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Top Holiday Rentals in Headingley

Our top choices for Headingley holiday rentals

Cheerful Tuxedo House with Hot Tub

9.6 out of 10, Exceptional, (15)
"Fantastic place. Plenty of room, comfortable beds and great neighborhood. Hot tub was a perfect way to end the day. I’d definitely stay here again next time"
The price is £411
includes taxes & fees
11 Sept - 12 Sept
Cheerful Tuxedo House with Hot Tub

Welcoming Private 2 Bedroom Suite

9.2 out of 10, Wonderful, (9)
"Fantastic property, excellent hosts! The beds were super comfy, everything we needed was accessible, and the place is in a fantastic location. Would definitely stay again, and highly recommend!"
The price is £100
includes taxes & fees
25 Aug - 26 Aug
Welcoming Private 2 Bedroom Suite

Full house in the best neighborhood of Winnipeg-Bridgwater Forest

5.6 out of 10, (5)
"What can I say…we checked in on a Friday planning to stay two nights. We brought our stuff up, ran a few errands while we gathered our thoughts and then ran back to grab all of our stuff even though it was non refundable we came to the conclusion we would not be comfortable and chose to leave. Pros: easy check in, replied promptly, nice neighborhood Cons: house is extremely lived in. Personal effects absolutely everywhere, don’t even consider going there with curious children who likely will...
The price is £105
includes taxes & fees
4 Sept - 5 Sept
Full house in the best neighborhood of Winnipeg-Bridgwater Forest

2500 sq ft 5 beds 3.5 bath New Home (2021)

9.4 out of 10, Exceptional, (23)
"A beautiful clean home, kitchen well stocked with plates cutlery etc. Ample parking. Enjoyable stay."
The price is £165
includes taxes & fees
2 Sept - 3 Sept
2500 sq ft 5 beds 3.5 bath New Home (2021)

3 floors character house

9.4 out of 10, Exceptional, (64)
"My second time here while visiting family in my hometown. We came in early May to unpresedented 3 day heatwave. My husband loved the house and the AC was adequte.cenwereadequate. "
3 floors character house

Afan Home of Joy

9.6 out of 10, Exceptional, (18)
"We enjoyed our 4-day stay, it was very clean, in a new home, quiet and spacious, and our hosts were very accomodating."
The price is £95
includes taxes & fees
24 Aug - 25 Aug
Afan Home of Joy

The Last Resort with private entrance. In Basement.

8.0 out of 10, Very good, (1)
"Nice place, nice people!"
The Last Resort with private entrance. In Basement.

Spacious 2 BR 1 BATH - NEAR DOWNTOWN

The price is £227
includes taxes & fees
20 Aug - 21 Aug
Spacious 2 BR 1 BATH - NEAR DOWNTOWN

2 Br/ 3 beds with free parking, wifi and much more

9.4 out of 10, Exceptional, (21)
"Great over all location"
2 Br/ 3 beds with free parking, wifi and much more

Suite with facilities to make you feel at home

The price is £8,407
includes taxes & fees
20 Aug - 21 Aug
Suite with facilities to make you feel at home

Romantic villa in 10 acres

The price is £991
includes taxes & fees
20 Aug - 21 Aug
Romantic villa in 10 acres

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

10.0 out of 10, Exceptional, (6)
"Great proximity to nice restaurants"
The price is £201
includes taxes & fees
20 Aug - 21 Aug
Cozy 2-Bedroom Loft in DT! Walking distance to the Forks and Canada Life Centre

NEW !! MODERN 1500 SF 2 BR 2.5 BA -ULTRA LUXURIOUS CONDO -OSBORNE VILLAGE !!

10.0 out of 10, Exceptional, (65)
"Very nice apartment. Great location and the parking garage was very nice!"
NEW !! MODERN 1500 SF 2 BR 2.5 BA -ULTRA LUXURIOUS CONDO -OSBORNE VILLAGE !!

Cozy Home away from Home in a Basement with a separate entrance

10.0 out of 10, Exceptional, (6)
"My wife and I stayed in Winnipeg for a few nights in Dec 2022. The suite was easily accessible, located in the lower level of a house in a residential neighborhood. Was refreshing to get away from 'corporate' for a bit. Bed was comfortable and everything that we needed was provided - even creamers for the coffee. We didn't use the TV, but apparently it has several thousand channels so you can surf to your heart's content. The host, Christiana, was very attentive and made sure we had all that we...
The price is £80
includes taxes & fees
16 Sept - 17 Sept
Cozy Home away from Home in a Basement with a separate entrance

🌎Modern 3 bedroom home w/street park’n close to ✈️

10.0 out of 10, Exceptional, (3)
"This property is beautiful. The owner is top hostess she went above and beyond for us. Will definitely being staying here again"
The price is £401
includes taxes & fees
8 Sept - 9 Sept
🌎Modern 3 bedroom home w/street park’n close to ✈️

Maryland Homestay - Downtown Apartment

The price is £102
includes taxes & fees
8 Sept - 9 Sept
Maryland Homestay - Downtown Apartment

18th floor 2 bed 2 bath overlooking downtown

8.4 out of 10, Very good, (8)
"One large shade missing, one smaller one, broken bedding cabinet, toilet paper stuck in holes of bathroom where rack might have been, lights in bathroom are poor at best and vanity lights not working, unhappy fire inspectors checking the place out, thermostat batteries corroded beyond belief. "
18th floor 2 bed 2 bath overlooking downtown

Kelvista's suite

9.8 out of 10, Exceptional, (7)
"A comfortable and affordable place to stay! The host is great with communication and the suite is lovely!"
The price is £108
includes taxes & fees
8 Sept - 9 Sept
Kelvista's suite

Luxury 2 bed 2 bath across jets arena 16th floor with amazing view

8.0 out of 10, Very good, (36)
"Would stay again "
Luxury 2 bed 2 bath across jets arena 16th floor with amazing view

Charming 2-bedroom apartment in wonderful Devonshire area of Winnipeg with WiFi

9.0 out of 10, Wonderful, (2)
"Everything was labelled and easy to find. The place was super clean and minimalist :)"
The price is £94
includes taxes & fees
28 Aug - 29 Aug
Charming 2-bedroom apartment in wonderful Devonshire area of Winnipeg with WiFi
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

Frequently asked questions

Can I find a holiday rental in Headingley?

Yes, there are holiday rentals in Headingley close to Thunder Rapids Fun Park, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Headingley has a good selection of coffee shops. Make sure you have time to check out the hockey games and riverfront during your trip.

What are some of the best holiday rentals that Headingley has to offer?

Full house in the best neighborhood of Winnipeg-Bridgwater Forest: This holiday home rental outside of Headingley offers a fireplace, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

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 holiday rentals like in Headingley?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Headingley. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from public hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for families.