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. 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.
Luxurious House in a Desired Location, King Bed

2. 🌎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 AU$728
includes taxes & fees
19 Sept - 20 Sept
🌎Modern 3 bedroom home w/street park’n close to ✈️

3. 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

4. The Wooden Nest | Your Comfy Relaxing Escape

The Wooden Nest | Your Comfy Relaxing Escape
King Edward
9.6 out of 10, Exceptional, (17 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 AU$360
includes taxes & fees
22 Sept - 23 Sept
The Wooden Nest | Your Comfy Relaxing Escape

5. 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 AU$377
includes taxes & fees
1 Oct - 2 Oct
Spacious new 3 Bedroom, sleeps 10, King Bed, 8min to YWG

6. Cozy house in luxurious Bridgewater area.

Cozy house in luxurious Bridgewater area.
Fort Garry
10.0 out of 10, Exceptional, (1 review)
"This is a very nice 3 bedroom bungalow in a new neighborhood. Beds are comfy, there are lots of extra blankets as well. The host is very accommodating and one thing I loved was that you could pay a little extra for a late checkout. Overall I would recommend this place to anyone"
United States
Sharon W.
The price is AU$284
includes taxes & fees
1 Oct - 2 Oct
Cozy house in luxurious Bridgewater area.

7. Cozy 2-Bedroom Loft in DT! Walking distance to the Forks and Canada Life Centre

Cozy 2-Bedroom Loft in DT! Walking distance to the Forks and Canada Life Centre
Exchange District
9.2 out of 10, Wonderful, (17 reviews)
"Very responsive host and great location! 2 minute walk to the Royal Manitoba Museum and great restaurants nearby! "
Canada
Raequel G.
The price is AU$373
includes taxes & fees
20 Sept - 21 Sept
Cozy 2-Bedroom Loft in DT! Walking distance to the Forks and Canada Life Centre

8. 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 AU$215
includes taxes & fees
21 Sept - 22 Sept
HOME AWAY FROM HOME

9. 6 BEDROOM MAGNIFICENT STYLISH ESCAPE

6 BEDROOM MAGNIFICENT STYLISH ESCAPE
Fort Garry
The price is AU$2,223
includes taxes & fees
1 Oct - 2 Oct
6 BEDROOM MAGNIFICENT STYLISH ESCAPE

10. theLOFTonJAMES, Historic Exchange District, Exposed Brick & Beams, High Ceilings

theLOFTonJAMES, Historic Exchange District, Exposed Brick & Beams, High Ceilings
Exchange District
10.0 out of 10, Exceptional, (69 reviews)
"This place is a 10/10! The owner was extremely helpful and accommodating. The condominium is superb with a great location. "
United States
Gagan
The price is AU$533
includes taxes & fees
16 Oct - 17 Oct
theLOFTonJAMES, Historic Exchange District, Exposed Brick & Beams, High Ceilings

11. STYLISH 2-BEDROOM BASEMENT SUITE.PRIVATE ENTRANCE& PARKING. NEAR U OF M 4GUESTS!

STYLISH 2-BEDROOM BASEMENT SUITE.PRIVATE ENTRANCE& PARKING. NEAR U OF M 4GUESTS!
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 AU$171
includes taxes & fees
18 Oct - 19 Oct
STYLISH 2-BEDROOM BASEMENT SUITE.PRIVATE ENTRANCE& PARKING. NEAR U OF M 4GUESTS!

12. 3-Bedroom Home Near Downtown | Roku Smart TVs in Every Room

3-Bedroom Home Near Downtown | Roku Smart TVs in Every Room
Winnipeg
The price is AU$375
includes taxes & fees
19 Oct - 20 Oct
3-Bedroom Home Near Downtown | Roku Smart TVs in Every Room

13. Cozy two-bedroom retreat in the heart of St. Boniface,

Cozy two-bedroom retreat in the heart of St. Boniface,
Central St. Boniface
10.0 out of 10, Exceptional, (4 reviews)
"Good communication, well located and the property was well described in the ad. Would stay again"
United States
Terry P.
The price is AU$242
includes taxes & fees
24 Sept - 25 Sept
Cozy two-bedroom retreat in the heart of St. Boniface,

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

The Peaceful Lower Loft Where Comfort Meets Quiet Escape.
Fort Garry
10.0 out of 10, Exceptional, (1 review)
"Full privacy, had a peaceful stay. I highly recommend if anyone is looking for a quiet peaceful stay."
Canada
Vijaya Shree
The price is AU$158
includes taxes & fees
28 Sept - 29 Sept
The Peaceful Lower Loft Where Comfort Meets Quiet Escape.

15. Prairie Luxury 1 Bedrooms Home

Prairie Luxury 1 Bedrooms Home
Fort Garry
9.4 out of 10, Exceptional, (11 reviews)
"Wonderful stay! Clean and comfortable. Great hosts. I would definitely stay again. "
Canada
Carol M.
The price is AU$224
includes taxes & fees
22 Sept - 23 Sept
Prairie Luxury 1 Bedrooms Home

16. 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 AU$273
includes taxes & fees
1 Oct - 2 Oct
Northside Comfort! Pet Friendly Budget Rental close to HSC and The Forks!!!

17. Manhattan Suite

Manhattan Suite
Fort Garry
10.0 out of 10, Exceptional, (1 review)
"."
United States
Bill Jenry T.
The price is AU$184
includes taxes & fees
23 Sept - 24 Sept
Manhattan Suite

18. 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 AU$128
includes taxes & fees
21 Sept - 22 Sept
Duniques unique home Fully furnished 2 bedroom basement suite

19. Modern 3bedroom with ensuite bathrooms Lakeview home in Prairie Pointe, winnipeg

Modern 3bedroom with ensuite bathrooms Lakeview home in Prairie Pointe, winnipeg
Fort Garry
9.0 out of 10, Wonderful, (2 reviews)
"The place was spotless and the host was absolutely very courteous. "
Canada
Lilly
The price is AU$674
includes taxes & fees
21 Sept - 22 Sept
Modern 3bedroom with ensuite bathrooms Lakeview home in Prairie Pointe, 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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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 favourite 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 depend 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 AU$117 per night. Entering your travel dates in the search wizard might find you 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.