A rural landscape with a field of tall grass, two grain silos, and a wooden barn under a colorful sky.

Headingley Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Headingley vacation rentals

Smart TV

The Snug Spot,Retreat offers a warm and inviting escape for travelers.

The Snug Spot,Retreat offers a warm and inviting escape for travelers.
St. Vital
10.0 out of 10, Exceptional, (10 reviews)
"Lovely and clean place."
Canada
Lidya
The price is ￥11,249
￥17,586 total
includes taxes & fees
Jul 27 - Jul 28
The Snug Spot,Retreat offers a warm and inviting escape for travelers.
Property grounds

Luxury: Home Away from Home with Private Entrance

Luxury: Home Away from Home with Private Entrance
Transcona
8.8 out of 10, Excellent, (5 reviews)
"This was a great stay! Very clean and easy process, host was very quick to answer questions 👍"
Canada
Owen
The price is ￥5,711
￥18,446 total
includes taxes & fees
Jul 19 - Jul 20
Luxury: Home Away from Home with Private Entrance
Exterior detail

Kelvista's suite

Kelvista's suite
St. Vital
9.6 out of 10, Exceptional, (14 reviews)
"Me and my family had a great stay. The host was always there when needed. Very Cozy."
Canada
Lr
The price is ￥8,567
￥22,501 total
includes taxes & fees
Aug 7 - Aug 8
Kelvista's suite
TV

Cozy Winnipeg Retreat

Cozy Winnipeg Retreat
Peguis
10.0 out of 10, Exceptional, (1 review)
"Basement of a house. Super clean, quiet people that live above, good price :)"
Canada
Jaymee
The price is ￥10,692
￥21,636 total
includes taxes & fees
Jul 16 - Jul 17
Cozy Winnipeg Retreat
Smart TV

Exquisite 1-bedroom basement in the quiet neighbourhood of Bonavista, Winnipeg

Exquisite 1-bedroom basement in the quiet neighbourhood of Bonavista, Winnipeg
St. Vital
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 ￥8,567
￥17,772 total
includes taxes & fees
Jul 22 - Jul 23
Exquisite 1-bedroom basement in the quiet neighbourhood of Bonavista, Winnipeg
Exterior

Elegant 1-Bedroom Basement Suite

Elegant 1-Bedroom Basement Suite
St. Vital
8.8 out of 10, Excellent, (6 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 ￥7,960
￥18,448 total
includes taxes & fees
Aug 13 - Aug 14
Elegant 1-Bedroom Basement 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.
The price is ￥12,851
￥18,786 total
includes taxes & fees
Jul 16 - Jul 17
Separate Entrance Basement Suite
Interior

Serenity meets class: Entire Basement Suite in Winnipeg

Serenity meets class: Entire Basement Suite in Winnipeg
St. Vital
9.6 out of 10, Exceptional, (28 reviews)
"Had a great stay"
Canada
Sarah U.
The price is ￥7,539
￥15,879 total
includes taxes & fees
Aug 5 - Aug 6
Serenity meets class: Entire Basement Suite in Winnipeg
Exterior

Furnished basement with seperate entrance ,living room,washroom and kitchenette

Furnished basement with seperate entrance ,living room,washroom and kitchenette
Transcona
The price is ￥7,196
￥16,149 total
includes taxes & fees
Jul 16 - Jul 17
Furnished basement with seperate entrance ,living room,washroom and kitchenette
Smart TV

Fully Furnished Basement Unit – Private Entrance Included

Fully Furnished Basement Unit – Private Entrance Included
St. Vital
9.0 out of 10, Wonderful, (12 reviews)
"Great clean spot"
United States
Dustin
The price is ￥10,852
￥16,421 total
includes taxes & fees
Jul 15 - Jul 16
Fully Furnished Basement Unit – Private Entrance Included
Private kitchen

Cozy two-bedroom retreat in the heart of St. Boniface,

Cozy two-bedroom retreat in the heart of St. Boniface,
Central St. Boniface
10.0 out of 10, Exceptional, (1 review)
"Was unable to stay due to family emergency but the host was very understanding to return my payment because someone else wanted to stay there at the same time. A very happy outcome for all."
United States
Jo Ann T.
The price is ￥10,330
￥27,240 total
includes taxes & fees
Jul 27 - Jul 28
Cozy two-bedroom retreat in the heart of St. Boniface,
Interior

