Headingley Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Apr 3 - Apr 5
In two months
May 15 - May 17
In three months
Jun 12 - Jun 14
In four months
Jul 10 - Jul 12

Our top choices for Headingley vacation rentals

Smart TV, fireplace

Vacation Home in Fort Garry

Separate Entrance Basement Suite
8.0 out of 10, Very Good, (11 reviews)
"Very good services."
Canada
Alabi A.
The price is ￥11,423
￥17,035 total
includes taxes & fees
Mar 17 - Mar 18
Separate Entrance Basement Suite
Interior

Vacation Home in East Kildonan

One-bedroom guest suite with private entry
9.8 out of 10, Exceptional, (7 reviews)
"Nice and well take care of place, host was very helpful and kind, highly recommended, for my first time in Winnipeg was easy access, convenient and close to the area I needed to be. "
Canada
Gabriela V.
The price is ￥7,190
￥14,783 total
includes taxes & fees
Mar 17 - Mar 18
One-bedroom guest suite with private entry
Dining

Vacation Home in Fort Garry

Welcoming Private 2 Bedroom Suite
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.
The price is ￥8,733
￥20,740 total
includes taxes & fees
Mar 17 - Mar 18
Welcoming Private 2 Bedroom Suite
Exterior detail

Vacation Home in St. Vital

Kelvista's suite
9.6 out of 10, Exceptional, (11 reviews)
"This property was amazing would love to stay here again "
Canada
Oluwatimilehin
The price is ￥7,860
￥21,774 total
includes taxes & fees
Mar 21 - Mar 22
Kelvista's suite
Exterior detail

Vacation Home in Fort Garry

Private Cozy 1 Bedroom Basement Suite
9.2 out of 10, Wonderful, (5 reviews)
"Nice clean place to stay"
United States
Thomas B.
The price is ￥10,479
￥20,050 total
includes taxes & fees
Mar 17 - Mar 18
Private Cozy 1 Bedroom Basement Suite
Exterior

Apartment in St. Vital

Elegant 1-Bedroom Basement Suite
9.6 out of 10, Exceptional, (4 reviews)
"Well maintained clean property. The owner of the home was very accomodating and kind. Great location. Felt like home during our stay! Will definitely come back."
Canada
Sameh
The price is ￥7,336
￥17,709 total
includes taxes & fees
Mar 17 - Mar 18
Elegant 1-Bedroom Basement Suite
Interior

Vacation Home in St. Vital

Serenity meets class: Entire Basement Suite in Winnipeg
9.2 out of 10, Wonderful, (14 reviews)
"We had a great stay. The host was prompt to answer questions and the space was perfect for a weekend getaway. "
Canada
Lonna
The price is ￥6,812
￥15,024 total
includes taxes & fees
Mar 19 - Mar 20
Serenity meets class: Entire Basement Suite in Winnipeg
Exterior

Vacation Home in Fort Garry

Prairie Luxury 1 Bedrooms Home
10.0 out of 10, Exceptional, (1 review)
The price is ￥7,336
￥27,352 total
includes taxes & fees
Mar 17 - Mar 18
Prairie Luxury 1 Bedrooms Home
2 bedrooms, iron/ironing board, WiFi, bed sheets

Vacation Home in Fort Garry

Mary's Luxury Suite
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.
The price is ￥7,336
￥21,153 total
includes taxes & fees
Mar 17 - Mar 18
Mary's Luxury Suite
Property grounds

Apartment in Fort Garry

2 LUXURY BEDROOM IN BASEMENT FOR 4 PEOPLE !!!
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.
The price is ￥8,908
￥18,193 total
includes taxes & fees
Mar 17 - Mar 18
2 LUXURY BEDROOM IN BASEMENT FOR 4 PEOPLE !!!
Living area

Vacation Home in Winnipeg

Cozy Haven 1-bedroom suite close to centre of Winnipeg
10.0 out of 10, Exceptional, (2 reviews)
"Would definitely stay here again if I’m ever in Winnipeg! "
Canada
Ashton P.
The price is ￥8,908
￥16,126 total
includes taxes & fees
Mar 17 - Mar 18
Cozy Haven 1-bedroom suite close to centre of Winnipeg
Pool

