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Holiday Rentals in Headingley

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Our top choices for Headingley holiday rentals

1. Cozy 2BR Suite • Private Entry • Free Parking• self check-in

Cozy 2BR Suite • Private Entry • Free Parking• self check-in
Peguis
The price is €102
includes taxes & fees
5 Sept - 6 Sept
Cozy 2BR Suite • Private Entry • Free Parking• self check-in

2. Lakeview 2 Bedroom Walkout Suite with Trail View

Lakeview 2 Bedroom Walkout Suite with Trail View
Fort Garry
Lakeview 2 Bedroom Walkout Suite with Trail View

3. COZY MIDTOWN HOME

COZY MIDTOWN HOME
St. Vital
The price is €129
includes taxes & fees
5 Sept - 6 Sept
COZY MIDTOWN HOME

4. Exclusive Home Near Concordia, Patio, BBQ, Parking

Exclusive Home Near Concordia, Patio, BBQ, Parking
East Kildonan
The price is €186
includes taxes & fees
6 Sept - 7 Sept
Exclusive Home Near Concordia, Patio, BBQ, Parking

5. De Executive Luxury Home

De Executive Luxury Home
Fort Garry
De Executive Luxury Home

6. Relax at Home

Relax at Home
Fort Garry
The price is €129
includes taxes & fees
6 Sept - 7 Sept
Relax at Home

7. Cozy & spacious space to relax located in a peaceful neighbourhood

Cozy & spacious space to relax located in a peaceful neighbourhood
Fort Garry
The price is €120
includes taxes & fees
19 Aug - 20 Aug
Cozy & spacious space to relax located in a peaceful neighbourhood

8. 2 Bedroom Suite in Transcona Winnipeg

2 Bedroom Suite in Transcona Winnipeg
Transcona
The price is €110
includes taxes & fees
20 Aug - 21 Aug
2 Bedroom Suite in Transcona Winnipeg

9. The Guest Expertise – Where Elegance Meets Comfort in a 5BR Luxury Retreat

The Guest Expertise – Where Elegance Meets Comfort in a 5BR Luxury Retreat
Winnipeg
8.0 out of 10, Very good, (4 reviews)
"This property suited us well for a business meeting to the city! Very nice neighborhood "
Canada
Marilee K.
The price is €336
includes taxes & fees
17 Aug - 18 Aug
The Guest Expertise – Where Elegance Meets Comfort in a 5BR Luxury Retreat

10. 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 €141
includes taxes & fees
6 Sept - 7 Sept
HOME AWAY FROM HOME

11. 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
10.0 out of 10, Exceptional, (1 review)
"I liked most things with this property. We were a bit worried about the location as it was in a less than desirable neighbourhood. Having said that, the manager was wonderful and always willing to help. The neighbours across the road were friendly and helpful. There are security cameras and lots of light so coming home late was not an issue. All in all, I believe we got a fair and good deal."
Canada
Brenda
The price is €159
includes taxes & fees
6 Sept - 7 Sept
Northside Comfort! Pet Friendly Budget Rental close to HSC and The Forks!!!

12. 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 €110
includes taxes & fees
17 Aug - 18 Aug
Separate Entrance Basement Suite

13. Basement Suite on Osborne

Basement Suite on Osborne
Lord Roberts
9.2 out of 10, Wonderful, (9 reviews)
"Parking was easy "
United States
Pamela G.
Basement Suite on Osborne

14. Fully Furnished Basement Unit – Private Entrance Included

Fully Furnished Basement Unit – Private Entrance Included
St. Vital
9.2 out of 10, Wonderful, (14 reviews)
"Great clean spot"
United States
Dustin
The price is €93
includes taxes & fees
8 Aug - 9 Aug
Fully Furnished Basement Unit – Private Entrance Included

15. Duniques unique home Fully furnished 2 bedroom basement suite

Duniques unique home Fully furnished 2 bedroom basement suite
Fort Garry
8.0 out of 10, Very good, (1 review)
"Very nice quiet place to stay."
Canada
Lisa W.
The price is €100
includes taxes & fees
8 Aug - 9 Aug
Duniques unique home Fully furnished 2 bedroom basement suite

16. Canada Life Centre° Osborne Location

Canada Life Centre° Osborne Location
Osborne Village
9.8 out of 10, Exceptional, (6 reviews)
"The location is very good! It is in Osborne area but not at Canada life centre. It was a very good size and well furnished!"
Canada
Celine
The price is €137
includes taxes & fees
9 Aug - 10 Aug
Canada Life Centre° Osborne Location

17. One-bedroom guest suite with private entry

One-bedroom guest suite with private entry
East Kildonan
9.8 out of 10, Exceptional, (9 reviews)
"Clean, quiet, safe community, felt like home."
Canada
Sheri
The price is €90
includes taxes & fees
14 Aug - 15 Aug
One-bedroom guest suite with private entry

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

Cozy Haven 1-bedroom suite close to centre of Winnipeg
Winnipeg
8.8 out of 10, Excellent, (3 reviews)
"Would definitely stay here again if I’m ever in Winnipeg! "
Canada
Ashton P.
The price is €96
includes taxes & fees
5 Sept - 6 Sept
Cozy Haven 1-bedroom suite close to centre of Winnipeg

19. Retraite Saint Boniface/St. Boniface Retreat

Retraite Saint Boniface/St. Boniface Retreat
Central St. Boniface
9.8 out of 10, Exceptional, (10 reviews)
"Great neighborhood and great place to stay "
Canada
jenn
The price is €177
includes taxes & fees
8 Aug - 9 Aug
Retraite Saint Boniface/St. Boniface Retreat

20. Prairie Luxury 1 Bedrooms Home

Prairie Luxury 1 Bedrooms Home
Fort Garry
9.4 out of 10, Exceptional, (9 reviews)
"Enjoyed my 3 night stay very much here! The property was exceptionally clean and modern! It was also very easy to communicate with the owner regarding check in and check out rules! Great and safe location."
Canada
Emma
The price is €150
includes taxes & fees
12 Aug - 13 Aug
Prairie Luxury 1 Bedrooms Home
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, 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 €93 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?

Stormwater Haven: Peaceful, Stylish and comfortable space in South Winnipeg.: This holiday home rental outside of Headingley is equipped with a fireplace, air conditioning and WiFi to help you feel comfortable during your stay. Kitchen amenities such as an oven and a microwave can make your holiday run smoothly.

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.