Headingley Holiday Rentals

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Holiday Rentals in Headingley

Our top choices for Headingley holiday rentals

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

10.0 out of 10, Exceptional, (7)
"Great proximity to nice restaurants"
The price is NZ$457
includes taxes & fees
28 Sept - 29 Sept
Cozy 2-Bedroom Loft in DT! Walking distance to the Forks and Canada Life Centre

Morning glory cottage

9.0 out of 10, Wonderful, (37)
"Good place "
The price is NZ$148
includes taxes & fees
25 Sept - 26 Sept
Morning glory cottage

2 bed downtown sleeps 5 across jets arena king bed

8.8 out of 10, Excellent, (26)
"Exactly what we needed for a group of four"
2 bed downtown sleeps 5 across jets arena king bed

FREE PARKING NY Style Condo in Exchange District

10.0 out of 10, Exceptional, (65)
"Beautiful condo, tastefully decorated and very comfortable "
The price is NZ$260
includes taxes & fees
1 Oct - 2 Oct
FREE PARKING NY Style Condo in Exchange District

Downtown luxury 1 bedroom sleeps 3 wifi and laundry

8.4 out of 10, Very good, (9)
"Overall it was good."
Downtown luxury 1 bedroom sleeps 3 wifi and laundry

Maryland Homestay - Downtown Apartment #1

8.0 out of 10, Very good, (3)
"Great communication with host. Addressed any questions promptly. Good location and rental."
The price is NZ$209
includes taxes & fees
29 Sept - 30 Sept
Maryland Homestay - Downtown Apartment #1

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 NZ$236
includes taxes & fees
25 Sept - 26 Sept
Full house in the best neighborhood of Winnipeg-Bridgwater Forest

Home Away from Home! Family-sized vacations, group getaways, business trips,

9.4 out of 10, Exceptional, (6)
"It was supplied all essential needs. It was in an excellent neighborhood. The place was clean and welcoming. Felt like home as we were evacuated from our placement in Flin Flon, Manitoba."
Home Away from Home! Family-sized vacations, group getaways, business trips,

Fully Furnished Basement Unit – Private Entrance Included

8.8 out of 10, Excellent, (3)
"Well maintained and very clean."
The price is NZ$177
includes taxes & fees
25 Sept - 26 Sept
Fully Furnished Basement Unit – Private Entrance Included

Prairie Luxury 2 Bedrooms Home

9.2 out of 10, Wonderful, (5)
"The property is beautiful and my children had access to the basketball net. However, we were only given 1 facecloth as a hand towel for 4 days in the bathroom even when I asked for a couple of extra towels lol "
The price is NZ$349
includes taxes & fees
23 Oct - 24 Oct
Prairie Luxury 2 Bedrooms Home

Cozy Modern Suite - Peaceful Stay & Hwy Access

10.0 out of 10, Exceptional, (2)
"Clean and quiet quaint oasis that we stayed overnight while attending a Celebration of Life. Host was very helpful. Easy to get to from the airport. Exactly what we needed. No hassles and a restful sleep. "
The price is NZ$160
includes taxes & fees
25 Sept - 26 Sept
Cozy Modern Suite - Peaceful Stay & Hwy Access

St B. Living

9.4 out of 10, Exceptional, (12)
"Had a nice one night stay here. Thank you!"
The price is NZ$224
includes taxes & fees
28 Sept - 29 Sept
St B. Living

Private Cozy 1 Bedroom Basement Suite

10.0 out of 10, Exceptional, (3)
"Nice clean place to stay"
The price is NZ$214
includes taxes & fees
28 Sept - 29 Sept
Private Cozy 1 Bedroom Basement Suite

🌎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 NZ$909
includes taxes & fees
1 Oct - 2 Oct
🌎Modern 3 bedroom home w/street park’n close to ✈️

Afan Home of Joy

9.6 out of 10, Exceptional, (19)
"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 NZ$212
includes taxes & fees
29 Sept - 30 Sept
Afan Home of Joy

Kelvista's suite

9.8 out of 10, Exceptional, (9)
"A comfortable and affordable place to stay! The host is great with communication and the suite is lovely!"
The price is NZ$221
includes taxes & fees
30 Sept - 1 Oct
Kelvista's suite

Suite with facilities to make you feel at home

The price is NZ$19,346
includes taxes & fees
25 Sept - 26 Sept
Suite with facilities to make you feel at home

2 LUXURY BEDROOM IN BASEMENT FOR 4 PEOPLE !!!

9.2 out of 10, Wonderful, (7)
"Just loved our stay there .. all was clean, neat and matches the app descriptions. "
The price is NZ$206
includes taxes & fees
10 Oct - 11 Oct
2 LUXURY BEDROOM IN BASEMENT FOR 4 PEOPLE !!!

Maryland Homestay - Downtown Apartment

The price is NZ$229
includes taxes & fees
29 Sept - 30 Sept
Maryland Homestay - Downtown Apartment

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

9.2 out of 10, Wonderful, (23)
"Next door to a lovely coffee shop and beer garden, a short walk to Tall Grass Prairie bakery and centrally located in Winnipeg to easily get to all the places we needed to go to. "
2 Br/ 3 beds with free parking, wifi and much more
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

Find out more about Headingley

Find out more about Headingley

Everything you need to know about Headingley holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Headingley holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Headingley holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Headingley holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Headingley. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Headingley holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Headingley holiday rentals we have selected for you start as low as NZ$148 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Headingley rentals

At Expedia, we put the best Headingley holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Headingley rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Headingley holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Headingley. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Home Away from Home! Family-sized vacations, group getaways, business trips, : This holiday home rental outside of Headingley offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that 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 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.