Headingley Vacation Rentals

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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

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
$121 nightly
The price is $142
May 25 - May 26
Total with taxes and fees
Kelvista's suite
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, (11 reviews)
"Amazing location right in Saint Boniface! Clean and new house with great amenities. "
United States
Dawson M.
$181 nightly
The price is $203
May 25 - May 26
Total with taxes and fees
*New & Modern Home | Free Parking | 5 mins Downtown*
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.
$97 nightly
The price is $114
May 25 - May 26
Total with taxes and fees
Separate Entrance Basement Suite
Exterior

Amazing 2 bedroom basement with separate entrance

Amazing 2 bedroom basement with separate entrance
St. Vital
10.0 out of 10, Exceptional, (1 review)
"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.
$145 nightly
The price is $170
May 29 - May 30
Total with taxes and fees
Amazing 2 bedroom basement with separate entrance
Exterior detail

Cozy 1 bedroom Apartment

Cozy 1 bedroom Apartment
East Kildonan
10.0 out of 10, Exceptional, (2 reviews)
"Quiet and safe residential area, not far from shops."
United States
Mahamoudou B.
$110 nightly
The price is $129
May 25 - May 26
Total with taxes and fees
Cozy 1 bedroom Apartment
Interior

One-bedroom guest suite with private entry

One-bedroom guest suite with private entry
East Kildonan
9.8 out of 10, Exceptional, (7 reviews)
"Clean, quiet, safe community, felt like home."
Canada
Sheri
$86 nightly
The price is $101
May 25 - May 26
Total with taxes and fees
One-bedroom guest suite with private entry
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
9.4 out of 10, Exceptional, (6 reviews)
"Nice and attractive place … host has good communication "
United States
Benson-Ifere E.
$107 nightly
The price is $125
May 25 - May 26
Total with taxes and fees
Cozy 2-Bedroom Home in St-Boniface – 5 Min Walk to Food, Fuel & More
Interior

Serenity meets class: Entire Basement Suite in Winnipeg

Serenity meets class: Entire Basement Suite in Winnipeg
St. Vital
9.4 out of 10, Exceptional, (22 reviews)
"We had a great stay. The host was prompt to answer questions and the space was perfect for a weekend getaway. "
Canada
Lonna
$81 nightly
The price is $94
Jun 8 - Jun 9
Total with taxes and fees
Serenity meets class: Entire Basement Suite in Winnipeg
Private kitchen

Stylish & Spacious | Minutes from Downtown

Stylish & Spacious | Minutes from Downtown
Central St. Boniface
10.0 out of 10, Exceptional, (5 reviews)
"Well stocked, spacious, and central. Glad I stayed here. "
Canada
Dale K.
$160 nightly
The price is $180
May 25 - May 26
Total with taxes and fees
Stylish & Spacious | Minutes from Downtown
Exterior

Prairie Luxury 1 Bedrooms Home

Prairie Luxury 1 Bedrooms Home
Fort Garry
9.6 out of 10, Exceptional, (5 reviews)
"Enjoyed my 3 night stay very much here! The property was exceptionally clean and modern! It was also very easy to communicate with the owner regarding check in and check out rules! Great and safe location."
Canada
Emma
$145 nightly
The price is $171
May 25 - May 26
Total with taxes and fees
Prairie Luxury 1 Bedrooms Home
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.
$122 nightly
The price is $143
May 25 - May 26
Total with taxes and fees
Cozy Basement Suite in Winnipeg
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.
$136 nightly
The price is $160
May 25 - May 26
Total with taxes and fees
Mary's Luxury Suite
Fridge, microwave, oven, stovetop

2 Private Bedrooms in Winnipeg1

2 Private Bedrooms in Winnipeg1
East Kildonan
9.0 out of 10, Wonderful, (13 reviews)
"Clean. Great Location. "
Canada
Lorna
$165 nightly
The price is $194
May 25 - May 26
Total with taxes and fees
2 Private Bedrooms in Winnipeg1
1 bedroom, WiFi, bed sheets

