Headingley Holiday Rentals

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Holiday Rentals in Headingley

Kelvista's suite

10.0 out of 10, Exceptional, (4)
"The place was perfect. Thank you for making our stay in Winnipeg memorable. "
The price is NZ$211
includes taxes & fees
11 Aug - 12 Aug
Kelvista's suite

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

10.0 out of 10, Exceptional, (1)
"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."
The price is NZ$196
includes taxes & fees
24 July - 25 July
Exquisite 1-bedroom basement in the quiet neighbourhood of Bonavista, Winnipeg

One-bedroom guest suite with private entry

10.0 out of 10, Exceptional, (2)
"Easy to find, efficient check in and communication with host. The space was exactly as advertised. Would highly recommend."
The price is NZ$153
includes taxes & fees
28 July - 29 July
One-bedroom guest suite with private entry

Cozy Home away from Home in a Basement with a separate entrance

10.0 out of 10, Exceptional, (5)
"My wife and I stayed in Winnipeg for a few nights in Dec 2022. The suite was easily accessible, located in the lower level of a house in a residential neighborhood. Was refreshing to get away from 'corporate' for a bit. Bed was comfortable and everything that we needed was provided - even creamers for the coffee. We didn't use the TV, but apparently it has several thousand channels so you can surf to your heart's content. The host, Christiana, was very attentive and made sure we had all that we...
The price is NZ$187
includes taxes & fees
27 July - 28 July
Cozy Home away from Home in a Basement with a separate entrance

Zillion’s ville. Delightful experience.

10.0 out of 10, Exceptional, (2)
"Communication with this host is the best we’ve had. "
The price is NZ$131
includes taxes & fees
19 Aug - 20 Aug
Zillion’s ville. Delightful experience.

Winnipeg Radiant Home - A peaceful neighborhood with separate entrance

8.8 out of 10, Excellent, (3)
"The suite was located on a quiet street but close to a main street so it was easy getting around. It was sparsely furnished and could have used extra bath towels, face clothes, and blankets. The floor under the bed needs be to be thoroughly cleaned. Considering the affordable cost, it was a good value overall."
The price is NZ$145
includes taxes & fees
27 July - 28 July
Winnipeg Radiant Home - A peaceful neighborhood with separate entrance

Elegant bedroom in Winnipeg

The price is NZ$160
includes taxes & fees
20 July - 21 July
Elegant bedroom in Winnipeg

Mary's Luxury Suite

8.0 out of 10, Very good, (1)
"The suite was very nice, very clean. We were disappointed with cell service ( as I needed it for work). Outside walk way will be good but needs something to keep surrounding rocks off the sidewalk. We suggest a door to separate suite off the bottom of the stairs. It appears the host did not minamalize the amount of noise in the am. Host responded to cell service question promply"
The price is NZ$261
includes taxes & fees
19 Aug - 20 Aug
Mary's Luxury Suite

Private Cozy 1 Bedroom Basement Suite

10.0 out of 10, Exceptional, (2)
"Bon accueil, propre, tranquille. "
The price is NZ$184
includes taxes & fees
28 July - 29 July
Private Cozy 1 Bedroom Basement Suite

Afan Home of Joy

9.8 out of 10, Exceptional, (14)
"We enjoyed our 4-day stay, it was very clean, in a new home, quiet and spacious, and our hosts were very accomodating."
The price is NZ$209
includes taxes & fees
24 July - 25 July
Afan Home of Joy

Cozy Haven 1-bedroom suite close to centre of Winnipeg

10.0 out of 10, Exceptional, (2)
"Would definitely stay here again if I’m ever in Winnipeg! "
The price is NZ$169
includes taxes & fees
27 July - 28 July
Cozy Haven 1-bedroom suite close to centre of Winnipeg

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

10.0 out of 10, Exceptional, (2)
"This property had everything we needed. It felt like home when we arrived. Very clean, comfortable and great location. The management team was quick to respond to any of my needs. I definitely would consider booking in the future. "
The price is NZ$368
includes taxes & fees
20 July - 21 July
*Cozy & Spacious | Free Parking | 15 min Downtown*

3 floors character house

9.4 out of 10, Exceptional, (63)
"Property was clean and owner worked hard to accommodate us. Would recommend this place."
The price is NZ$258
includes taxes & fees
23 July - 24 July
3 floors character house

Welcoming Private 2 Bedroom Suite

9.4 out of 10, Exceptional, (6)
"Fantastic property, excellent hosts! The beds were super comfy, everything we needed was accessible, and the place is in a fantastic location. Would definitely stay again, and highly recommend!"
The price is NZ$210
includes taxes & fees
28 July - 29 July
Welcoming Private 2 Bedroom Suite

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

10.0 out of 10, Exceptional, (3)
"This property is beautiful. The owner is top hostess she went above and beyond for us. Will definitely being staying here again"
The price is NZ$905
includes taxes & fees
20 July - 21 July
🌎Modern 3 bedroom home w/street park’n close to ✈️

Luxury: Home Away from Home with Private Entrance

The price is NZ$204
includes taxes & fees
29 July - 30 July
Luxury: Home Away from Home with Private Entrance

Charming 2-bedroom basement in brilliant Winnipeg with WiFi, AC

10.0 out of 10, Exceptional, (2)
"We had a nice week-long stay in Winnipeg at this Vrbo. The host was easy to communicate with. The suite covered all the basics needed. Thank you."
The price is NZ$244
includes taxes & fees
22 July - 23 July
Charming 2-bedroom basement in brilliant Winnipeg with WiFi, AC

Separate Entrance Basement Suite

8.4 out of 10, Very good, (6)
"Absolutely amazing, clean and had everything we needed. One of my best short term rentals to date."
Separate Entrance Basement Suite

The Snug Spot,Retreat offers a warm and inviting escape for travelers.

The price is NZ$137
includes taxes & fees
4 Aug - 5 Aug
The Snug Spot,Retreat offers a warm and inviting escape for travelers.

Cozy & Stylish 2BR Apartment

The price is NZ$375
includes taxes & fees
23 July - 24 July
Cozy & Stylish 2BR Apartment
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

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?

Cheerful Tuxedo House with Hot Tub : This holiday home rental outside of Headingley offers a fireplace, 1 hot tub and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that 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 Softball Complex 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.