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
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Headingley vacation rentals

Interior

Cheerful Tuxedo House with Hot Tub

Cheerful Tuxedo House with Hot Tub
Tuxedo
9.8 out of 10, Exceptional, (45 reviews)
"Our stay was great and hosts were wonderful. "
Canada
sharla m.
$607 nightly
The price is $713
Jul 9 - Jul 10
Total with taxes and fees
Cheerful Tuxedo House with Hot Tub
Exterior detail

Kelvista's suite

Kelvista's suite
St. Vital
9.6 out of 10, Exceptional, (14 reviews)
"Me and my family had a great stay. The host was always there when needed. Very Cozy."
Canada
Lr
$118 nightly
The price is $138
Aug 4 - Aug 5
Total with taxes and fees
Kelvista's suite
Exterior detail

Cozy Basement Suite in Winnipeg

Cozy Basement Suite in Winnipeg
St. Vital
8.0 out of 10, Very Good, (2 reviews)
"Great host, great amenities "
United States
Alyce M.
$118 nightly
The price is $139
Jul 19 - Jul 20
Total with taxes and fees
Cozy Basement Suite in Winnipeg
Smart TV

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.
$94 nightly
The price is $110
Jul 16 - Jul 17
Total with taxes and fees
Duniques unique home Fully furnished 2 bedroom basement suite
Smart TV

HOME AWAY FROM HOME

HOME AWAY FROM HOME
Fort Garry
10.0 out of 10, Exceptional, (3 reviews)
"This apartment was perfect for the two of us! Nice, clean and the bed was incredibly comfortable! Easy check in and check out! "
Canada
Tania
$132 nightly
The price is $155
Aug 6 - Aug 7
Total with taxes and fees
HOME AWAY FROM HOME
Interior

The Abode family space

The Abode family space
Fort Garry
$161 nightly
The price is $189
Jul 16 - Jul 17
Total with taxes and fees
The Abode family space
Exterior

Furnished basement with seperate entrance ,living room,washroom and kitchenette

Furnished basement with seperate entrance ,living room,washroom and kitchenette
Transcona
$85 nightly
The price is $100
Jul 16 - Jul 17
Total with taxes and fees
Furnished basement with seperate entrance ,living room,washroom and kitchenette
Fridge, microwave, oven, stovetop

*New & Modern Home | Free Parking | 5 mins Downtown*

*New & Modern Home | Free Parking | 5 mins Downtown*
Norwood East
9.8 out of 10, Exceptional, (13 reviews)
"Wonderful and comfortable accommodations. And conveniently located to downtown activities as advertised. Quiet community. "
United States
Travis W.
$308 nightly
The price is $345
Jul 26 - Jul 27
Total with taxes and fees
*New & Modern Home | Free Parking | 5 mins Downtown*
Exterior detail

Cozy 1 bedroom Apartment

Cozy 1 bedroom Apartment
East Kildonan
9.4 out of 10, Exceptional, (3 reviews)
"Quiet and safe residential area, not far from shops."
United States
Mahamoudou B.
$107 nightly
The price is $125
Jul 11 - Jul 12
Total with taxes and fees
Cozy 1 bedroom Apartment
Pool

*Cozy & Spacious | Free Parking | 15 min Downtown*

*Cozy & Spacious | Free Parking | 15 min Downtown*
St. Vital
9.0 out of 10, Wonderful, (7 reviews)
"The great place to stay, very convenient, super clean and cozy. Feels like home. Would recommend this property 100%"
United States
Mykhailo S.
$273 nightly
The price is $306
Jul 28 - Jul 29
Total with taxes and fees
*Cozy & Spacious | Free Parking | 15 min Downtown*
Exterior detail

Modern, Cozy & Stylishly Furnished Suite | Private Entrance

Modern, Cozy & Stylishly Furnished Suite | Private Entrance
St. Vital
$113 nightly
The price is $133
Jul 10 - Jul 11
Total with taxes and fees
Modern, Cozy & Stylishly Furnished Suite | Private Entrance
Private kitchen

