Headingley Holiday Rentals

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Our top choices for Headingley holiday rentals

Golden Eagle, Basement Suite

Golden Eagle, Basement Suite
Winnipeg
10.0 out of 10, Exceptional, (3 reviews)
"The host was really.nice and respectful, he is on top for respond to my needs concerning any supplies for my stay,, I just only want he be lenient a little with the guess for small details ( s.all hair in the bathroom/ carpet/ bed) after that I give 5 stars, and highly recommended. "
United States
Lesly
The price is AU$167
includes taxes & fees
19 Jan - 20 Jan
Golden Eagle, Basement Suite

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 AU$237
includes taxes & fees
23 Jan - 24 Jan
Amazing 2 bedroom basement with separate entrance

One-bedroom guest suite with private entry

One-bedroom guest suite with private entry
East Kildonan
10.0 out of 10, Exceptional, (6 reviews)
"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$122
includes taxes & fees
23 Jan - 24 Jan
One-bedroom guest suite with private entry

Blissful Home

Blissful Home
2.0 star property
Peguis
The price is AU$169
includes taxes & fees
22 Jan - 23 Jan
Blissful Home

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 reviews)
"Nice and attractive place … host has good communication "
United States
Benson-Ifere E.
The price is AU$202
includes taxes & fees
9 Feb - 10 Feb
Cozy 2-Bedroom Home in St-Boniface – 5 Min Walk to Food, Fuel & More

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 AU$196
includes taxes & fees
20 Jan - 21 Jan
Kelvista's suite

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 AU$219
includes taxes & fees
21 Jan - 22 Jan
AVOCADO EXECUTIVE SUITES

Modern, Prime Location & Comfort

Modern, Prime Location & Comfort
Ebby-Wentworth
10.0 out of 10, Exceptional, (2 reviews)
"We stayed here because we were in town for an event at the Pan Am pool. It is a beautiful place with all immunities we needed. Beds were very comfortable and the place was spotless. It’s clear that it’s been through a total renovation very recently. Parking was easy and a relatively short walk (10 minutes at our pace) to grocery, Canadian Tire and a few restaurants. Also easy to get to other parts of town like the airport and Fork district, both within about 15 minutes. Only one recommendation,...
Canada
Simon H.
The price is AU$257
includes taxes & fees
1 Feb - 2 Feb
Modern, Prime Location & Comfort

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$548
includes taxes & fees
1 Feb - 2 Feb
Riverfront City Escape w/Hot Tub, 2 King, Gym, Sleeps 12, Firepit, Kayaks

Welcoming Private 2 Bedroom Suite

Welcoming Private 2 Bedroom Suite
Fort Garry
9.2 out of 10, Wonderful, (11 reviews)
"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$196
includes taxes & fees
24 Jan - 25 Jan
Welcoming Private 2 Bedroom Suite

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 reviews)
"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$158
includes taxes & fees
20 Jan - 21 Jan
Exquisite 1-bedroom basement in the quiet neighbourhood of Bonavista, Winnipeg

Cozy Basement Suite in Winnipeg

Cozy Basement Suite in Winnipeg
2.0 star property
Transcona
The price is AU$177
includes taxes & fees
19 Jan - 20 Jan
Cozy Basement Suite in Winnipeg

*1min Riverview Health 7min Downtown Free Parking

*1min Riverview Health 7min Downtown Free Parking
Winnipeg
9.0 out of 10, Wonderful, (8 reviews)
"The home was as advertised. The beds were really good. The kitchen should be better stocked for a home. The carpet in the living room should be replaced. We enjoyed our stay."
Canada
adina w.
The price is AU$302
includes taxes & fees
29 Jan - 30 Jan
*1min Riverview Health 7min Downtown Free Parking

Stylish & Spacious | Minutes from Downtown

Stylish & Spacious | Minutes from Downtown
Central St. Boniface
10.0 out of 10, Exceptional, (4 reviews)
"Well stocked, spacious, and central. Glad I stayed here. "
Canada
Dale K.
The price is AU$270
includes taxes & fees
26 Jan - 27 Jan
Stylish & Spacious | Minutes from Downtown

*Shop & Dine | Free Parking | 7 min to Airport*

*Shop & Dine | Free Parking | 7 min to Airport*
King Edward
10.0 out of 10, Exceptional, (2 reviews)
"Newer development, clean, beautifully designed. Comforts of home. Host replies in a timely matter. Enjoyed my stay with no hassle. "
Canada
Lori
The price is AU$264
includes taxes & fees
26 Jan - 27 Jan
*Shop & Dine | Free Parking | 7 min to Airport*

Affordable Bachelor Near HSC & Downtown

Affordable Bachelor Near HSC & Downtown
2.0 star property
West Alexander
The price is AU$210
includes taxes & fees
21 Jan - 22 Jan
Affordable Bachelor Near HSC & Downtown

*Cozy & Spacious | Free Parking | 15 min Downtown*

*Cozy & Spacious | Free Parking | 15 min Downtown*
St. Vital
8.0 out of 10, Very good, (4 reviews)
"Property was clean and well suited for our trip. Karl even checked in a couple times to see if we needed anything. "
United States
cynthia h.
The price is AU$296
includes taxes & fees
19 Jan - 20 Jan
*Cozy & Spacious | Free Parking | 15 min Downtown*

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 review)
"Very nice quiet place to stay."
Canada
Lisa W.
The price is AU$151
includes taxes & fees
31 Jan - 1 Feb
Duniques unique home Fully furnished 2 bedroom basement suite

Charming Bedroom in Bonavista

Charming Bedroom in Bonavista
St. Vital
8.0 out of 10, Very good, (2 reviews)
"The place was very clean and very very new. There was still the stickers from original packaging on the TV and some appliances. Apparently the laundry room is locked and you are only given access if you stay 4 nights. This was not made clear when booking. I was also under the impression that I was renting the whole house and that the second bedroom could be rented if I chose so. However, j found out that there would be a person I didn't know who rented out the slate bedroom. Luckily, the owner...
United States
Wesley R.
The price is AU$164
includes taxes & fees
19 Jan - 20 Jan
Charming Bedroom in Bonavista

Spacious new 3 Bedroom, sleeps 10, King Bed, 8min to YWG

Spacious new 3 Bedroom, sleeps 10, King Bed, 8min to YWG
2.0 star property
Deer Lodge
The price is AU$292
includes taxes & fees
22 Jan - 23 Jan
Spacious new 3 Bedroom, sleeps 10, King Bed, 8min to YWG
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

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$167 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?

Luxurious House in a Desired Location, King Bed: This holiday home rental outside of Headingley offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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, Beaudry Provincial Park and John Blumberg Golf Course 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.