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

Headingley Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Headingley vacation rentals

Interior

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.
$336 nightly
The price is $395
Aug 25 - Aug 26
Total with taxes and fees
The Guest Expertise – Where Elegance Meets Comfort in a 5BR Luxury Retreat
Interior

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.
$878 nightly
The price is $1,032
Sep 1 - Sep 2
Total with taxes and fees
Luxury Tuxedo Family Home with Hot Tub
Interior

3. 6 BEDROOM MAGNIFICENT STYLISH ESCAPE

6 BEDROOM MAGNIFICENT STYLISH ESCAPE
Fort Garry
$1,411 nightly
The price is $1,658
Aug 23 - Aug 24
Total with taxes and fees
6 BEDROOM MAGNIFICENT STYLISH ESCAPE
Interior

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.
$461 nightly
The price is $541
Aug 23 - Aug 24
Total with taxes and fees
🌎Modern 3 bedroom home w/street park’n close to ✈️
Pool

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.
$386 nightly
The price is $454
Sep 16 - Sep 17
Total with taxes and fees
Luxurious House in a Desired Location, King Bed
Pool

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
$231 nightly
The price is $272
Aug 27 - Aug 28
Total with taxes and fees
Spacious new 3 Bedroom, sleeps 10, King Bed, 8min to YWG
Living area

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.
$140 nightly
The price is $165
Aug 24 - Aug 25
Total with taxes and fees
HOME AWAY FROM HOME
Living area

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.
$155 nightly
The price is $182
Sep 1 - Sep 2
Total with taxes and fees
Northside Comfort! Pet Friendly Budget Rental close to HSC and The Forks!!!
Pool

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.
$348 nightly
The price is $409
Sep 1 - Sep 2
Total with taxes and fees
Modern house in trendy location in South Winnipeg-Bridgwater Area
Pool

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.
$232 nightly
The price is $260
Sep 8 - Sep 9
Total with taxes and fees
The Wooden Nest | Your Comfy Relaxing Escape
Private kitchen

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.
$155 nightly
The price is $182
Aug 23 - Aug 24
Total with taxes and fees
Northside Comfort 2 !!! Pet Friendly Budget Rental Close to HSC and The Forks
Living area

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.
$102 nightly
The price is $120
Sep 2 - Sep 3
Total with taxes and fees
Separate Entrance Basement Suite
Room

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.
$231 nightly
The price is $272
Aug 24 - Aug 25
Total with taxes and fees
Beautiful Home In A Prime Location
Exterior

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.
$159 nightly
The price is $187
Sep 1 - Sep 2
Total with taxes and fees
Prairie Luxury 2 Bedrooms Home
Interior

15. Manhattan Suite

Manhattan Suite
Fort Garry
$111 nightly
The price is $130
Aug 24 - Aug 25
Total with taxes and fees
Manhattan Suite
Interior

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
$174 nightly
The price is $205
Aug 23 - Aug 24
Total with taxes and fees
Retraite Saint Boniface/St. Boniface Retreat
Living area

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.
$224 nightly
The price is $263
Aug 24 - Aug 25
Total with taxes and fees
Modern 2 Bedroom Home In A Prime Location
Room

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.
$144 nightly
The price is $169
Aug 24 - Aug 25
Total with taxes and fees
Mary's Luxury Suite
Private kitchen

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.
$108 nightly
The price is $126
Aug 26 - Aug 27
Total with taxes and fees
Cozy 2-Bedroom Home in St-Boniface – 5 Min Walk to Food, Fuel & More
Living area

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.
$97 nightly
The price is $113
Aug 23 - Aug 24
Total with taxes and fees
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

Canad Inns Destination Centre Transcona

Canad Inns Destination Centre Transcona

8/10 Good
"The hotel itself was nice enough, though it is old and could really use an upgrade. Our room had a very strong musty smell, either from the air conditioner or there had been a flood of water in the room. The front desk was nice enough to comp us for breakfast due to the inconvenience. The housekeeping room was just down the hall from us and there were always maids carts blocking the path to our room day and night. There should be a time where the hallway is free to walk with out obstacles."
Robert 1-night trip
Posted 2 hours ago
Canad Inns Destination Centre Transcona

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 $104 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?

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