A rural landscape with a field of tall grass, two grain silos, and a wooden barn under a colorful sky.

Headingley Holiday Rentals

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Our top choices for Headingley holiday rentals

1. 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 NZ$640
includes taxes & fees
25 Aug - 26 Aug
The Guest Expertise – Where Elegance Meets Comfort in a 5BR Luxury Retreat

2. Luxury Tuxedo Family Home with Hot Tub

Luxury Tuxedo Family Home with Hot Tub
Tuxedo
9.8 out of 10, Exceptional, (47 reviews)
"Awesome place!!!!!!"
Canada
Reg S.
Luxury Tuxedo Family Home with Hot Tub

3. 6 BEDROOM MAGNIFICENT STYLISH ESCAPE

6 BEDROOM MAGNIFICENT STYLISH ESCAPE
Fort Garry
The price is NZ$2,655
includes taxes & fees
25 Aug - 26 Aug
6 BEDROOM MAGNIFICENT STYLISH ESCAPE

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

🌎Modern 3 bedroom home w/street park’n close to ✈️
Weston
8.0 out of 10, Very good, (4 reviews)
"This property is beautiful. The owner is top hostess she went above and beyond for us. Will definitely being staying here again"
Canada
Aldeana L.
The price is NZ$895
includes taxes & fees
6 Sept - 7 Sept
🌎Modern 3 bedroom home w/street park’n close to ✈️

5. Luxurious House in a Desired Location, King Bed

Luxurious House in a Desired Location, King Bed
Fort Garry
10.0 out of 10, Exceptional, (57 reviews)
"I really enjoy staying here. I’ll be back every April."
Canada
Owein H.
The price is NZ$778
includes taxes & fees
9 Sept - 10 Sept
Luxurious House in a Desired Location, King Bed

6. Spacious new 3 Bedroom, sleeps 10, King Bed, 8min to YWG

Spacious new 3 Bedroom, sleeps 10, King Bed, 8min to YWG
Deer Lodge
The price is NZ$448
includes taxes & fees
27 Aug - 28 Aug
Spacious new 3 Bedroom, sleeps 10, King Bed, 8min to YWG

7. HOME AWAY FROM HOME

HOME AWAY FROM HOME
Fort Garry
9.6 out of 10, Exceptional, (4 reviews)
"Worked well for us"
United States
Diane C.
The price is NZ$275
includes taxes & fees
25 Aug - 26 Aug
HOME AWAY FROM HOME

8. 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, (2 reviews)
"Our stay was excellent, the house was clean and the owner was responsive and great to deal with. Location was great for us."
United States
Brenda R.
The price is NZ$326
includes taxes & fees
25 Aug - 26 Aug
Northside Comfort! Pet Friendly Budget Rental close to HSC and The Forks!!!

9. 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, (37 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.
The price is NZ$664
includes taxes & fees
1 Sept - 2 Sept
Modern house in trendy location in South Winnipeg-Bridgwater Area

10. The Wooden Nest | Your Comfy Relaxing Escape

The Wooden Nest | Your Comfy Relaxing Escape
King Edward
9.4 out of 10, Exceptional, (16 reviews)
"I had a very pleasant stay. The place was clean, comfortable, and well located. I truly enjoyed my stay and would definitely recommend it.”"
Canada
Alyson J.
The price is NZ$406
includes taxes & fees
8 Sept - 9 Sept
The Wooden Nest | Your Comfy Relaxing Escape

11. Northside Comfort 2 !!! Pet Friendly Budget Rental Close to HSC and The Forks

Northside Comfort 2 !!! Pet Friendly Budget Rental Close to HSC and The Forks
Winnipeg
10.0 out of 10, Exceptional, (1 review)
"Excellent stay"
United States
Opeyemi A.
The price is NZ$304
includes taxes & fees
25 Aug - 26 Aug
Northside Comfort 2 !!! 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 NZ$200
includes taxes & fees
2 Sept - 3 Sept
Separate Entrance Basement Suite

13. Beautiful Home In A Prime Location

Beautiful Home In A Prime Location
King Edward
5.0 out of 10, (2 reviews)
"The house itself is a bit rundown which you can’t really tell from the online pictures. Broken towel hangers, broken toilet roll, unpatched wall where thermostat was replaced, ceiling fans difficult to use (remote batteries not working?), etc…these impacted our overall satisfaction with the rental. The location is convenient to the airport.Communication with the host was timely and they did get us extra towels when requested. Check-in was easy. Ample parking on the street. The rental met our...
Canada
Lindsay B.
Beautiful Home In A Prime Location

14. Prairie Luxury 2 Bedrooms Home

Prairie Luxury 2 Bedrooms Home
Fort Garry
9.6 out of 10, Exceptional, (8 reviews)
"Great place. Easy, convenient location. Clean and spacious."
Canada
Randy H.
The price is NZ$315
includes taxes & fees
14 Sept - 15 Sept
Prairie Luxury 2 Bedrooms Home

15. Manhattan Suite

Manhattan Suite
Fort Garry
The price is NZ$218
includes taxes & fees
1 Sept - 2 Sept
Manhattan Suite

16. Retraite Saint Boniface/St. Boniface Retreat

Retraite Saint Boniface/St. Boniface Retreat
Central St. Boniface
9.6 out of 10, Exceptional, (11 reviews)
"Great neighborhood and great place to stay "
Canada
jenn
The price is NZ$340
includes taxes & fees
26 Aug - 27 Aug
Retraite Saint Boniface/St. Boniface Retreat

17. Modern 2 Bedroom Home In A Prime Location

Modern 2 Bedroom Home In A Prime Location
Winnipeg
4.0 out of 10, (1 review)
"The yard was unusable. It had not been mowed since winter.The long grass and weeds were infested with mosquitos, unlike other properties on the street. There were 3 tv’s but only 3 drinking glasses. The house was superficially clean but the vents and baseboards were dirty. 2 bathroom lights were out. The tub was missing some enamel. When we got there the battery in the thermostat was out and the sliding doors for one closet were leaning into the room. Land lord did fix the thermostat and got the...
United States
Sheila T.
The price is NZ$433
includes taxes & fees
25 Aug - 26 Aug
Modern 2 Bedroom Home In A Prime Location

18. Mary's Luxury Suite

Mary's Luxury Suite
Fort Garry
9.4 out of 10, Exceptional, (3 reviews)
"Overall was a great experience. Great communication, lovely, clean and updated little basement apartment which gave a relaxing and cozy feeling. It was exactly what we needed. There was no data connection, which is no fault to the owner but they did have wifi! So that was a win! Overall lovely stay!"
United States
Haley B.
The price is NZ$283
includes taxes & fees
25 Aug - 26 Aug
Mary's Luxury Suite

19. Cozy 2-Bedroom Home in St-Boniface – 5 Min Walk to Food, Fuel & More

Cozy 2-Bedroom Home in St-Boniface – 5 Min Walk to Food, Fuel & More
Central St. Boniface
8.8 out of 10, Excellent, (13 reviews)
"Nice and attractive place … host has good communication "
United States
Benson-Ifere E.
The price is NZ$211
includes taxes & fees
26 Aug - 27 Aug
Cozy 2-Bedroom Home in St-Boniface – 5 Min Walk to Food, Fuel & More

20. 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 NZ$189
includes taxes & fees
26 Aug - 27 Aug
Duniques unique home Fully furnished 2 bedroom basement suite
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, 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 NZ$164 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.