Headingley Holiday Rentals

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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for Headingley holiday rentals

Exterior detail

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 HK$486
HK$1,187 total
includes taxes & fees
26 May - 27 May
Kelvista's suite
Exterior

Golden Eagle, Basement Suite

Golden Eagle, Basement Suite
Winnipeg
9.8 out of 10, Exceptional, (8 reviews)
"It was very clean and comfortable!!"
Canada
Daryll D.
The price is HK$432
HK$853 total
includes taxes & fees
25 May - 26 May
Golden Eagle, Basement Suite
Smart TV, fireplace

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

Cozy Home away from Home in a Basement with a separate entrance
St. Vital
9.2 out of 10, Wonderful, (10 reviews)
"Check in was easy, place was nice."
Canada
Blair J.
The price is HK$629
HK$984 total
includes taxes & fees
14 May - 15 May
Cozy Home away from Home in a Basement with a separate entrance
Smart TV

Northside Comfort! Pet Friendly Budget Rental close to HSC and The Forks!!!

Northside Comfort! Pet Friendly Budget Rental close to HSC and The Forks!!!
Winnipeg
The price is HK$772
HK$1,424 total
includes taxes & fees
17 May - 18 May
Northside Comfort! Pet Friendly Budget Rental close to HSC and The Forks!!!
Pool

*1min Riverview Health 7min Downtown Free Parking

*1min Riverview Health 7min Downtown Free Parking
Winnipeg
9.2 out of 10, Wonderful, (11 reviews)
"Very clean. Bedrooms all on lower level- it worked out well when you have people getting up at different times in the morning. 2 1/2 bathrooms, ideal for when everyone’s trying to get ready and leave at the same time. I would stay again "
Canada
Susan G.
The price is HK$649
HK$1,520 total
includes taxes & fees
18 May - 19 May
*1min Riverview Health 7min Downtown Free Parking
Exterior detail

Cozy Basement Suite in Winnipeg

Cozy Basement Suite in Winnipeg
St. Vital
8.0 out of 10, Very good, (2 reviews)
"Great host, great amenities "
United States
Alyce M.
The price is HK$514
HK$1,120 total
includes taxes & fees
20 May - 21 May
Cozy Basement Suite in Winnipeg
Smart TV, fireplace

Separate Entrance Basement Suite

Separate Entrance Basement Suite
Fort Garry
8.0 out of 10, Very good, (11 reviews)
"Very clean beautiful place. Very comfy for a great price would recommend "
United States
Addy F.
The price is HK$643
HK$934 total
includes taxes & fees
25 May - 26 May
Separate Entrance Basement Suite
Living area

Modern Luxury in Richmond West

Modern Luxury in Richmond West
Fort Garry
10.0 out of 10, Exceptional, (1 review)
"Très propre et très spacieux;dans un quartier très calme et très sécuritaire. Idéal pour les familles.je le recommande vivement. Merci encore à l’hôte."
Canada
Christian Martial
The price is HK$1,260
HK$1,873 total
includes taxes & fees
10 Jun - 11 Jun
Modern Luxury in Richmond West
Smart TV

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 HK$429
HK$883 total
includes taxes & fees
14 May - 15 May
Exquisite 1-bedroom basement in the quiet neighbourhood of Bonavista, Winnipeg
Property grounds

Luxury: Home Away from Home with Private Entrance

Luxury: Home Away from Home with Private Entrance
Transcona
8.8 out of 10, Excellent, (5 reviews)
"This was a great stay! Very clean and easy process, host was very quick to answer questions 👍"
Canada
Owen
The price is HK$286
HK$917 total
includes taxes & fees
19 May - 20 May
Luxury: Home Away from Home with Private Entrance
Smart TV

HOME AWAY FROM HOME

HOME AWAY FROM HOME
Fort Garry
10.0 out of 10, Exceptional, (3 reviews)
"This apartment was perfect for the two of us! Nice, clean and the bed was incredibly comfortable! Easy check in and check out! "
Canada
Tania
The price is HK$538
HK$1,282 total
includes taxes & fees
15 May - 16 May
HOME AWAY FROM HOME
TV