Vacation Home in Winnipeg

*1min Riverview Health 7min Downtown Free Parking
9.0 out of 10, Wonderful, (10 reviews)
"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.
The price is ￥14,304
￥32,713 total
includes taxes & fees
Mar 17 - Mar 18
*1min Riverview Health 7min Downtown Free Parking
Smart TV, fireplace

Vacation Home in St. Vital

Private Basement Apartment with separate entrance
10.0 out of 10, Exceptional, (1 review)
"Perfect for a 1 night stay. Just passing through. "
Canada
Norman
The price is ￥12,808
￥20,601 total
includes taxes & fees
Mar 17 - Mar 18
Private Basement Apartment with separate entrance
Smart TV, fireplace

Vacation Home in St. Vital

Cozy Home away from Home in a Basement with a separate entrance
9.2 out of 10, Wonderful, (10 reviews)
"Check in was easy, place was nice."
Canada
Blair J.
The price is ￥12,808
￥20,050 total
includes taxes & fees
Mar 17 - Mar 18
Cozy Home away from Home in a Basement with a separate entrance
Interior

Vacation Home in Tuxedo

Cheerful Tuxedo House with Hot Tub
9.8 out of 10, Exceptional, (40 reviews)
"We totally enjoyed our stay!"
Canada
peter S.
The price is ￥46,110
￥110,715 total
includes taxes & fees
Mar 23 - Mar 24
Cheerful Tuxedo House with Hot Tub
Fridge, microwave, oven, stovetop

Vacation Home in Norwood East

*New & Modern Home | Free Parking | 5 mins Downtown*
9.8 out of 10, Exceptional, (7 reviews)
"Great place"
Canada
Blaine
The price is ￥14,577
￥33,149 total
includes taxes & fees
Mar 17 - Mar 18
*New & Modern Home | Free Parking | 5 mins Downtown*
Interior

Vacation Home in Fort Garry

Restful Haven
The price is ￥10,479
￥20,050 total
includes taxes & fees
Mar 17 - Mar 18
Restful Haven
TV, fireplace

Vacation Home in Lord Roberts

Basement Suite on Osborne
9.0 out of 10, Wonderful, (7 reviews)
"When we come back to Winnipeg we would definitely like to stay at this accommodation again. Safe, friendly neighborhood. Great tacos at BMC close by. Safeway close by."
United States
Cynthia B.
The price is ￥10,479
￥15,918 total
includes taxes & fees
Mar 17 - Mar 18
Basement Suite on Osborne
Exterior

Apartment in Winnipeg

Golden Eagle, Basement Suite
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
The price is ￥8,908
￥17,503 total
includes taxes & fees
Mar 21 - Mar 22
Golden Eagle, Basement Suite
Smart TV

Apartment in St. Vital

Exquisite 1-bedroom basement in the quiet neighbourhood of Bonavista, Winnipeg
10.0 out of 10, Exceptional, (2 reviews)
"Overall enjoyed my stay the place was well kept and completely hosted myself and two friends for the weekend. In a great neighborhood felt safe and a beautiful park walking distance away. I recommend it’s comfortable and affordable."
Canada
Hana S.
The price is ￥8,151
￥17,296 total
includes taxes & fees
Mar 17 - Mar 18
Exquisite 1-bedroom basement in the quiet neighbourhood of Bonavista, Winnipeg
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Headingley Hotel Reviews

Canad Inns Destination Centre Fort Garry

Canad Inns Destination Centre Fort Garry

6/10 Okay
"Front desk staff inefficient and difficult to understand. Room amenities not replaced during stay. Used soap in the bathroom. No cups provided."
Richard 2-night trip
Posted 1 hour ago
Canad Inns Destination Centre Fort Garry

Find out more about Headingley

Search for holiday rentals in Headingley on Expedia! You can easily find your home rentals, villas, holiday apartments in Headingley using one of the methods below:

  • View our selection of featured holiday rentals in Headingley
  • Use the map to find apartments and other holiday homes in the Headingley neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Headingley while they last

Look no further and take a look at our great range of rental properties in Headingley!

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?

Luxurious House in a Desired Location, King Bed: This vacation home rental outside of Headingley offers a fireplace, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. 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. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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.