Headingley Holiday Rentals

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Our top choices for Headingley holiday rentals

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 NZ$201
includes taxes & fees
4 Jan - 5 Jan 2026
Luxury: Home Away from Home with Private Entrance

Golden Eagle, Basement Suite

Golden Eagle, Basement Suite
Winnipeg
10.0 out of 10, Exceptional, (2)
"Place was very clean and kids enjoyed the ping-pong table and mini pool table. We felt a draft from the windows but they supplied a heater and extra blankets that helped. The tv was nice and big for the kids to game out with. Beds, bedding and pillows were very comfortable! I gave them 4 stars for accuracy of ad because at the top it says “entire house”, but throughout the ad it clarifies that it’s not, that we have the full basement. Which was good enough. But the kids were disappointed we...
Canada
Germaine B.
The price is NZ$190
includes taxes & fees
12 Jan - 13 Jan 2026
Golden Eagle, Basement Suite

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 NZ$228
includes taxes & fees
30 Dec - 31 Dec
Cozy Modern Suite - Peaceful Stay & Hwy Access

Charming lower level private entrance suite

Charming lower level private entrance suite
St. Vital
10.0 out of 10, Exceptional, (1)
The price is NZ$228
includes taxes & fees
31 Dec - 1 Jan 2026
Charming lower level private entrance suite

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 NZ$216
includes taxes & fees
3 Jan - 4 Jan 2026
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)
"This property was amazing would love to stay here again "
Canada
Oluwatimilehin
The price is NZ$231
includes taxes & fees
30 Dec - 31 Dec
Kelvista's suite

One-bedroom guest suite with private entry

One-bedroom guest suite with private entry
East Kildonan
10.0 out of 10, Exceptional, (6)
"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 NZ$157
includes taxes & fees
30 Dec - 31 Dec
One-bedroom guest suite with private entry

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 NZ$179
includes taxes & fees
3 Jan - 4 Jan 2026
Exquisite 1-bedroom basement in the quiet neighbourhood of Bonavista, Winnipeg

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 NZ$177
includes taxes & fees
4 Jan - 5 Jan 2026
2 Bed rooms|Private entrance|Free Parking|Self-Check-in into our Upscale Haven.

Elegant 1-Bedroom Basement Suite

Elegant 1-Bedroom Basement Suite
St. Vital
9.0 out of 10, Wonderful, (2)
"Had such a great stay. This was the first time I’ve ever used a service like this. The space was nice and clean. The bed was super comfortable. The host checked in on me and my stay multiple times and even help me with a few things. I highly recommended this stay. If I ever come to visit Winnipeg again, I would book this stay again. "
Canada
Braden K.
The price is NZ$186
includes taxes & fees
30 Dec - 31 Dec
Elegant 1-Bedroom Basement 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 NZ$223
includes taxes & fees
4 Jan - 5 Jan 2026
Welcoming Private 2 Bedroom Suite

Serenity meets class: Entire Basement Suite in Winnipeg

Serenity meets class: Entire Basement Suite in Winnipeg
St. Vital
8.8 out of 10, Excellent, (10)
"Accommodations were very nice. Extremely clean and well maintained. You could hear the people upstairs. Would have liked to have a table and chairs to eat at. Would stay again. "
United States
lisa a.
The price is NZ$162
includes taxes & fees
1 Jan - 2 Jan 2026
Serenity meets class: Entire Basement Suite in Winnipeg

Prairie Luxury 1 Bedrooms Home

Prairie Luxury 1 Bedrooms Home
Fort Garry
10.0 out of 10, Exceptional, (1)
The price is NZ$351
includes taxes & fees
1 Jan - 2 Jan 2026
Prairie Luxury 1 Bedrooms Home

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 NZ$215
includes taxes & fees
2 Jan - 3 Jan 2026
Afan Home of Joy

The perfect Retreat

The perfect Retreat
Peguis
8.4 out of 10, Very good, (5)
"Owner was very friendly and house was well maintained "
Canada
Erik
The price is NZ$157
includes taxes & fees
30 Dec - 31 Dec
The perfect Retreat

Charming Bedroom in Bonavista

Charming Bedroom in Bonavista
St. Vital
8.0 out of 10, Very good, (2)
"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 NZ$186
includes taxes & fees
8 Jan - 9 Jan 2026
Charming Bedroom in Bonavista

Winnipeg Radiant Home - A peaceful neighborhood with separate entrance

Winnipeg Radiant Home - A peaceful neighborhood with separate entrance
East Kildonan
9.0 out of 10, Wonderful, (6)
"It was clean, and everything we needed was included. Good location for our needs. The Host communicated with us promptly and politely but was not intrusive. "
Canada
Elisabeth
The price is NZ$158
includes taxes & fees
30 Dec - 31 Dec
Winnipeg Radiant Home - A peaceful neighborhood with separate entrance

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 NZ$174
includes taxes & fees
2 Jan - 3 Jan 2026
Cozy Haven 1-bedroom suite close to centre of Winnipeg

Morning glory cottage

Morning glory cottage
Peguis
8.6 out of 10, Excellent, (40)
"Good place "
United States
Roy H.
The price is NZ$149
includes taxes & fees
30 Dec - 31 Dec
Morning glory cottage

2 LUXURY BEDROOM IN BASEMENT FOR 4 PEOPLE !!!

2 LUXURY BEDROOM IN BASEMENT FOR 4 PEOPLE !!!
Fort Garry
9.4 out of 10, Exceptional, (8)
"It was a quick trip and a nice place to stay! Bridgwater area is very interesting to navigate, but all in all it was decent place to stay"
Canada
Vanessa M.
The price is NZ$196
includes taxes & fees
31 Dec - 1 Jan 2026
2 LUXURY BEDROOM IN BASEMENT FOR 4 PEOPLE !!!
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 favorite 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 depends 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 NZ$174 per night. Entering your travel dates in the search wizard you might find 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?

Cozy Haven 1-bedroom suite close to centre of Winnipeg: This holiday home rental outside of Headingley has air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

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.