
HK$1,447 total
includes taxes & fees
20 Dec - 21 Dec
Stormwater Haven: Peaceful, Stylish and comfortable space in South Winnipeg.
Exterior
Spacious Century Gem in Downtown Winnipeg with parking

Spacious Century Gem in Downtown Winnipeg with parking

Spacious Century Gem in Downtown Winnipeg with parking
2.0 star property
Winnipeg
The price is HK$407
HK$859 total
includes taxes & fees
23 Dec - 24 Dec
Spacious Century Gem in Downtown Winnipeg with parking
Interior
Serene 2-bedroom private basement suite house in beautiful Winnipeg

Serene 2-bedroom private basement suite house in beautiful Winnipeg

Serene 2-bedroom private basement suite house in beautiful Winnipeg
2.0 star property
Winnipeg
The price is HK$616
HK$905 total
includes taxes & fees
2 Jan - 3 Jan 2026
Serene 2-bedroom private basement suite house in beautiful Winnipeg
1 bedroom, iron/ironing board, free WiFi, bed sheets
Morning glory cottage

Morning glory cottage

Morning glory cottage
Peguis
8.6 out of 10, Excellent, (40)
"Good place "
United States
Roy H.
The price is HK$339
HK$678 total
includes taxes & fees
20 Dec - 21 Dec
Morning glory cottage
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

St. Thérèse’s Nest: Your Peaceful Retreat Minutes from the Pulse of the City
2.0 star property
Lord Roberts
10.0 out of 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
Joanne S.
The price is HK$813
HK$2,245 total
includes taxes & fees
20 Dec - 21 Dec
St. Thérèse’s Nest: Your Peaceful Retreat Minutes from the Pulse of the City
Exterior detail
Private Cozy 1 Bedroom Basement Suite

Private Cozy 1 Bedroom Basement Suite

Private Cozy 1 Bedroom Basement Suite
Fort Garry
9.2 out of 10, Wonderful, (5)
"Nice clean place to stay"
United States
Thomas B.
The price is HK$508
HK$979 total
includes taxes & fees
20 Dec - 21 Dec
Private Cozy 1 Bedroom Basement Suite
Exterior detail
Afan Home of Joy

Afan Home of Joy

Afan Home of Joy
Peguis
9.6 out of 10, Exceptional, (22)
"This is a wonderful space and we enjoyed our time staying here. Will would definitely stay again!"
Canada
Desiree R.
The price is HK$447
HK$973 total
includes taxes & fees
28 Dec - 29 Dec
Afan Home of Joy
Private kitchen
Avocado Executive Suite 1

Avocado Executive Suite 1

Avocado Executive Suite 1
St. Vital
8.0 out of 10, Very good, (1)
"Only thing there wasn’t an oven. Had a couple of issues but they were resolved quickly "
Canada
Craig B.
The price is HK$452
HK$1,312 total
includes taxes & fees
19 Jan - 20 Jan 2026
Avocado Executive Suite 1
Dining
2 Bed rooms|Private entrance|Free Parking|Self-Check-in into our Upscale Haven.

2 Bed rooms|Private entrance|Free Parking|Self-Check-in into our Upscale Haven.

2 Bed rooms|Private entrance|Free Parking|Self-Check-in into our Upscale Haven.
Transcona
9.6 out of 10, Exceptional, (10)
"Good location to stay"
United States
Sarah
The price is HK$423
HK$851 total
includes taxes & fees
18 Jan - 19 Jan 2026
2 Bed rooms|Private entrance|Free Parking|Self-Check-in into our Upscale Haven.
Private kitchen
Cozy 2-Bedroom Home in St-Boniface – 5 Min Walk to Food, Fuel & More

Cozy 2-Bedroom Home in St-Boniface – 5 Min Walk to Food, Fuel & More

Cozy 2-Bedroom Home in St-Boniface – 5 Min Walk to Food, Fuel & More
Central St. Boniface
10.0 out of 10, Exceptional, (3)
"Nice and attractive place … host has good communication "
United States
Benson-Ifere E.
The price is HK$508
HK$979 total
includes taxes & fees
20 Dec - 21 Dec
Cozy 2-Bedroom Home in St-Boniface – 5 Min Walk to Food, Fuel & More
Private kitchen
Stylish & Spacious | Minutes from Downtown

Stylish & Spacious | Minutes from Downtown

Stylish & Spacious | Minutes from Downtown
Central St. Boniface
10.0 out of 10, Exceptional, (3)
"Well stocked, spacious, and central. Glad I stayed here. "
Canada
Dale K.
The price is HK$674
HK$1,495 total
includes taxes & fees
22 Dec - 23 Dec
Stylish & Spacious | Minutes from Downtown
Fridge, microwave, stovetop, coffee/tea maker
Amazing 2 bedroom basement with separate entrance

Amazing 2 bedroom basement with separate entrance

Amazing 2 bedroom basement with separate entrance
St. Vital
10.0 out of 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
Sharon W.
The price is HK$875
HK$1,280 total
includes taxes & fees
26 Dec - 27 Dec
Amazing 2 bedroom basement with separate entrance
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

Travelodge by Wyndham Winnipeg East

Travelodge by Wyndham Winnipeg East

10/10 Excellent
"Room is great, backdoor opens into paradise courtyard with real tropical plants, a hot tub, sauna, and swimming pool! Pub had great service, good burgers & fries, and pints of Fort Garry Dark! "
Dave 1-night trip
Posted 3 days ago
Travelodge by Wyndham Winnipeg East

Find out more about Headingley

Search for holiday rentals in Headingley on Expedia! You can easily find your home rentals, villas, holiday apartments in Headingley using one of the methods below:

  • View our selection of featured holiday rentals in Headingley
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  • Enter your travel dates to view the best deals on holiday rentals in Headingley while they last

Look no further and take a look at our great range of rental properties in Headingley!

Frequently asked questions

Can I find a holiday rental in Headingley?

Yes, there are holiday rentals in Headingley close to Thunder Rapids Fun Park, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Headingley has a good selection of coffee shops. Make sure you have time to check out the hockey games and riverfront during your trip.

What are some of the best holiday rentals that Headingley has to offer?

Morning glory cottage: This holiday home rental outside of Headingley has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a microwave to make your meal-planning easier.

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 John Blumberg Softball Complex are other places worth a visit.

What are holiday rentals like in Headingley?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Headingley. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from public hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for families.