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

Headingley Vacation Rentals

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Headingley vacation rentals

Interior

1. The Abode family space

The Abode family space
Fort Garry
$161 nightly
The price is $189
Oct 13 - Oct 14
Total with taxes and fees
The Abode family space
A two-story house with a grey garage door, a covered driveway, and a wooden fence in the background.

2. 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.
$142 nightly
The price is $166
Oct 8 - Oct 9
Total with taxes and fees
Prairie Luxury 1 Bedrooms Home
A modern living room with a leather sofa set, a glass coffee table, and a lamp.

3. 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.
$108 nightly
The price is $126
Oct 8 - Oct 9
Total with taxes and fees
Canada Life Centre° Osborne Location
A marble table with various items including a clear glass, a white vase, a gold decorative piece, and a striped mug.

4. 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.
$84 nightly
The price is $98
Oct 14 - Oct 15
Total with taxes and fees
One-bedroom guest suite with private entry
A residential driveway with a circular brick pattern leading to a garage.

5. Golden Eagle, Basement Suite

Golden Eagle, Basement Suite
Winnipeg
9.0 out of 10, Wonderful, (17 reviews)
"Nice place liked to stay"
Canada
Simran K.
$119 nightly
The price is $139
Oct 7 - Oct 8
Total with taxes and fees
Golden Eagle, Basement Suite
A modern living room with a sectional sofa, a coffee table, a TV mounted on the wall, and a fireplace.

6. 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.
$99 nightly
The price is $116
Oct 8 - Oct 9
Total with taxes and fees
Separate Entrance Basement Suite
A wooden staircase with a modern design, leading to a dark-colored landing area.

7. 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, (2 reviews)
"Full privacy, had a peaceful stay. I highly recommend if anyone is looking for a quiet peaceful stay."
Canada
Vijaya Shree
$85 nightly
The price is $99
Nov 2 - Nov 3
Total with taxes and fees
The Peaceful Lower Loft Where Comfort Meets Quiet Escape.
A laundry room with a washer, dryer, and a standing fan.

8. The Cozy Corner Home

The Cozy Corner Home
2.0 star property
East Kildonan
$97 nightly
The price is $101
Oct 12 - Oct 13
Total with taxes and fees
The Cozy Corner Home
A dining area with a round table, chairs, and a vase of flowers.

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

Stormwater Haven: Peaceful, Stylish and comfortable space in South Winnipeg.
Fort Garry
9.2 out of 10, Wonderful, (7 reviews)
"Overall, it was a decent unit. Central enough to all the places I needed to visit. My only complaint was that it was way too cold in the unit (despite the scorching heat outside) that I had to occasionally turn on the heating which kept leading to a power outage in the unit."
Canada
Kester
$93 nightly
The price is $108
Oct 8 - Oct 9
Total with taxes and fees
Stormwater Haven: Peaceful, Stylish and comfortable space in South Winnipeg.
A modern living room with a flat-screen TV on a white entertainment unit, two grey armchairs, a patterned rug, and a small kitchen area with a microwave.

10. 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.
$95 nightly
The price is $112
Oct 8 - Oct 9
Total with taxes and fees
Duniques unique home Fully furnished 2 bedroom basement suite
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, (95 reviews)
"Lovely stay - very spacious, secure and clean! Would recommend"
Canada
Alyssa
$133 nightly
The price is $156
Oct 15 - Oct 16
Total with taxes and fees
FREE PARKING NY Style Condo in Exchange District
A staircase with dark wooden steps leading up to a landing.

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

Home away from home! Entire basement suite with privacy and driveway parking!
Fort Garry
10.0 out of 10, Exceptional, (3 reviews)
"very clean, lovely space. loved staying for our anniversary "
Canada
Rayna
$100 nightly
The price is $117
Oct 8 - Oct 9
Total with taxes and fees
Home away from home! Entire basement suite with privacy and driveway parking!
A modern hallway with a wardrobe, a kitchen area with a refrigerator, and a seating area with a sofa.

13. 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
$105 nightly
The price is $123
Oct 10 - Oct 11
Total with taxes and fees
Peaceful and spacious one bed and rec-room for short or long stay
A modern conference room with a glass table, black chairs, a large flat-screen TV, and a decorative plant.

14. Welcoming Private 2 Bedroom Suite

Welcoming Private 2 Bedroom Suite
Fort Garry
9.6 out of 10, Exceptional, (17 reviews)
"Clean area, nice peaceful area."
Canada
Vince
$108 nightly
The price is $126
Oct 8 - Oct 9
Total with taxes and fees
Welcoming Private 2 Bedroom Suite
A living room with a black sofa, a glass coffee table, a potted plant, a flat-screen TV, and a wall-mounted clock.

15. 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.
$85 nightly
The price is $99
Oct 8 - Oct 9
Total with taxes and fees
Cozy Haven 1-bedroom suite close to centre of Winnipeg
A building exterior with a textured facade, a door, and a mailbox.

16. 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.
$104 nightly
The price is $122
Oct 8 - Oct 9
Total with taxes and fees
Private Cozy 1 Bedroom Basement Suite
A living room with a flat-screen TV, a sofa, a dining table, and a plant.

17. 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.
$136 nightly
The price is $160
Oct 10 - Oct 11
Total with taxes and fees
HOME AWAY FROM HOME
Pool

18. The Wooden Nest | Your Comfy Relaxing Escape

The Wooden Nest | Your Comfy Relaxing Escape
King Edward
9.6 out of 10, Exceptional, (18 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.
$220 nightly
The price is $247
Oct 7 - Oct 8
Total with taxes and fees
The Wooden Nest | Your Comfy Relaxing Escape
A covered patio area with a wooden deck, a white lounge chair, a table, and a hanging flower basket.

19. 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
$102 nightly
The price is $124
Oct 8 - Oct 9
Total with taxes and fees
Maryland Homestay - Downtown Apartment #1
A bedroom with a bed, a painting of swans, and a door leading to a bathroom.

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

Cozy 2BR Suite • Private Entry • Free Parking• self check-in
Peguis
$114 nightly
The price is $133
Oct 9 - Oct 10
Total with taxes and fees
Cozy 2BR Suite • Private Entry • Free Parking• self check-in
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

Canad Inns Destination Centre Fort Garry

Canad Inns Destination Centre Fort Garry

8/10 Good
"Rooms were ground floor and near altos restaurants."
AGNES 2-night trip
Posted less than an hour ago
Canad Inns Destination Centre Fort Garry

Find out more about Headingley

Everything you need to know about Headingley vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Headingley vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Headingley vacation 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 low season months. For more hustle and bustle, you may prefer to visit Headingley in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $106 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Headingley rentals

At Expedia, we put the best Headingley vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Headingley?

Yes, you can find vacation rentals in Headingley close to Thunder Rapids Fun Park, or you can go with a secluded option if you're looking for a relaxing stay. Our travelers say Headingley has a good selection of coffeehouses. Make sure you have time to check out the hockey games and riverfront during your trip.

What are some of the best vacation rentals in Headingley?

St B. Living : This vacation 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 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 vacation rentals like in Headingley?

Vacation rentals are privately owned properties you can book for a few days or a quick weekend in Headingley. Vacation rentals offer extras like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy front desks while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for a family getaway.