Headingley Vacation Rentals

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Check prices for these dates

In two weeks
Dec 5 - Dec 7
In two months
Jan 16 - Jan 18
In three months
Feb 13 - Feb 15
In four months
Mar 13 - Mar 15

Vacation Rentals in Headingley

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

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

2.0 star property
Fort Garry
$141 nightly
The price is $166
Nov 24 - Nov 25
Total with taxes and fees
Stormwater Haven: Peaceful, Stylish and comfortable space in South Winnipeg.
Interior
St. Thérèse’s Nest: Your Peaceful Retreat Minutes from the Pulse of the City

St. Thérèse’s Nest: Your Peaceful Retreat Minutes from the Pulse of the City

2.0 star property
Lord Roberts
10.0 out of 10, Exceptional, (1)
"Check in was easy. Great location. Parking on street in front of house no problem. Kitchen had the basics. Tassimo made wonderful coffee. Beds comfortable but firm. Host was exceptionally attentive and accommodating. She was a blessing."
Canada
Joanne S.
$241 nightly
The price is $284
Nov 23 - Nov 24
Total with taxes and fees
St. Thérèse’s Nest: Your Peaceful Retreat Minutes from the Pulse of the City
1 bedroom, iron/ironing board, free WiFi, bed sheets
Cozy Modern Suite - Peaceful Stay & Hwy Access

Cozy Modern Suite - Peaceful Stay & Hwy Access

Fort Garry
9.4 out of 10, Exceptional, (3)
"Clean and quiet quaint oasis that we stayed overnight while attending a Celebration of Life. Host was very helpful. Easy to get to from the airport. Exactly what we needed. No hassles and a restful sleep. "
Canada
Nadine M.
$107 nightly
The price is $126
Nov 23 - Nov 24
Total with taxes and fees
Cozy Modern Suite - Peaceful Stay & Hwy Access
Fridge, microwave, stovetop, coffee/tea maker
Amazing 2 bedroom basement with separate entrance

Amazing 2 bedroom basement with separate entrance

St. Vital
10.0 out of 10, Exceptional, (1)
"The basement apartment was very clean and in a very good location. She was very helpful when we needed something and we had a nice little vacation in Winnipeg."
Canada
Sharon W.
$131 nightly
The price is $154
Nov 23 - Nov 24
Total with taxes and fees
Amazing 2 bedroom basement with separate entrance
Exterior
Golden Eagle

Golden Eagle

Winnipeg
10.0 out of 10, Exceptional, (1)
"Very clean and as advertised. Beds were very comfortable."
Canada
Harold
$98 nightly
The price is $115
Nov 25 - Nov 26
Total with taxes and fees
Golden Eagle
Dining
2 Bed rooms|Private entrance|Free Parking|Self-Check-in into our Upscale Haven.

2 Bed rooms|Private entrance|Free Parking|Self-Check-in into our Upscale Haven.

Transcona
9.6 out of 10, Exceptional, (10)
"Good location to stay"
United States
Sarah
$107 nightly
The price is $125
Dec 6 - Dec 7
Total with taxes and fees
2 Bed rooms|Private entrance|Free Parking|Self-Check-in into our Upscale Haven.
Interior
Luxury: Home Away from Home with Private Entrance

Luxury: Home Away from Home with Private Entrance

Transcona
8.0 out of 10, Very Good, (3)
"Nice suite, clean and relatively new. some defects pointed out to the owner and very receptive of comments."
Canada
Bill H.
$98 nightly
The price is $115
Nov 29 - Nov 30
Total with taxes and fees
Luxury: Home Away from Home with Private Entrance
Private kitchen
Stylish & Spacious | Minutes from Downtown

Stylish & Spacious | Minutes from Downtown

Central St. Boniface
10.0 out of 10, Exceptional, (3)
"Well stocked, spacious, and central. Glad I stayed here. "
Canada
Dale K.
$168 nightly
The price is $188
Nov 23 - Nov 24
Total with taxes and fees
Stylish & Spacious | Minutes from Downtown
Smart TV, books
Best place to stay and enjoy your money

Best place to stay and enjoy your money

Peguis
9.6 out of 10, Exceptional, (4)
"Owner was very friendly and house was well maintained "
Canada
Erik
$72 nightly
The price is $84
Nov 23 - Nov 24
Total with taxes and fees
Best place to stay and enjoy your money
Private kitchen
Cozy 3-Bedroom Basement Suite with Private Entrance

Cozy 3-Bedroom Basement Suite with Private Entrance

2.0 star property
Transcona
$155 nightly
The price is $182
Nov 23 - Nov 24
Total with taxes and fees
Cozy 3-Bedroom Basement Suite with Private Entrance
Dining
2 LUXURY BEDROOM IN BASEMENT FOR 4 PEOPLE !!!