Entire Guest Suite/Separate Entrance/Free Parking in Winnipeg

Entire Guest Suite/Separate Entrance/Free Parking in Winnipeg
Transcona
9.8 out of 10, Exceptional, (10 reviews)
"This property was an amazing experience and i really enjoyed my stay with my partner and will definitely rebook this place again."
Canada
Priscilla N.
The price is ￥8,590
￥21,852 total
includes taxes & fees
Jul 29 - Jul 30
Entire Guest Suite/Separate Entrance/Free Parking in Winnipeg
Interior

Private Suite | Prairie Pointe & Near UofM

Private Suite | Prairie Pointe & Near UofM
Fort Garry
9.6 out of 10, Exceptional, (5 reviews)
"Great little suite, host was very pleasant and accommodating. Quiet, comfortable, would stay here again 100%."
Canada
Melissa D.
The price is ￥7,710
￥15,407 total
includes taxes & fees
Jul 15 - Jul 16
Private Suite | Prairie Pointe & Near UofM
Exterior

Golden Eagle, Basement Suite

Golden Eagle, Basement Suite
Winnipeg
9.6 out of 10, Exceptional, (12 reviews)
"Nice place liked to stay"
Canada
Simran K.
The price is ￥10,623
￥24,932 total
includes taxes & fees
Jul 29 - Jul 30
Golden Eagle, Basement Suite
Property grounds

STYLISH 2-BEDROOM BASEMENT SUITE.PRIVATE ENTRANCE& PARKING. NEAR U OF M 4GUESTS!

STYLISH 2-BEDROOM BASEMENT SUITE.PRIVATE ENTRANCE& PARKING. NEAR U OF M 4GUESTS!
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.
The price is ￥9,709
￥19,123 total
includes taxes & fees
Jul 29 - Jul 30
STYLISH 2-BEDROOM BASEMENT SUITE.PRIVATE ENTRANCE& PARKING. NEAR U OF M 4GUESTS!
Interior

One-bedroom guest suite with private entry

One-bedroom guest suite with private entry
East Kildonan
9.8 out of 10, Exceptional, (9 reviews)
"Clean, quiet, safe community, felt like home."
Canada
Sheri
The price is ￥8,178
￥15,990 total
includes taxes & fees
Jul 28 - Jul 29
One-bedroom guest suite with private entry
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
The price is ￥17,134
￥30,736 total
includes taxes & fees
Jul 16 - Jul 17
Northside Comfort! Pet Friendly Budget Rental close to HSC and The Forks!!!
Exterior

Morning glory cottage

Morning glory cottage
Peguis
8.6 out of 10, Excellent, (40 reviews)
"Very friendly host great location"
Canada
Caleb
The price is ￥7,461
￥14,463 total
includes taxes & fees
Jul 25 - Jul 26
Morning glory cottage
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.
The price is ￥10,281
￥22,501 total
includes taxes & fees
Jul 19 - Jul 20
Cozy Basement Suite in Winnipeg
Interior

Cheerful Tuxedo House with Hot Tub

Cheerful Tuxedo House with Hot Tub
Tuxedo
9.8 out of 10, Exceptional, (46 reviews)
"Our stay was great and hosts were wonderful. "
Canada
sharla m.
The price is ￥44,926
￥114,006 total
includes taxes & fees
Jul 15 - Jul 16
Cheerful Tuxedo House with Hot Tub
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

Super 8 by Wyndham Winnipeg East MB

Super 8 by Wyndham Winnipeg East MB

10/10 Excellent
"Clean and convenient. Nice pool"
Evan 1-night trip
Posted 6 hours ago
Super 8 by Wyndham Winnipeg East MB

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:

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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?

Brilliant 4-bedroom house with AC in Winnipeg: This vacation home rental outside of Headingley offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a stovetop, and a microwave, 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 Softball Complex 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.