Holiday Rentals in Headingley

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Headingley holiday rentals

A living room with a black sofa, a glass coffee table, a potted plant, a flat-screen TV, and a wall-mounted clock.

1. Cozy Haven 1-bedroom suite close to centre of Winnipeg

Cozy Haven 1-bedroom suite close to centre of Winnipeg
Winnipeg
8.6 out of 10, Excellent, (4 reviews)
"Would definitely stay here again if I’m ever in Winnipeg! "
Canada
Ashton P.
The price is €83
includes taxes & fees
14 Nov - 15 Nov
Cozy Haven 1-bedroom suite close to centre of Winnipeg
A modern living room with a leather sofa set, a glass coffee table, and a lamp.

2. Canada Life Centre° Osborne Location

Canada Life Centre° Osborne Location
Osborne Village
9.8 out of 10, Exceptional, (7 reviews)
"Perfect stay for 5 nights with my daughter. I would stay here again. "
Canada
Billie F.
The price is €130
includes taxes & fees
21 Nov - 22 Nov
Canada Life Centre° Osborne Location
A two-story house with a grey garage door, a covered driveway, and a wooden fence in the background.

3. Prairie Luxury 1 Bedrooms Home

Prairie Luxury 1 Bedrooms Home
Fort Garry
9.2 out of 10, Wonderful, (12 reviews)
"Wonderful stay! Clean and comfortable. Great hosts. I would definitely stay again. "
Canada
Carol M.
The price is €135
includes taxes & fees
12 Nov - 13 Nov
Prairie Luxury 1 Bedrooms Home
A residential exterior with a wooden gate, a concrete step leading to a door, and a welcome mat.

4. The Peaceful Lower Loft Where Comfort Meets Quiet Escape.

The Peaceful Lower Loft Where Comfort Meets Quiet Escape.
Fort Garry
9.4 out of 10, Exceptional, (3 reviews)
"Full privacy, had a peaceful stay. I highly recommend if anyone is looking for a quiet peaceful stay."
Canada
Vijaya Shree
The price is €84
includes taxes & fees
23 Nov - 24 Nov
The Peaceful Lower Loft Where Comfort Meets Quiet Escape.
A modern living room with a large flat-screen TV mounted on a dark wall, a white entertainment unit with decorative items, and a marble-like textured wall.

5. One-bedroom guest suite with private entry

One-bedroom guest suite with private entry
East Kildonan
9.4 out of 10, Exceptional, (11 reviews)
"The suite was spacious and well equipped."
United States
Michael G.
The price is €85
includes taxes & fees
8 Dec - 9 Dec
One-bedroom guest suite with private entry
A modern two-story building with a concrete staircase leading to a white door marked with the number 474.

6. The Cozy Corner Home

The Cozy Corner Home
2.0 star property
East Kildonan
The price is €106
includes taxes & fees
12 Nov - 13 Nov
The Cozy Corner Home
A modern conference room with a glass table, black chairs, a large flat-screen TV, and a decorative plant.

7. Welcoming Private 2 Bedroom Suite

Welcoming Private 2 Bedroom Suite
Fort Garry
9.6 out of 10, Exceptional, (19 reviews)
"Our overall stay was so smooth, owner provided a clean, tidy, well lit place to stay and responsive to our queries. Well recommended!"
Canada
Charmie Therese
The price is €107
includes taxes & fees
12 Nov - 13 Nov
Welcoming Private 2 Bedroom Suite
A hotel room with a bed, a desk, a chair, a lamp, a TV, and a window with curtains.

8. Affordable Bachelor Near HSC & Downtown

Affordable Bachelor Near HSC & Downtown
West Alexander
8.0 out of 10, Very good, (1 review)
"No bathtub. Parking was a headache as others kept parking in my spot."
Canada
MARIO
The price is €125
includes taxes & fees
23 Nov - 24 Nov
Affordable Bachelor Near HSC & Downtown
A building exterior with a textured facade, a door, and a mailbox.

9. Private Cozy 1 Bedroom Basement Suite

Private Cozy 1 Bedroom Basement Suite
Fort Garry
9.4 out of 10, Exceptional, (6 reviews)
"Nice clean place to stay"
United States
Thomas B.
Private Cozy 1 Bedroom Basement Suite
A covered patio area with a wooden deck, a white lounge chair, a table, and a hanging flower basket.