Cozy Winnipeg Retreat

Cozy Winnipeg Retreat
Peguis
10.0 out of 10, Exceptional, (1 review)
"Basement of a house. Super clean, quiet people that live above, good price :)"
Canada
Jaymee
The price is HK$437
HK$826 total
includes taxes & fees
25 May - 26 May
Cozy Winnipeg Retreat
Exterior detail

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 HK$457
HK$1,052 total
includes taxes & fees
24 May - 25 May
Charming Bedroom in Bonavista
TV, fireplace

Basement Suite on Osborne

Basement Suite on Osborne
Lord Roberts
9.0 out of 10, Wonderful, (8 reviews)
"When we come back to Winnipeg we would definitely like to stay at this accommodation again. Safe, friendly neighborhood. Great tacos at BMC close by. Safeway close by."
United States
Cynthia B.
The price is HK$514
HK$782 total
includes taxes & fees
19 May - 20 May
Basement Suite on Osborne
Interior

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
9.4 out of 10, Exceptional, (16 reviews)
"Great!"
Canada
Richard
The price is HK$412
HK$802 total
includes taxes & fees
19 May - 20 May
2 Bed rooms|Private entrance|Free Parking|Self-Check-in into our Upscale Haven.
Fridge, microwave, oven, stovetop

Cozy Stay Near Airport|Bright, Clean and Peaceful!

Cozy Stay Near Airport|Bright, Clean and Peaceful!
King Edward
9.6 out of 10, Exceptional, (13 reviews)
"Clean house, comfortable beds, great location!"
Canada
Travis
The price is HK$1,177
HK$2,164 total
includes taxes & fees
26 May - 27 May
Cozy Stay Near Airport|Bright, Clean and Peaceful!
Living area

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 reviews)
"Would definitely stay here again if I’m ever in Winnipeg! "
Canada
Ashton P.
The price is HK$437
HK$792 total
includes taxes & fees
14 May - 15 May
Cozy Haven 1-bedroom suite close to centre of Winnipeg
2 bedrooms, iron/ironing board, WiFi, bed sheets

Mary's Luxury Suite

Mary's Luxury Suite
Fort Garry
9.0 out of 10, Wonderful, (2 reviews)
"It was great and wanted to apologize for the in and out, my son vapes so he kelp going in and out. I wasn’t sure which door you were referring to, to leave open. Had a great sleep! And Saskatchewan won so we were happy! Thank you! "
Canada
Patricia S.
The price is HK$514
HK$1,255 total
includes taxes & fees
17 May - 18 May
Mary's Luxury Suite
1 bedroom, desk, iron/ironing board, free WiFi

Spacious 1 Bed/1 Bath near HSC and Downtown *Sleeps 4 and Free Parking

Spacious 1 Bed/1 Bath near HSC and Downtown *Sleeps 4 and Free Parking
West Alexander
10.0 out of 10, Exceptional, (1 review)
"This was a perfect location if you have appointments at the Health Sciences Center. 5-10min walk to the William Street Entrance. Quiet location, comfortable apartment."
Canada
Jennifer
The price is HK$520
HK$1,430 total
includes taxes & fees
20 May - 21 May
Spacious 1 Bed/1 Bath near HSC and Downtown *Sleeps 4 and Free Parking
Interior

One-bedroom guest suite with private entry

One-bedroom guest suite with private entry
East Kildonan
9.8 out of 10, Exceptional, (7 reviews)
"Clean, quiet, safe community, felt like home."
Canada
Sheri
The price is HK$353
HK$726 total
includes taxes & fees
24 May - 25 May
One-bedroom guest suite with private entry
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
"Room was clean and awesome staff "
Roba 2-night trip
Posted 9 hours ago
Victoria Inn Hotel and Convention Centre Winnipeg

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:

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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?

Cozy Modern Basement Suite in Devonshire 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.