Headingley Holiday Rentals

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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Holiday Rentals in Headingley

Exterior
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 AU$177
includes taxes & fees
17 Dec - 18 Dec
Golden Eagle, Basement Suite
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

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 AU$438
includes taxes & fees
13 Dec - 14 Dec
St. Thérèse’s Nest: Your Peaceful Retreat Minutes from the Pulse of the City
Private kitchen
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 AU$291
includes taxes & fees
7 Dec - 8 Dec
Stylish & Spacious | Minutes from Downtown
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

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 AU$215
includes taxes & fees
10 Dec - 11 Dec
Cozy 2-Bedroom Home in St-Boniface – 5 Min Walk to Food, Fuel & More
Private kitchen
Cozy 3-Bedroom Basement Suite with Private Entrance

Cozy 3-Bedroom Basement Suite with Private Entrance

2.0 star property
Transcona
The price is AU$282
includes taxes & fees
14 Dec - 15 Dec
Cozy 3-Bedroom Basement Suite with Private Entrance
Fridge, microwave, stovetop, coffee/tea maker
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 AU$222
includes taxes & fees
13 Dec - 14 Dec
AVOCADO EXECUTIVE SUITES
Smart TV, computer monitors
One-bedroom guest suite with private entry

One-bedroom guest suite with private entry

East Kildonan
10.0 out of 10, Exceptional, (5)
"Cute, clean basement suite in a quiet neighborhood. Little out of the way of amenities but easily accessible if one has a vehicle. Will stay again if ever in town and in the area"
United States
Devo A.
The price is AU$134
includes taxes & fees
4 Dec - 5 Dec
One-bedroom guest suite with private entry
Property grounds
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 AU$205
includes taxes & fees
8 Dec - 9 Dec
Welcoming Private 2 Bedroom Suite
Living area
Peaceful Tyson Trail Retreat .

Peaceful Tyson Trail Retreat .

2.0 star property
Transcona
The price is AU$179
includes taxes & fees
5 Dec - 6 Dec
Peaceful Tyson Trail Retreat .
Fridge, microwave, coffee/tea maker, electric kettle
Duniques unique home Fully furnished 2 bedroom basement suite

Duniques unique home Fully furnished 2 bedroom basement suite

Fort Garry
8.0 out of 10, Very good, (1)
"Very nice quiet place to stay."
Canada
Lisa W.
The price is AU$156
includes taxes & fees
14 Dec - 15 Dec
Duniques unique home Fully furnished 2 bedroom basement suite
Microwave, stovetop
Exquisite 1-bedroom basement in the quiet neighbourhood of Bonavista, Winnipeg

Exquisite 1-bedroom basement in the quiet neighbourhood of Bonavista, Winnipeg

St. Vital
10.0 out of 10, Exceptional, (2)
"Overall enjoyed my stay the place was well kept and completely hosted myself and two friends for the weekend. In a great neighborhood felt safe and a beautiful park walking distance away. I recommend it’s comfortable and affordable."
Canada
Hana S.
The price is AU$154
includes taxes & fees
4 Dec - 5 Dec
Exquisite 1-bedroom basement in the quiet neighbourhood of Bonavista, Winnipeg
Interior
Cozy Haven 1-bedroom suite close to centre of Winnipeg

Cozy Haven 1-bedroom suite close to centre of Winnipeg

Winnipeg
10.0 out of 10, Exceptional, (2)
"Would definitely stay here again if I’m ever in Winnipeg! "
Canada
Ashton P.
The price is AU$155
includes taxes & fees
8 Dec - 9 Dec
Cozy Haven 1-bedroom suite close to centre of Winnipeg
Fridge, microwave, stovetop, coffee/tea maker
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 AU$240
includes taxes & fees
14 Dec - 15 Dec
Amazing 2 bedroom basement with separate entrance
1 bedroom, iron/ironing board, free WiFi, bed sheets
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 AU$196
includes taxes & fees
14 Dec - 15 Dec
Cozy Modern Suite - Peaceful Stay & Hwy Access
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.

Transcona
9.6 out of 10, Exceptional, (10)
"Good location to stay"
United States
Sarah
The price is AU$186
includes taxes & fees
6 Dec - 7 Dec
2 Bed rooms|Private entrance|Free Parking|Self-Check-in into our Upscale Haven.
Terrace/patio
Riverfront City Escape w/Hot Tub, 2 King, Gym, Sleeps 12, Firepit, Kayaks

Riverfront City Escape w/Hot Tub, 2 King, Gym, Sleeps 12, Firepit, Kayaks

2.0 star property
St. Vital
The price is AU$593
includes taxes & fees
7 Dec - 8 Dec
Riverfront City Escape w/Hot Tub, 2 King, Gym, Sleeps 12, Firepit, Kayaks
Property grounds
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 AU$282
includes taxes & fees
10 Dec - 11 Dec
Stormwater Haven: Peaceful, Stylish and comfortable space in South Winnipeg.
Exterior detail
Private Cozy 1 Bedroom Basement Suite

Private Cozy 1 Bedroom Basement Suite

Fort Garry
9.2 out of 10, Wonderful, (5)
"Amenities. Very bright and a floor lamp and small end table would be good. No where to cook a meal. Microwave doesn’t cut the mustard! Wide open to upstairs. Concept is good, but these things would be great. We did like it. "
Canada
Ray
The price is AU$192
includes taxes & fees
14 Dec - 15 Dec
Private Cozy 1 Bedroom Basement Suite
Interior
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 AU$179
includes taxes & fees
8 Dec - 9 Dec
Luxury: Home Away from Home with Private Entrance
Exterior detail
Fully Furnished Basement Unit – Private Entrance Included

Fully Furnished Basement Unit – Private Entrance Included

St. Vital
8.4 out of 10, Very good, (7)
"Well maintained and very clean."
Canada
Calvin G.
The price is AU$160
includes taxes & fees
8 Dec - 9 Dec
Fully Furnished Basement Unit – Private Entrance Included
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

10/10 Excellent
"Excellent "
Kathy 2-night trip
Posted 15 hours ago
Victoria Inn Hotel and Convention Centre Winnipeg

Find out more about Headingley

Everything you need to know about Headingley holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Headingley holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Headingley holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Headingley holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Headingley. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Headingley holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Headingley holiday rentals we have selected for you start as low as AU$134 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Headingley rentals

At Expedia, we put the best Headingley holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Headingley rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Headingley holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Headingley. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.