Headingley Vacation Rentals

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Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

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
The price is ￥8,629
￥22,663 total
includes taxes & fees
Jul 4 - Jul 5
Kelvista's suite
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.
The price is ￥17,833
￥84,687 total
includes taxes & fees
Jun 18 - Jun 19
🌎Modern 3 bedroom home w/street park’n close to ✈️
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.
The price is ￥20,709
￥29,468 total
includes taxes & fees
Jun 18 - Jun 19
Amazing 2 bedroom basement with separate entrance
Hair dryer, towels, soap, toilet paper

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

Velvet&Rose|Elegant Private 2BR Suite|Free Parking|Wi-Fi
Transcona
The price is ￥10,354
￥17,899 total
includes taxes & fees
Jun 17 - Jun 18
Velvet&Rose|Elegant Private 2BR Suite|Free Parking|Wi-Fi
Interior

Cheerful Tuxedo House with Hot Tub

Cheerful Tuxedo House with Hot Tub
Tuxedo
9.8 out of 10, Exceptional, (43 reviews)
"Our stay was great and hosts were wonderful. "
Canada
sharla m.
The price is ￥44,202
￥113,489 total
includes taxes & fees
Jun 9 - Jun 10
Cheerful Tuxedo House with Hot Tub
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 ￥8,652
￥21,328 total
includes taxes & fees
Jun 17 - Jun 18
Entire Guest Suite/Separate Entrance/Free Parking in Winnipeg
Interior

The Abode family space

The Abode family space
Fort Garry
The price is ￥13,806
￥30,957 total
includes taxes & fees
Jun 18 - Jun 19
The Abode family space
Interior

Cozy 2BR in Winnipeg. Near airport, food, bus, hospital. Home away from home.

Cozy 2BR in Winnipeg. Near airport, food, bus, hospital. Home away from home.
Weston
The price is ￥16,107
￥24,705 total
includes taxes & fees
Jun 18 - Jun 19
Cozy 2BR in Winnipeg. Near airport, food, bus, hospital. Home away from home.
Interior

The Guest Expertise – Where Elegance Meets Comfort in a 5BR Luxury Retreat

The Guest Expertise – Where Elegance Meets Comfort in a 5BR Luxury Retreat
Winnipeg
10.0 out of 10, Exceptional, (3 reviews)
"This property suited us well for a business meeting to the city! Very nice neighborhood "
Canada
Marilee K.
The price is ￥29,353
￥65,646 total
includes taxes & fees
Jun 21 - Jun 22
The Guest Expertise – Where Elegance Meets Comfort in a 5BR Luxury Retreat
Pool

*1min Riverview Health 7min Downtown Free Parking

*1min Riverview Health 7min Downtown Free Parking
Winnipeg
9.0 out of 10, Wonderful, (12 reviews)
"Host very helpful. Quick to respond and sort out any issues.Amenities were fantastic."
United States
osayimwense o.
The price is ￥26,652
￥47,761 total
includes taxes & fees
Jun 18 - Jun 19
*1min Riverview Health 7min Downtown Free Parking
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 ￥15,532
￥28,788 total
includes taxes & fees
Jun 18 - Jun 19
Northside Comfort! Pet Friendly Budget Rental close to HSC and The Forks!!!
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 ￥6,903
￥19,940 total
includes taxes & fees
Jul 6 - Jul 7
Furnished basement with seperate entrance ,living room,washroom and kitchenette
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, (23 reviews)
"Clean, great location and cozy space."
Canada
Varsy
The price is ￥8,173
￥16,683 total
includes taxes & fees
Jun 8 - Jun 9
Serenity meets class: Entire Basement Suite in Winnipeg
Pool

*New & Spacious | Free Parking | 7min to Downtown*

*New & Spacious | Free Parking | 7min to Downtown*
Lord Roberts
8.8 out of 10, Excellent, (13 reviews)
"Large, bright home with everything you need. Good location close to everything. "
United States
Tracy G.
*New & Spacious | Free Parking | 7min to Downtown*
Fridge, microwave, oven, stovetop

St B. Living

St B. Living
Central St. Boniface
9.6 out of 10, Exceptional, (24 reviews)
"The apartment is in a busy but fun neighborhood with easy walking access to a grocery and dollar store and restaurants. It was also a 25 minute walk to the Forks to go out. It was great to have the small parking spot. The apartment was clean and modern with all necessary amenities."
United States
Deborah
The price is ￥15,022
￥21,382 total
includes taxes & fees
Jun 7 - Jun 8
St B. Living
Dining

Stormwater Haven: Peaceful, Stylish and comfortable space in South Winnipeg.

Stormwater Haven: Peaceful, Stylish and comfortable space in South Winnipeg.
Fort Garry
The price is ￥10,354
￥21,301 total
includes taxes & fees
Jul 4 - Jul 5
Stormwater Haven: Peaceful, Stylish and comfortable space in South Winnipeg.
Interior

Royal Oak - 2-bedroom (King & Queen bed), Living Area, Kitchen and Full bathroom

Royal Oak - 2-bedroom (King & Queen bed), Living Area, Kitchen and Full bathroom
Peguis
9.6 out of 10, Exceptional, (4 reviews)
"Newer basement suite. Comfortable King bed. Nice size shower. "
United States
Ken R.
The price is ￥11,908
￥21,099 total
includes taxes & fees
Jun 17 - Jun 18
Royal Oak - 2-bedroom (King & Queen bed), Living Area, Kitchen and Full bathroom
Exterior

Warm, Inviting Basement Suite • Quiet Stay in a Safe, Upscale Area

Warm, Inviting Basement Suite • Quiet Stay in a Safe, Upscale Area
St. Vital
The price is ￥11,390
￥22,527 total
includes taxes & fees
Jun 18 - Jun 19
Warm, Inviting Basement Suite • Quiet Stay in a Safe, Upscale Area
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
Cozy Winnipeg Retreat
Interior

Cozy Nest - 1 Bedroom

Cozy Nest - 1 Bedroom
St. Vital
The price is ￥9,204
￥21,301 total
includes taxes & fees
Jun 18 - Jun 19
Cozy Nest - 1 Bedroom
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

Humphry Inn & Suites

Humphry Inn & Suites

10/10 Excellent
"Well located. Parking lot very tight!"
David 1-night trip
Posted 5 hours ago
Humphry Inn & Suites

Find out more about Headingley

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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?

Cozy Modern Basement Suite in Devonshire Winnipeg: This vacation home rental outside of Headingley has air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

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.