Headingley Holiday Rentals from AU$148: Search Short-Term Rentals

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Our top choices for Headingley holiday rentals

A two-story house with a grey garage door, a covered driveway, and a wooden fence in the background.

1. Prairie Luxury 1 Bedrooms Home

Fort Garry

Carol M.

includes taxes & fees

3 Nov - 4 Nov

A wooden staircase with a modern design, leading to a dark-colored landing area.

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

Fort Garry

Vijaya Shree

includes taxes & fees

16 Nov - 17 Nov

A modern two-story building with a concrete staircase leading to a white door marked with the number 474.

3. The Cozy Corner Home

East Kildonan

includes taxes & fees

3 Nov - 4 Nov

A modern lobby with leather sofas, a glass coffee table, and abstract wall art.

4. Cozy 1 Bedroom Apt In Heart Of Downtown Winnipeg

Downtown Winnipeg

Tina

includes taxes & fees

8 Nov - 9 Nov

5. The Abode family space

Fort Garry

includes taxes & fees

10 Nov - 11 Nov

A modern living room with a leather sofa set, a glass coffee table, and a lamp.

6. Canada Life Centre° Osborne Location

Osborne Village

Billie F.

includes taxes & fees

5 Nov - 6 Nov

A residential driveway with a circular brick pattern leading to a garage.

7. Golden Eagle, Basement Suite

Winnipeg

nathalie

includes taxes & fees

3 Nov - 4 Nov

A modern interior with a wooden staircase, a dining area with a chandelier, and a white cabinet.

8. Upscale Tuxedo Family Retreat with Hot Tub

Tuxedo

Kayla G.

includes taxes & fees

9 Nov - 10 Nov

A modern kitchen with a central island, a dining area with a table and chairs, and a living room with a sofa and a TV.

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

Fort Garry

Reuben S.

includes taxes & fees

16 Nov - 17 Nov

A kitchen with white cabinets, a marble backsplash, and three abstract paintings on the wall.

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

Central St. Boniface

Jordanna C.

includes taxes & fees

3 Nov - 4 Nov

A room with two white upholstered chairs, a dark carpet, and large windows with a view of trees and buildings.

11. Retraite Saint Boniface/St. Boniface Retreat

Central St. Boniface

jenn

includes taxes & fees

12 Nov - 13 Nov

A modern conference room with a glass table, black chairs, a large flat-screen TV, and a decorative plant.

12. Welcoming Private 2 Bedroom Suite

Fort Garry

Vince

includes taxes & fees

6 Nov - 7 Nov

A living room with a flat-screen TV, a sofa, a dining table, and a plant.

13. HOME AWAY FROM HOME

Fort Garry

Diane C.

A spacious indoor area with high ceilings, exposed brick walls, and a central wooden table.

14. FREE PARKING NY Style Condo in Exchange District

Exchange District

Alyssa

includes taxes & fees

5 Nov - 6 Nov

A hotel room with a bed, a desk, a chair, a lamp, a TV, and a window with curtains.

15. Affordable Bachelor Near HSC & Downtown

West Alexander

MARIO

includes taxes & fees

16 Nov - 17 Nov

A staircase with dark wooden steps leading up to a landing.

16. Home away from home! Entire basement suite with privacy and driveway parking!

Fort Garry

Rayna

includes taxes & fees

17 Nov - 18 Nov

A bedroom with a bed, a television displaying a movie, and a wardrobe.

17. Mary's Luxury Suite

Fort Garry

kevin

includes taxes & fees

3 Nov - 4 Nov

A compact kitchen with a central island, a dining area with bar stools, and a black leather sofa.

18. Serene 3 Bed Room Near Airport/Polo Park Main Floor Bedroom

Weston

Charmaine

includes taxes & fees

4 Nov - 5 Nov

A resort with a central pool, wooden cabins, and a mountainous backdrop.

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

Deer Lodge

Renee A.

includes taxes & fees

3 Nov - 4 Nov

A residential building with a stone facade, a front door, and a set of concrete steps leading to a driveway.

20. Clean and Comfortable Home

Fort Garry

includes taxes & fees

3 Nov - 4 Nov

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Top Headingley Hotel Reviews

Birchwood Inn, BW Premier Collection

10/10 Excellent

"Love the pool area"

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$148 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.

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Check prices for these dates

Our top choices for Headingley holiday rentals

1. Prairie Luxury 1 Bedrooms Home

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

3. The Cozy Corner Home

4. Cozy 1 Bedroom Apt In Heart Of Downtown Winnipeg

5. The Abode family space

6. Canada Life Centre° Osborne Location

7. Golden Eagle, Basement Suite

8. Upscale Tuxedo Family Retreat with Hot Tub

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

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

11. Retraite Saint Boniface/St. Boniface Retreat

12. Welcoming Private 2 Bedroom Suite

13. HOME AWAY FROM HOME

14. FREE PARKING NY Style Condo in Exchange District

15. Affordable Bachelor Near HSC & Downtown

16. Home away from home! Entire basement suite with privacy and driveway parking!

17. Mary's Luxury Suite

18. Serene 3 Bed Room Near Airport/Polo Park Main Floor Bedroom

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

20. Clean and Comfortable Home

Find holiday rentals that suit your style

Top Headingley Hotel Reviews

Birchwood Inn, BW Premier Collection

Lakeview Signature, Trademark Collection by Wyndham

Sandman Hotel & Suites Winnipeg Airport

Mere Hotel

Canad Inns Destination Centre Fort Garry

Comfort Inn Winnipeg Airport

Best Western Plus Winnipeg West

Canad Inns Destination Centre Windsor Park

Viscount Gort Hotel

Find out more about Headingley

Frequently asked questions

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