Headingley Holiday Rentals

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Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

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$385
HK$1,067 total
includes taxes & fees
24 Mar - 25 Mar
Kelvista's suite
Smart TV, fireplace

Separate Entrance Basement Suite

Separate Entrance Basement Suite
Fort Garry
8.0 out of 10, Very good, (11 reviews)
"Very good services."
Canada
Alabi A.
The price is HK$642
HK$932 total
includes taxes & fees
24 Mar - 25 Mar
Separate Entrance Basement Suite
Interior

Cheerful Tuxedo House with Hot Tub

Cheerful Tuxedo House with Hot Tub
Tuxedo
9.8 out of 10, Exceptional, (40 reviews)
"We totally enjoyed our stay!"
Canada
peter S.
The price is HK$2,169
HK$5,287 total
includes taxes & fees
26 Mar - 27 Mar
Cheerful Tuxedo House with Hot Tub
Smart TV, fireplace

Private Basement Apartment with separate entrance

Private Basement Apartment with separate entrance
St. Vital
10.0 out of 10, Exceptional, (1 review)
"Perfect for a 1 night stay. Just passing through. "
Canada
Norman
The price is HK$628
HK$1,010 total
includes taxes & fees
24 Mar - 25 Mar
Private Basement Apartment with separate entrance
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$628
HK$983 total
includes taxes & fees
24 Mar - 25 Mar
Cozy Home away from Home in a Basement with a separate entrance
Pool

Modern house in trendy location in South Winnipeg-Bridgwater Area

Modern house in trendy location in South Winnipeg-Bridgwater Area
Fort Garry
10.0 out of 10, Exceptional, (30 reviews)
"One of the most well stocked places we have ever stayed. Very nice place in a good area. Would definitely stay again! "
Canada
Jayme J.
Modern house in trendy location in South Winnipeg-Bridgwater Area
Property grounds

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 reviews)
"We had a great stay! Hosts were communicative and we have nothing but good things to say about property itself."
Canada
Aidan M.
The price is HK$437
HK$892 total
includes taxes & fees
24 Mar - 25 Mar
2 LUXURY BEDROOM IN BASEMENT FOR 4 PEOPLE !!!
Exterior

Golden Eagle, Basement Suite

Golden Eagle, Basement Suite
Winnipeg
9.8 out of 10, Exceptional, (6 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 HK$411
HK$828 total
includes taxes & fees
26 Mar - 27 Mar
Golden Eagle, Basement Suite
Dining

Welcoming Private 2 Bedroom Suite

Welcoming Private 2 Bedroom Suite
Fort Garry
9.2 out of 10, Wonderful, (12 reviews)
"The place is clean and the host was a call away and gave us their info in case we need help. "
Canada
Mila D.
The price is HK$428
HK$1,017 total
includes taxes & fees
24 Mar - 25 Mar
Welcoming Private 2 Bedroom Suite
Fridge, microwave, oven, stovetop

*New & Modern Home | Free Parking | 5 mins Downtown*

*New & Modern Home | Free Parking | 5 mins Downtown*
Norwood East
9.8 out of 10, Exceptional, (7 reviews)
"Great place"
Canada
Blaine
The price is HK$715
HK$1,619 total
includes taxes & fees
24 Mar - 25 Mar
*New & Modern Home | Free Parking | 5 mins Downtown*
Interior

Serenity meets class: Entire Basement Suite in Winnipeg

Serenity meets class: Entire Basement Suite in Winnipeg
St. Vital
9.2 out of 10, Wonderful, (14 reviews)
"We had a great stay. The host was prompt to answer questions and the space was perfect for a weekend getaway. "
Canada
Lonna
The price is HK$334
HK$737 total
includes taxes & fees
24 Mar - 25 Mar
Serenity meets class: Entire Basement Suite in Winnipeg
Property grounds

Luxury: Home Away from Home with Private Entrance

Luxury: Home Away from Home with Private Entrance
Transcona
8.6 out of 10, Excellent, (4 reviews)
"Nice suite, clean and relatively new. some defects pointed out to the owner and very receptive of comments."
Canada
Bill H.
The price is HK$285
HK$915 total
includes taxes & fees
28 Mar - 29 Mar
Luxury: Home Away from Home with Private Entrance
Exterior

Prairie Luxury 2 Bedrooms Home

Prairie Luxury 2 Bedrooms Home
Fort Garry
9.4 out of 10, Exceptional, (6 reviews)
"Great place. Easy, convenient location. Clean and spacious."
Canada
Randy H.
The price is HK$483
HK$1,573 total
includes taxes & fees
24 Mar - 25 Mar
Prairie Luxury 2 Bedrooms Home
Interior

Retraite Saint Boniface/St. Boniface Retreat

Retraite Saint Boniface/St. Boniface Retreat
Central St. Boniface
9.8 out of 10, Exceptional, (7 reviews)
"Great neighborhood and great place to stay "
Canada
jenn
The price is HK$856
HK$1,603 total
includes taxes & fees
24 Mar - 25 Mar
Retraite Saint Boniface/St. Boniface Retreat
Exterior detail

Private Cozy 1 Bedroom Basement Suite

Private Cozy 1 Bedroom Basement Suite
Fort Garry
9.2 out of 10, Wonderful, (5 reviews)
"Nice clean place to stay"
United States
Thomas B.
The price is HK$514
HK$983 total
includes taxes & fees
24 Mar - 25 Mar
Private Cozy 1 Bedroom Basement Suite
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$360
HK$1,037 total
includes taxes & fees
24 Mar - 25 Mar
Mary's Luxury Suite
Smart TV

Fully Furnished Basement Unit – Private Entrance Included

Fully Furnished Basement Unit – Private Entrance Included
St. Vital
8.8 out of 10, Excellent, (9 reviews)
"Nice place "
Canada
hanad m.
The price is HK$542
HK$814 total
includes taxes & fees
23 Apr - 24 Apr
Fully Furnished Basement Unit – Private Entrance Included
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)
"Nice and well take care of place, host was very helpful and kind, highly recommended, for my first time in Winnipeg was easy access, convenient and close to the area I needed to be. "
Canada
Gabriela V.
The price is HK$352
HK$725 total
includes taxes & fees
24 Mar - 25 Mar
One-bedroom guest suite with private entry
Exterior

Elegant 1-Bedroom Basement Suite

Elegant 1-Bedroom Basement Suite
St. Vital
9.6 out of 10, Exceptional, (4 reviews)
"Well maintained clean property. The owner of the home was very accomodating and kind. Great location. Felt like home during our stay! Will definitely come back."
Canada
Sameh
The price is HK$360
HK$868 total
includes taxes & fees
24 Mar - 25 Mar
Elegant 1-Bedroom Basement Suite
Interior

Restful Haven

Restful Haven
Fort Garry
The price is HK$514
HK$983 total
includes taxes & fees
24 Mar - 25 Mar
Restful Haven
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

8/10 Good
"Decent hotel for having an early flight out. There was a lot of kids running down the hallways past 11 pm but can't blame the hotel for bad parents. "
Jodi 1-night trip
Posted 4 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:

  • View our selection of featured holiday rentals in Headingley
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  • Enter your travel dates to view the best deals on holiday rentals in Headingley while they last

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?

3 floors character house: This holiday home rental outside of Headingley is located in the city centre, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

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.