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
24 Jul - 26 Jul
In two months
4 Sep - 6 Sep
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Headingley vacation rentals

Living area

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

Velvet&Rose|Elegant Private 2BR Suite|Free Parking|Wi-Fi
Transcona
The price is AED 259
AED 434 total
includes taxes & fees
13 Jul - 14 Jul
Velvet&Rose|Elegant Private 2BR Suite|Free Parking|Wi-Fi
Smart TV

Spacious & cozy family/group-sized home with backyard, deck & Gazebo!

Spacious & cozy family/group-sized home with backyard, deck & Gazebo!
Transcona
Spacious & cozy family/group-sized home with backyard, deck & Gazebo!
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 AED 130
AED 419 total
includes taxes & fees
20 Jul - 21 Jul
Luxury: Home Away from Home with Private Entrance
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 AED 195
AED 495 total
includes taxes & fees
24 Jul - 25 Jul
Entire Guest Suite/Separate Entrance/Free Parking 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 AED 163
AED 366 total
includes taxes & fees
22 Jul - 23 Jul
Furnished basement with seperate entrance ,living room,washroom and kitchenette
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
9.0 out of 10, Wonderful, (6 reviews)
The price is AED 275
AED 483 total
includes taxes & fees
29 Jul - 30 Jul
Royal Oak - 2-bedroom (King & Queen bed), Living Area, Kitchen and Full bathroom
Shower, towels, soap, toilet paper

Cozy 1-Bedroom Private Basement Suite in Winnipeg. Separate Entrance.

Cozy 1-Bedroom Private Basement Suite in Winnipeg. Separate Entrance.
Peguis
10.0 out of 10, Exceptional, (1 review)
"A very clean, quiet, cozy, and comfortable stay. Easy to find. Thank you."
United States
Robert L.
The price is AED 285
AED 465 total
includes taxes & fees
3 Aug - 4 Aug
Cozy 1-Bedroom Private Basement Suite in Winnipeg. Separate Entrance.
Interior

Blissful 2 bedroom basement in Winnipeg with Wifi, AC

Blissful 2 bedroom basement in Winnipeg with Wifi, AC
Peguis
8.0 out of 10, Very Good, (2 reviews)
"Easy to check-in. Fast wifi. Large space. It is dark as there are few windows and a table/chairs would be nice. The TV, couch, and chair are weirdly oriented, but it is a very good value for a 2 bedroom"
United States
William M.
The price is AED 181
AED 479 total
includes taxes & fees
3 Aug - 4 Aug
Blissful 2 bedroom basement in Winnipeg with Wifi, AC
Smart TV

Family suit near costco with free parking and wifi

Family suit near costco with free parking and wifi
Peguis
The price is AED 189
AED 457 total
includes taxes & fees
20 Jul - 21 Jul
Family suit near costco with free parking and wifi
Living area

Cozy 3-Bedroom Basement Suite with Private Entrance

Cozy 3-Bedroom Basement Suite with Private Entrance
Transcona
8.0 out of 10, Very Good, (1 review)
"The unit itself was very nice. Clean and well stocked for needs. Was advertised as a three bedroom but only two of them were accessible. Not sure why one bedroom was locked. Overall a nice place but one issue was the people upstairs must have had company and were extremely loud. A couple mornings there was a lot of stomping around at 6am. So the sound proofing between upstairs and downstairs isn’t great. Even so, I would still consider staying here again. Host was very quick in responding to...
Canada
Kyle M.
The price is AED 233
AED 695 total
includes taxes & fees
22 Jul - 23 Jul
Cozy 3-Bedroom Basement Suite with Private Entrance
Exterior detail

Afan Home of Joy (Private Entrance)

Afan Home of Joy (Private Entrance)
Peguis
9.4 out of 10, Exceptional, (26 reviews)
"Thanks for the stay, it was a good place to rest and reset in the evening after busy days outside."
Canada
Graham J.
The price is AED 228
AED 473 total
includes taxes & fees
16 Jul - 17 Jul
Afan Home of Joy (Private Entrance)
Smart TV

Cozy 1BR Suite + Sitting Room | Quick Access to Regent East

Cozy 1BR Suite + Sitting Room | Quick Access to Regent East
Transcona
8.0 out of 10, Very Good, (1 review)
"The place was clean, host was very nice. There was some small things that didn’t go as planned. One was that there is a family living upstairs but they were quiet for the most part, they were loud sometimes but not too bad. There was a kid that came downstairs and opened the bedroom door while we were sleeping but the host took care of it quickly. They also only put three forks when there were four of us staying and other small things like that. Overall very nice place and would definitely stay...
United States
Maddix
The price is AED 233
AED 449 total
includes taxes & fees
22 Jul - 23 Jul
Cozy 1BR Suite + Sitting Room | Quick Access to Regent East
Interior

Cozy Nest - 1 Bedroom

Cozy Nest - 1 Bedroom
St. Vital
The price is AED 207
AED 480 total
includes taxes & fees
20 Jul - 21 Jul
Cozy Nest - 1 Bedroom
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
10.0 out of 10, Exceptional, (1 review)
" Exceptional Stay – A True Home Away From HomeI had an outstanding stay at this beautiful B&B and would highly recommend it to anyone traveling for business or pleasure.The apartment was exceptionally clean, well-maintained, and thoughtfully equipped with everything I could possibly need. From the moment I arrived, it felt more like a home than a rental. Rachel has clearly put a great deal of thought into ensuring her guests are comfortable, providing not only all the necessities but also many...
United States
marta s.
The price is AED 243
AED 552 total
includes taxes & fees
4 Aug - 5 Aug
Warm, Inviting Basement Suite • Quiet Stay in a Safe, Upscale Area
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 AED 235
AED 558 total
includes taxes & fees
27 Jul - 28 Jul
Golden Eagle, Basement Suite
Exterior

Morning glory cottage

Morning glory cottage
Peguis
8.6 out of 10, Excellent, (40 reviews)
"Very friendly host great location"
Canada
Caleb
Morning glory cottage
Property grounds

Embassy Suites.

Embassy Suites.
Peguis
6.8 out of 10, (6 reviews)
"Had a great stay, room was clean and cozy and easy to check in."
Canada
Shastina
The price is AED 169
AED 465 total
includes taxes & fees
25 Jul - 26 Jul
Embassy Suites.
Interior

Best place to stay and enjoy your money

Best place to stay and enjoy your money
Peguis
8.4 out of 10, Very Good, (5 reviews)
"Owner was very friendly and house was well maintained "
Canada
Erik
The price is AED 156
AED 327 total
includes taxes & fees
25 Jul - 26 Jul
Best place to stay and enjoy your money
1 bedroom, WiFi, bed sheets

Cozy 1-bedroom with King size bed

Cozy 1-bedroom with King size bed
Winnipeg
2.0 out of 10, (1 review)
"The price was right. It looks ok until you started to look closer at the room. Things were not clean. The bed mattress was flat from people and smells . No top sheet. And the bed cover was dirty. The pillows smells. Did not use them. I was supposed to get a lock code and was not giving. No lock key for my room to lock up my things when I went out and was locked out two times from the house. I feel like a prisoner . No wifi was not giving a password also. And yes I asked for the door lock...
Canada
Lydia
The price is AED 151
AED 398 total
includes taxes & fees
10 Jul - 11 Jul
Cozy 1-bedroom with King size bed
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 AED 240
AED 488 total
includes taxes & fees
13 Jul - 14 Jul
Cozy Winnipeg Retreat
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
"All good, no complaints"
John 1-night trip
Posted 7 hours ago
Humphry Inn & Suites

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.