Headingley Vacation Rentals

Check prices for these dates

In two weeks
Apr 24 - Apr 26
In two months
Jun 5 - Jun 7
In three months
Jul 3 - Jul 5
In four months
Jul 31 - Aug 2

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 $144
Apr 23 - Apr 24
Total with taxes and fees
Kelvista's suite
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.
$101 nightly
The price is $118
Apr 27 - Apr 28
Total with taxes and fees
Separate Entrance 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
$419 nightly
The price is $494
Apr 27 - Apr 28
Total with taxes and fees
Modern 5 bedroom Lake view home in Prairie Pointe, winnipeg
Smart TV, fireplace

Magnificent Stylish Escape

Magnificent Stylish Escape
Fort Garry
$1,012 nightly
The price is $1,190
Apr 9 - Apr 10
Total with taxes and fees
Magnificent Stylish Escape
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.
$628 nightly
The price is $737
Apr 29 - Apr 30
Total with taxes and fees
Cheerful Tuxedo House with Hot Tub
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
Apr 9 - Apr 10
Total with taxes and fees
Private Cozy 1 Bedroom Basement Suite
Pool

Luxurious House in a Desired Location, King Bed

Luxurious House in a Desired Location, King Bed
Fort Garry
10.0 out of 10, Exceptional, (46 reviews)
"Everything about this property was fantastic! Very clean, large property and extremely comfortable. We'll absolutely stay here again. Fantastic hosts!"
Canada
Tom A.
$365 nightly
The price is $429
Apr 12 - Apr 13
Total with taxes and fees
Luxurious House in a Desired Location, King Bed
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.
$168 nightly
The price is $197
Apr 11 - Apr 12
Total with taxes and fees
Prairie Luxury 2 Bedrooms Home
Interior

Retraite Saint Boniface/St. Boniface Retreat

Retraite Saint Boniface/St. Boniface Retreat
Central St. Boniface
9.8 out of 10, Exceptional, (7 reviews)
"Great neighborhood and great place to stay "
Canada
jenn
$171 nightly
The price is $201
Apr 24 - Apr 25
Total with taxes and fees
Retraite Saint Boniface/St. Boniface Retreat
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
$79 nightly
The price is $92
Apr 23 - Apr 24
Total with taxes and fees
One-bedroom guest suite with private entry
Dining

Welcoming Private 2 Bedroom Suite

Welcoming Private 2 Bedroom Suite
Fort Garry
9.4 out of 10, Exceptional, (13 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 24 - Apr 25
Total with taxes and fees
Welcoming Private 2 Bedroom Suite
Exterior detail

Afan Home of Joy

Afan Home of Joy
Peguis
9.6 out of 10, Exceptional, (24 reviews)
"This is a wonderful space and we enjoyed our time staying here. Will would definitely stay again!"
Canada
Desiree R.
$112 nightly
The price is $131
Apr 23 - Apr 24
Total with taxes and fees
Afan Home of Joy
Interior

Cozy 2-Bedroom Loft in DT! Walking distance to the Forks and Canada Life Centre

Cozy 2-Bedroom Loft in DT! Walking distance to the Forks and Canada Life Centre
Exchange District
9.2 out of 10, Wonderful, (14 reviews)
"Very responsive host and great location! 2 minute walk to the Royal Manitoba Museum and great restaurants nearby! "
Canada
Raequel G.
$224 nightly
The price is $264
Apr 9 - Apr 10
Total with taxes and fees
Cozy 2-Bedroom Loft in DT! Walking distance to the Forks and Canada Life Centre
Living area

Cozy Haven 1-bedroom suite close to centre of Winnipeg

Cozy Haven 1-bedroom suite close to centre of Winnipeg
Winnipeg
10.0 out of 10, Exceptional, (2 reviews)
"Would definitely stay here again if I’m ever in Winnipeg! "
Canada
Ashton P.
$86 nightly
The price is $101
Apr 9 - Apr 10
Total with taxes and fees
Cozy Haven 1-bedroom suite close to centre of Winnipeg
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.
$106 nightly
The price is $125
Apr 24 - Apr 25
Total with taxes and fees
Cozy 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.
$106 nightly
The price is $125
Apr 24 - Apr 25
Total with taxes and fees
Cozy Home away from Home in a Basement with a separate entrance
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.
$100 nightly
The price is $117
Apr 12 - Apr 13
Total with taxes and fees
Luxury: Home Away from Home with Private Entrance
Smart TV

Fully Furnished Basement Unit – Private Entrance Included

Fully Furnished Basement Unit – Private Entrance Included
St. Vital
8.8 out of 10, Excellent, (9 reviews)
"Nice place "
Canada
hanad m.
$88 nightly
The price is $103
Apr 24 - Apr 25
Total with taxes and fees
Fully Furnished Basement Unit – Private Entrance Included
Exterior

Golden Eagle, Basement Suite

Golden Eagle, Basement Suite
Winnipeg
9.8 out of 10, Exceptional, (6 reviews)
"Very clean and as advertised. Beds were very comfortable."
Canada
Harold
$90 nightly
The price is $105
Apr 23 - Apr 24
Total with taxes and fees
Golden Eagle, Basement Suite
Interior

The Abode family space

The Abode family space
Fort Garry
$164 nightly
The price is $193
Apr 24 - Apr 25
Total with taxes and fees
The Abode family space
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

Mere Hotel

Mere Hotel

10/10 Excellent
"Great hotel and location for what we needed "
Maria 1-night trip
Posted 2 hours ago
Mere Hotel

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?

*New & Modern Home | Free Parking | 5 mins Downtown*: This vacation home rental outside of Headingley is equipped with a selection of books, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, 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 Golf Course and Beaudry Provincial Park 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.