Holiday Rentals in Headingley

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Holiday Rentals in Headingley

Peaceful Tyson Trail Retreat .

2.0 star property
Transcona
The price is €103
includes taxes & fees
30 Nov - 1 Dec
Peaceful Tyson Trail Retreat .

Golden Eagle

Winnipeg
10.0 out of 10, Exceptional, (1)
"Very clean and as advertised. Beds were very comfortable."
Canada
Harold
The price is €106
includes taxes & fees
15 Dec - 16 Dec
Golden Eagle

St. Thérèse’s Nest: Your Peaceful Retreat Minutes from the Pulse of the City

2.0 star property
Lord Roberts
10.0 out of 10, Exceptional, (1)
"Check in was easy. Great location. Parking on street in front of house no problem. Kitchen had the basics. Tassimo made wonderful coffee. Beds comfortable but firm. Host was exceptionally attentive and accommodating. She was a blessing."
Canada
Joanne S.
The price is €250
includes taxes & fees
30 Nov - 1 Dec
St. Thérèse’s Nest: Your Peaceful Retreat Minutes from the Pulse of the City

Amazing 2 bedroom basement with separate entrance

St. Vital
10.0 out of 10, Exceptional, (1)
"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 €143
includes taxes & fees
28 Dec - 29 Dec
Amazing 2 bedroom basement with separate entrance

Cozy Modern Suite - Peaceful Stay & Hwy Access

Fort Garry
9.6 out of 10, Exceptional, (4)
"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. "
Canada
Nadine M.
The price is €113
includes taxes & fees
30 Nov - 1 Dec
Cozy Modern Suite - Peaceful Stay & Hwy Access

Luxury: Home Away from Home with Private Entrance

Transcona
8.6 out of 10, Excellent, (4)
"Nice suite, clean and relatively new. some defects pointed out to the owner and very receptive of comments."
Canada
Bill H.
The price is €103
includes taxes & fees
7 Dec - 8 Dec
Luxury: Home Away from Home with Private Entrance

Stylish & Spacious | Minutes from Downtown

Central St. Boniface
10.0 out of 10, Exceptional, (3)
"Well stocked, spacious, and central. Glad I stayed here. "
Canada
Dale K.
The price is €167
includes taxes & fees
1 Dec - 2 Dec
Stylish & Spacious | Minutes from Downtown

AVOCADO EXECUTIVE SUITES

St. Vital
8.0 out of 10, Very good, (3)
"The apartment was very neat, I got immediate response when I had issues. I will always recommend for family and friends. "
Canada
TITILAYO O.
The price is €128
includes taxes & fees
30 Nov - 1 Dec
AVOCADO EXECUTIVE SUITES

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

2.0 star property
Fort Garry
The price is €154
includes taxes & fees
10 Dec - 11 Dec
Stormwater Haven: Peaceful, Stylish and comfortable space in South Winnipeg.

Lakeview walkout suite - private Entrance

2.0 star property
Fort Garry
The price is €95
includes taxes & fees
30 Nov - 1 Dec
Lakeview walkout suite - private Entrance

2 Bed rooms|Private entrance|Free Parking|Self-Check-in into our Upscale Haven.

Transcona
9.6 out of 10, Exceptional, (10)
"Good location to stay"
United States
Sarah
The price is €104
includes taxes & fees
3 Dec - 4 Dec
2 Bed rooms|Private entrance|Free Parking|Self-Check-in into our Upscale Haven.

Cozy 2-Bedroom Home in St-Boniface – 5 Min Walk to Food, Fuel & More

Central St. Boniface
10.0 out of 10, Exceptional, (3)
"Nice and attractive place … host has good communication "
United States
Benson-Ifere E.
The price is €124
includes taxes & fees
30 Nov - 1 Dec
Cozy 2-Bedroom Home in St-Boniface – 5 Min Walk to Food, Fuel & More

2 LUXURY BEDROOM IN BASEMENT FOR 4 PEOPLE !!!

Fort Garry
9.4 out of 10, Exceptional, (8)
"It was a quick trip and a nice place to stay! Bridgwater area is very interesting to navigate, but all in all it was decent place to stay"
Canada
Vanessa M.
The price is €107
includes taxes & fees
30 Nov - 1 Dec
2 LUXURY BEDROOM IN BASEMENT FOR 4 PEOPLE !!!

Cozy 3-Bedroom Basement Suite with Private Entrance

2.0 star property
Transcona
The price is €162
includes taxes & fees
30 Nov - 1 Dec
Cozy 3-Bedroom Basement Suite with Private Entrance

Welcoming Private 2 Bedroom Suite

Fort Garry
9.0 out of 10, Wonderful, (10)
"Thank you for a great stay. Check in was easy, the basement suite had all we needed. Excellent WiFi.New home and neighbourhood. Great place to stay. We would stay here again."
Canada
Ellie
The price is €116
includes taxes & fees
30 Nov - 1 Dec
Welcoming Private 2 Bedroom Suite

Kelvista's suite

St. Vital
9.4 out of 10, Exceptional, (10)
"A comfortable and affordable place to stay! The host is great with communication and the suite is lovely!"
Canada
Laura
The price is €118
includes taxes & fees
30 Nov - 1 Dec
Kelvista's suite

Bliss Haven

Peguis
The price is €134
includes taxes & fees
8 Dec - 9 Dec
Bliss Haven

One-bedroom guest suite with private entry

East Kildonan
10.0 out of 10, Exceptional, (5)
"Cute, clean basement suite in a quiet neighborhood. Little out of the way of amenities but easily accessible if one has a vehicle. Will stay again if ever in town and in the area"
United States
Devo A.
The price is €81
includes taxes & fees
1 Dec - 2 Dec
One-bedroom guest suite with private entry

Spacious new 3 Bedroom, sleeps 10, King Bed, 8min to YWG

2.0 star property
Deer Lodge
Spacious new 3 Bedroom, sleeps 10, King Bed, 8min to YWG

Retraite Saint Boniface/St. Boniface Retreat

Central St. Boniface
10.0 out of 10, Exceptional, (5)
"Great neighborhood and great place to stay "
Canada
jenn
The price is €178
includes taxes & fees
5 Dec - 6 Dec
Retraite Saint Boniface/St. Boniface 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

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, apart-hotels, 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 €78 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?

Afan Home of Joy: This holiday home rental outside of Headingley has air conditioning and laundry facilities 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, Beaudry Provincial Park 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.