2 LUXURY BEDROOM IN BASEMENT FOR 4 PEOPLE !!!

Fort Garry
9.4 out of 10, Exceptional, (8)
"It was a quick trip and a nice place to stay! Bridgwater area is very interesting to navigate, but all in all it was decent place to stay"
Canada
Vanessa M.
$101 nightly
The price is $119
Nov 23 - Nov 24
Total with taxes and fees
2 LUXURY BEDROOM IN BASEMENT FOR 4 PEOPLE !!!
Fridge, microwave, stovetop, electric kettle
Private Basement Apartment with separate entrance

Private Basement Apartment with separate entrance

St. Vital
10.0 out of 10, Exceptional, (1)
"Perfect for a 1 night stay. Just passing through. "
Canada
Norman
$94 nightly
The price is $110
Nov 23 - Nov 24
Total with taxes and fees
Private Basement Apartment with separate entrance
Fridge, microwave, stovetop, coffee/tea maker
AVOCADO EXECUTIVE SUITES

AVOCADO EXECUTIVE SUITES

St. Vital
8.0 out of 10, Very Good, (3)
"The apartment was very neat, I got immediate response when I had issues. I will always recommend for family and friends. "
Canada
TITILAYO O.
$121 nightly
The price is $142
Nov 29 - Nov 30
Total with taxes and fees
AVOCADO EXECUTIVE SUITES
TV, fireplace
Restful Haven

Restful Haven

Fort Garry
$98 nightly
The price is $115
Nov 23 - Nov 24
Total with taxes and fees
Restful Haven
Exterior
🌎Modern 3 bedroom home w/street park’n close to ✈️

🌎Modern 3 bedroom home w/street park’n close to ✈️

Weston
10.0 out of 10, Exceptional, (3)
"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.
$450 nightly
The price is $528
Nov 23 - Nov 24
Total with taxes and fees
🌎Modern 3 bedroom home w/street park’n close to ✈️
Fridge, microwave, stovetop, coffee/tea maker
Kelvista's suite

Kelvista's suite

St. Vital
9.4 out of 10, Exceptional, (10)
"A comfortable and affordable place to stay! The host is great with communication and the suite is lovely!"
Canada
Laura
$112 nightly
The price is $131
Nov 24 - Nov 25
Total with taxes and fees
Kelvista's suite
Pool
*1min Riverview Health 7min Downtown Free Parking

*1min Riverview Health 7min Downtown Free Parking

Winnipeg
9.0 out of 10, Wonderful, (6)
"The home was as advertised. The beds were really good. The kitchen should be better stocked for a home. The carpet in the living room should be replaced. We enjoyed our stay."
Canada
adina w.
$171 nightly
The price is $191
Nov 24 - Nov 25
Total with taxes and fees
*1min Riverview Health 7min Downtown Free Parking
Exterior detail
Private Cozy 1 Bedroom Basement Suite

Private Cozy 1 Bedroom Basement Suite

Fort Garry
9.2 out of 10, Wonderful, (5)
"Amenities. Very bright and a floor lamp and small end table would be good. No where to cook a meal. Microwave doesn’t cut the mustard! Wide open to upstairs. Concept is good, but these things would be great. We did like it. "
Canada
Ray
$105 nightly
The price is $123
Nov 24 - Nov 25
Total with taxes and fees
Private Cozy 1 Bedroom Basement Suite
Fridge, microwave, oven, stovetop
Modern, Prime Location & Comfort

Modern, Prime Location & Comfort

Ebby-Wentworth
10.0 out of 10, Exceptional, (2)
"We stayed here because we were in town for an event at the Pan Am pool. It is a beautiful place with all immunities we needed. Beds were very comfortable and the place was spotless. It’s clear that it’s been through a total renovation very recently. Parking was easy and a relatively short walk (10 minutes at our pace) to grocery, Canadian Tire and a few restaurants. Also easy to get to other parts of town like the airport and Fork district, both within about 15 minutes. Only one recommendation,...
Canada
Simon H.
$150 nightly
The price is $168
Nov 30 - Dec 1
Total with taxes and fees
Modern, Prime Location & Comfort
Private kitchen
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
10.0 out of 10, Exceptional, (3)
"Nice and attractive place … host has good communication "
United States
Benson-Ifere E.
$118 nightly
The price is $138
Nov 30 - Dec 1
Total with taxes and fees
Cozy 2-Bedroom Home in St-Boniface – 5 Min Walk to Food, Fuel & More
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

10/10 Excellent
"Amazing place to stay"
Brittany 4-night trip
Posted 2 days 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 $84 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?

Afan Home of Joy: This vacation home rental outside of Headingley has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

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, Beaudry Provincial Park 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.