10. Maryland Homestay - Downtown Apartment #1

Maryland Homestay - Downtown Apartment #1
Winnipeg
8.0 out of 10, Very good, (7 reviews)
"Yes, you can walk to get everything you need. "
Canada
Allen
The price is €102
includes taxes & fees
10 Dec - 11 Dec
Maryland Homestay - Downtown Apartment #1
A spacious indoor area with high ceilings, exposed brick walls, and a central wooden table.

11. FREE PARKING NY Style Condo in Exchange District

FREE PARKING NY Style Condo in Exchange District
Exchange District
10.0 out of 10, Exceptional, (97 reviews)
"Lovely stay - very spacious, secure and clean! Would recommend"
Canada
Alyssa
The price is €134
includes taxes & fees
16 Nov - 17 Nov
FREE PARKING NY Style Condo in Exchange District
A modern hallway with a wardrobe, a kitchen area with a refrigerator, and a seating area with a sofa.

12. Peaceful and spacious one bed and rec-room for short or long stay

Peaceful and spacious one bed and rec-room for short or long stay
Fort Garry
Peaceful and spacious one bed and rec-room for short or long stay
A two-story house with a garage, stone accents, and a clear blue sky.

13. Elegant 1-Bedroom Basement Suite

Elegant 1-Bedroom Basement Suite
St. Vital
9.2 out of 10, Wonderful, (9 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 €99
includes taxes & fees
13 Nov - 14 Nov
Elegant 1-Bedroom Basement Suite
A modern living room with a sectional sofa, a coffee table, a TV mounted on the wall, and a fireplace.

14. 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.
Separate Entrance Basement Suite
A dining area with a round table, chairs, and a vase of flowers.

15. Stormwater Haven: Peaceful, Stylish and comfortable space in South Winnipeg.

Stormwater Haven: Peaceful, Stylish and comfortable space in South Winnipeg.
Fort Garry
8.6 out of 10, Excellent, (9 reviews)
"Newly renovated, convenient location"
Canada
paula
The price is €84
includes taxes & fees
12 Nov - 13 Nov
Stormwater Haven: Peaceful, Stylish and comfortable space in South Winnipeg.
A residential driveway with a circular brick pattern leading to a garage.

16. Golden Eagle, Basement Suite

Golden Eagle, Basement Suite
Winnipeg
9.2 out of 10, Wonderful, (20 reviews)
"It was a great stay! Quiet and comfortable, host was always nice."
United States
nathalie
The price is €113
includes taxes & fees
12 Nov - 13 Nov
Golden Eagle, Basement Suite
A bedroom with a bed, a television displaying a movie, and a wardrobe.

17. Mary's Luxury Suite

Mary's Luxury Suite
Fort Garry
8.4 out of 10, Very good, (5 reviews)
"Good"
United States
kevin
Mary's Luxury Suite
A modern interior with a wooden staircase, a dining area with a chandelier, and a white cabinet.

18. Upscale Tuxedo Family Retreat with Hot Tub

Upscale Tuxedo Family Retreat with Hot Tub
Tuxedo
9.8 out of 10, Exceptional, (48 reviews)
"Great house in a great location! Host was very responsive. Would highly recommend!"
United States
Kayla G.
The price is €683
includes taxes & fees
12 Nov - 13 Nov
Upscale Tuxedo Family Retreat with Hot Tub
Interior

19. Cozy Nest - 1 Bedroom

Cozy Nest - 1 Bedroom
St. Vital
10.0 out of 10, Exceptional, (2 reviews)
"Very private, super new and super clean, convenient location and GREAT air conditioning."
Canada
Karryn
The price is €112
includes taxes & fees
13 Nov - 14 Nov
Cozy Nest - 1 Bedroom
A compact living space with a kitchenette, a flat-screen TV, a sofa, and a coffee maker.

20. Serenity meets class: Entire Basement Suite in Winnipeg

Serenity meets class: Entire Basement Suite in Winnipeg
St. Vital
9.4 out of 10, Exceptional, (36 reviews)
"It was quiet, private, clean and access to a washer and dryer was a definite plus. Amy questions we had were answered in a timely and throughout manner."
Canada
Carla
Serenity meets class: Entire Basement Suite in Winnipeg
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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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, apart-hotels, 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 €74 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?

St B. Living : This holiday home rental outside of Headingley is equipped with a balcony, air conditioning and laundry facilities to help you feel comfortable during your stay. 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.

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.