Headingley Vacation Rentals

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Check prices for these dates

In two weeks
Apr 10 - Apr 12
In two months
May 22 - May 24
In three months
Jun 19 - Jun 21
In four months
Jul 17 - Jul 19

Our top choices for Headingley vacation rentals

Exterior detail

Kelvista's suite

Kelvista's suite
St. Vital
9.6 out of 10, Exceptional, (11 reviews)
"This property was amazing would love to stay here again "
Canada
Oluwatimilehin
$123 nightly
The price is $145
Apr 10 - Apr 11
Total with taxes and fees
Kelvista's suite
Interior

Cheerful Tuxedo House with Hot Tub

Cheerful Tuxedo House with Hot Tub
Tuxedo
9.8 out of 10, Exceptional, (40 reviews)
"We totally enjoyed our stay!"
Canada
peter S.
$577 nightly
The price is $679
Apr 2 - Apr 3
Total with taxes and fees
Cheerful Tuxedo House with Hot Tub
Smart TV, fireplace

Separate Entrance Basement Suite

Separate Entrance Basement Suite
Fort Garry
8.0 out of 10, Very Good, (11 reviews)
"Very good services."
Canada
Alabi A.
$101 nightly
The price is $118
Mar 30 - Mar 31
Total with taxes and fees
Separate Entrance Basement 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.
$99 nightly
The price is $116
Mar 30 - Mar 31
Total with taxes and fees
Cozy Basement Suite in Winnipeg
Exterior

Prairie Luxury 2 Bedrooms Home

Prairie Luxury 2 Bedrooms Home
Fort Garry
9.4 out of 10, Exceptional, (6 reviews)
"Great place. Easy, convenient location. Clean and spacious."
Canada
Randy H.
$169 nightly
The price is $198
Mar 30 - Mar 31
Total with taxes and fees
Prairie Luxury 2 Bedrooms Home
Exterior

Golden Eagle, Basement Suite

Golden Eagle, Basement Suite
Winnipeg
9.8 out of 10, Exceptional, (6 reviews)
"The host was really.nice and respectful, he is on top for respond to my needs concerning any supplies for my stay,, I just only want he be lenient a little with the guess for small details ( s.all hair in the bathroom/ carpet/ bed) after that I give 5 stars, and highly recommended. "
United States
Lesly
$90 nightly
The price is $105
Mar 29 - Mar 30
Total with taxes and fees
Golden Eagle, Basement Suite
Interior

Modern 5 bedroom Lake view home in Prairie Pointe, winnipeg

Modern 5 bedroom Lake view home in Prairie Pointe, winnipeg
Fort Garry
10.0 out of 10, Exceptional, (1 review)
"The place was spotless and the host was absolutely very courteous. "
Canada
Lilly
$427 nightly
The price is $502
Mar 30 - Mar 31
Total with taxes and fees
Modern 5 bedroom Lake view home in Prairie Pointe, winnipeg
Dining

Welcoming Private 2 Bedroom Suite

Welcoming Private 2 Bedroom Suite
Fort Garry
9.2 out of 10, Wonderful, (12 reviews)
"The place is clean and the host was a call away and gave us their info in case we need help. "
Canada
Mila D.
$110 nightly
The price is $129
Apr 1 - Apr 2
Total with taxes and fees
Welcoming Private 2 Bedroom Suite
Pool

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, (31 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.
Modern house in trendy location in South Winnipeg-Bridgwater Area
Interior

🌎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 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.
$454 nightly
The price is $534
Mar 29 - Mar 30
Total with taxes and fees
🌎Modern 3 bedroom home w/street park’n close to ✈️
Interior

Serenity meets class: Entire Basement Suite in Winnipeg

Serenity meets class: Entire Basement Suite in Winnipeg
St. Vital
9.2 out of 10, Wonderful, (15 reviews)
"We had a great stay. The host was prompt to answer questions and the space was perfect for a weekend getaway. "
Canada
Lonna
$80 nightly
The price is $94
Apr 3 - Apr 4
Total with taxes and fees
Serenity meets class: Entire Basement Suite in Winnipeg
Smart TV, fireplace

Cozy Home away from Home in a Basement with a separate entrance

Cozy Home away from Home in a Basement with a separate entrance
St. Vital
9.2 out of 10, Wonderful, (10 reviews)
"Check in was easy, place was nice."
Canada
Blair J.
$107 nightly
The price is $125
Mar 30 - Mar 31
Total with taxes and fees
Cozy Home away from Home in a Basement with a separate entrance
Exterior detail

Private Cozy 1 Bedroom Basement Suite

Private Cozy 1 Bedroom Basement Suite
Fort Garry
9.2 out of 10, Wonderful, (5 reviews)
"Nice clean place to stay"
United States
Thomas B.
$107 nightly
The price is $125
Mar 30 - Mar 31
Total with taxes and fees
Private Cozy 1 Bedroom Basement Suite
Property grounds

Luxury: Home Away from Home with Private Entrance

Luxury: Home Away from Home with Private Entrance
Transcona
8.6 out of 10, Excellent, (4 reviews)
"Nice suite, clean and relatively new. some defects pointed out to the owner and very receptive of comments."
Canada
Bill H.
$99 nightly
The price is $116
Apr 2 - Apr 3
Total with taxes and fees
Luxury: Home Away from Home with Private Entrance
Pool

*1min Riverview Health 7min Downtown Free Parking

*1min Riverview Health 7min Downtown Free Parking
Winnipeg
9.0 out of 10, Wonderful, (10 reviews)
"Very clean. Bedrooms all on lower level- it worked out well when you have people getting up at different times in the morning. 2 1/2 bathrooms, ideal for when everyone’s trying to get ready and leave at the same time. I would stay again "
Canada
Susan G.
*1min Riverview Health 7min Downtown Free Parking
Property grounds

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 reviews)
"We had a great stay! Hosts were communicative and we have nothing but good things to say about property itself."
Canada
Aidan M.
$97 nightly
The price is $113
Mar 30 - Mar 31
Total with taxes and fees
2 LUXURY BEDROOM IN BASEMENT FOR 4 PEOPLE !!!
Smart TV, fireplace

Private Basement Apartment with separate entrance

Private Basement Apartment with separate entrance
St. Vital
10.0 out of 10, Exceptional, (1 review)
"Perfect for a 1 night stay. Just passing through. "
Canada
Norman
$101 nightly
The price is $119
Mar 29 - Mar 30
Total with taxes and fees
Private Basement Apartment with separate entrance
Smart TV, fireplace

Magnificent Stylish Escape

Magnificent Stylish Escape
Fort Garry
$1,011 nightly
The price is $1,188
Mar 30 - Mar 31
Total with taxes and fees
Magnificent Stylish Escape
2 bedrooms, iron/ironing board, WiFi, bed sheets

Mary's Luxury Suite

Mary's Luxury Suite
Fort Garry
9.0 out of 10, Wonderful, (2 reviews)
"It was great and wanted to apologize for the in and out, my son vapes so he kelp going in and out. I wasn’t sure which door you were referring to, to leave open. Had a great sleep! And Saskatchewan won so we were happy! Thank you! "
Canada
Patricia S.
$112 nightly
The price is $132
Apr 7 - Apr 8
Total with taxes and fees
Mary's Luxury 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

Birchwood Inn, BW Premier Collection

Birchwood Inn, BW Premier Collection

10/10 Excellent
"Clean room Friendly staff"
Brenda 2-night trip
Posted 1 hour ago
Birchwood Inn, BW Premier Collection

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 $94 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?

3 floors character house: This vacation home rental outside of Headingley is located in the city center and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

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.