Cozy 1-bedroom with King size bed

Cozy 1-bedroom with King size bed
Winnipeg
$95 nightly
The price is $111
May 29 - May 30
Total with taxes and fees
Cozy 1-bedroom with King size bed
Interior

Cheerful Tuxedo House with Hot Tub

Cheerful Tuxedo House with Hot Tub
Tuxedo
9.8 out of 10, Exceptional, (43 reviews)
"Host was very welcoming, location was great."
Canada
Okudero O.
$693 nightly
The price is $814
May 31 - Jun 1
Total with taxes and fees
Cheerful Tuxedo House with Hot Tub
Private kitchen

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

Velvet&Rose|Elegant Private 2BR Suite|Free Parking|Wi-Fi
Transcona
$96 nightly
The price is $113
May 25 - May 26
Total with taxes and fees
Velvet&Rose|Elegant Private 2BR Suite|Free Parking|Wi-Fi
Interior

The Abode family space

The Abode family space
Fort Garry
$165 nightly
The price is $194
May 30 - May 31
Total with taxes and fees
The Abode family space
Pool

Amazing 4 Bedrooms Entire Home in Winnipeg with Free parking, Wi-fi and more

Amazing 4 Bedrooms Entire Home in Winnipeg with Free parking, Wi-fi and more
East Kildonan
9.6 out of 10, Exceptional, (4 reviews)
"This was a perfect location for the things we needed to do Winnipeg."
Canada
Christopher H.
$224 nightly
The price is $263
May 25 - May 26
Total with taxes and fees
Amazing 4 Bedrooms Entire Home in Winnipeg with Free parking, Wi-fi and more
Smart TV

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, (1 review)
"I liked most things with this property. We were a bit worried about the location as it was in a less than desirable neighbourhood. Having said that, the manager was wonderful and always willing to help. The neighbours across the road were friendly and helpful. There are security cameras and lots of light so coming home late was not an issue. All in all, I believe we got a fair and good deal."
Canada
Brenda
$154 nightly
The price is $181
May 27 - May 28
Total with taxes and fees
Northside Comfort! Pet Friendly Budget Rental close to HSC and The Forks!!!
Fridge, microwave, oven, stovetop

*Refresh | Central & Trendy | 5 min to downtown*

*Refresh | Central & Trendy | 5 min to downtown*
Central St. Boniface
9.6 out of 10, Exceptional, (8 reviews)
"Very nice place to stay ! "
Canada
Michelle
$184 nightly
The price is $206
May 25 - May 26
Total with taxes and fees
*Refresh | Central & Trendy | 5 min to downtown*
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

Inn At The Forks

Inn At The Forks

4/10 Poor
"Positive: -beautiful spacious suite, comfortable chairs and living room furniture, hot water and tub were great, fantastic location -male staff at front desk on morning of May 23, 2026, offered loaner umbrella Needs Improvement: -only one side of the bed had a hub to plug in cell phone, etc.; housekeeping staff said they had nothing else to help, & instead showed up with a spare block and cord -phone in bedroom did not work; informed front desk and housekeeping, was ignored -both room key cards did not open the safe; only the last one to lock it could open it -not much vegetarian food on the SMITH restaurant menu -front desk staff on evening of May 21, 2026 was useless: female never heard of Johnston Terminal & had no clue what was right beside the hotel to provide any information, male staff was busy speaking Punjabi on his phone -SMITH restaurant staff: Asian female with long straight hair on evening of May 21, 2026, brought wrong food to us, and then was oblivious about an item I left behind, and instead said my take out container had been discarded; I went in to look and found my item right where I left it; she smiles but is as helpful as a pinecone -May 22 evening, asked for more coffee and cream to be sent to our room while we went out for supper; 2.5 hours later, not done; we had to ask again -May 22, 2026, found someone's cut fingernail on the desk while I had a work meeting -May 22, 2026, found a corn kernel on the living room floor near sofa -suite needs more light"
Brian 2-night trip
Posted 4 hours ago
Inn At The Forks

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?

Welcome to cozy suites in a great neighborhood With lot of amenities .: This vacation home rental outside of Headingley is equipped with a patio, air-conditioning, and a Smart TV to help you feel comfortable during your stay.

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.