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, (1 review)
"Was unable to stay due to family emergency but the host was very understanding to return my payment because someone else wanted to stay there at the same time. A very happy outcome for all."
United States
Jo Ann T.
$104 nightly
The price is $167
Jul 16 - Jul 17
Total with taxes and fees
Cozy two-bedroom retreat in the heart of St. Boniface,
Exterior detail

Cozy 1 bedroom basement suite with private entrance from the side of the house

Cozy 1 bedroom basement suite with private entrance from the side of the house
Winnipeg
10.0 out of 10, Exceptional, (1 review)
$94 nightly
The price is $110
Jul 27 - Jul 28
Total with taxes and fees
Cozy 1 bedroom basement suite with private entrance from the side of the house
Living area

Velvet&Rose|Elegant Private 2BR Suite|Free Parking|Wi-Fi

Velvet&Rose|Elegant Private 2BR Suite|Free Parking|Wi-Fi
Transcona
$101 nightly
The price is $118
Jul 20 - Jul 21
Total with taxes and fees
Velvet&Rose|Elegant Private 2BR Suite|Free Parking|Wi-Fi
Smart TV, fireplace

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
Jul 20 - Jul 21
Total with taxes and fees
Separate Entrance Basement Suite
TV

Cozy Winnipeg Retreat

Cozy Winnipeg Retreat
Peguis
10.0 out of 10, Exceptional, (1 review)
"Basement of a house. Super clean, quiet people that live above, good price :)"
Canada
Jaymee
$111 nightly
The price is $130
Jul 14 - Jul 15
Total with taxes and fees
Cozy Winnipeg Retreat
Interior

Cozy Nest - 1 Bedroom

Cozy Nest - 1 Bedroom
St. Vital
$111 nightly
The price is $130
Jul 20 - Jul 21
Total with taxes and fees
Cozy Nest - 1 Bedroom
Exterior detail

Charming Bedroom in Bonavista

Charming Bedroom in Bonavista
St. Vital
8.0 out of 10, Very Good, (2 reviews)
"The place was very clean and very very new. There was still the stickers from original packaging on the TV and some appliances. Apparently the laundry room is locked and you are only given access if you stay 4 nights. This was not made clear when booking. I was also under the impression that I was renting the whole house and that the second bedroom could be rented if I chose so. However, j found out that there would be a person I didn't know who rented out the slate bedroom. Luckily, the owner...
United States
Wesley R.
$111 nightly
The price is $130
Jul 19 - Jul 20
Total with taxes and fees
Charming Bedroom in Bonavista
Property grounds

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.
$101 nightly
The price is $118
Jul 26 - Jul 27
Total with taxes and fees
STYLISH 2-BEDROOM BASEMENT SUITE.PRIVATE ENTRANCE& PARKING. NEAR U OF M 4GUESTS!
Exterior

Amazing 2-Bedroom Basement Suite

Amazing 2-Bedroom Basement Suite
St. Vital
$144 nightly
The price is $169
Jul 16 - Jul 17
Total with taxes and fees
Amazing 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

Super 8 by Wyndham Winnipeg East MB

Super 8 by Wyndham Winnipeg East MB

8/10 Good
"Hot tub was not in use and pool was murky and the floor muddy , people never took there outside shoes off. Stayed 2 nights no maid service. Monday morning extremely busy and couldn’t keep up with breakfast items. Beds very comfortable and room was very clean. Will stay again just leave my bathing suit at home"
Kathryn 2-night trip
Posted 6 hours ago
Super 8 by Wyndham Winnipeg East MB

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 $108 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?

Brilliant 4-bedroom house with AC in Winnipeg: This vacation home rental outside of Headingley offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a stovetop, and a microwave, 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 Softball Complex and John Blumberg Golf Course 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.