Headingley Holiday Rentals

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Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Our top choices for Headingley holiday rentals

Exterior

Golden Eagle, Basement Suite

Golden Eagle, Basement Suite
Winnipeg
10.0 out of 10, Exceptional, (3 reviews)
"The host was really.nice and respectful, he is on top for respond to my needs concerning any supplies for my stay,, I just only want he be lenient a little with the guess for small details ( s.all hair in the bathroom/ carpet/ bed) after that I give 5 stars, and highly recommended. "
United States
Lesly
The price is HK$443
HK$867 total
includes taxes & fees
8 Feb - 9 Feb
Golden Eagle, Basement Suite
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 HK$1,029
HK$1,457 total
includes taxes & fees
6 Mar - 7 Mar
Amazing 2 bedroom basement with separate entrance
Smart TV

Exquisite 1-bedroom basement in the quiet neighbourhood of Bonavista, Winnipeg

Exquisite 1-bedroom basement in the quiet neighbourhood of Bonavista, Winnipeg
St. Vital
10.0 out of 10, Exceptional, (2 reviews)
"Overall enjoyed my stay the place was well kept and completely hosted myself and two friends for the weekend. In a great neighborhood felt safe and a beautiful park walking distance away. I recommend it’s comfortable and affordable."
Canada
Hana S.
The price is HK$371
HK$815 total
includes taxes & fees
17 Feb - 18 Feb
Exquisite 1-bedroom basement in the quiet neighbourhood of Bonavista, Winnipeg
Interior

AVOCADO EXECUTIVE SUITES

AVOCADO EXECUTIVE SUITES
St. Vital
8.0 out of 10, Very good, (3 reviews)
"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 HK$489
HK$1,089 total
includes taxes & fees
6 Mar - 7 Mar
AVOCADO EXECUTIVE SUITES
Interior

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

St. Thérèse’s Nest: Your Peaceful Retreat Minutes from the Pulse of the City
Lord Roberts
10.0 out of 10, Exceptional, (1 review)
"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 HK$928
HK$2,477 total
includes taxes & fees
6 Feb - 7 Feb
St. Thérèse’s Nest: Your Peaceful Retreat Minutes from the Pulse of the City
Exterior detail

Charming Bedroom in Bonavista

Charming Bedroom in Bonavista
St. Vital
8.0 out of 10, Very good, (2 reviews)
"The place was very clean and very very new. There was still the stickers from original packaging on the TV and some appliances. Apparently the laundry room is locked and you are only given access if you stay 4 nights. This was not made clear when booking. I was also under the impression that I was renting the whole house and that the second bedroom could be rented if I chose so. However, j found out that there would be a person I didn't know who rented out the slate bedroom. Luckily, the owner...
United States
Wesley R.
The price is HK$400
HK$849 total
includes taxes & fees
6 Mar - 7 Mar
Charming Bedroom in Bonavista
Exterior

Morning glory cottage

Morning glory cottage
Peguis
8.6 out of 10, Excellent, (40 reviews)
"Good place to stay, only thing missing would be a stove or cooktop to be perfect "
Canada
Jhonas T.
The price is HK$371
HK$714 total
includes taxes & fees
6 Feb - 7 Feb
Morning glory cottage
Interior

The perfect Retreat

The perfect Retreat
Peguis
8.4 out of 10, Very good, (5 reviews)
"Owner was very friendly and house was well maintained "
Canada
Erik
The price is HK$343
HK$714 total
includes taxes & fees
8 Mar - 9 Mar
The perfect Retreat
Smart TV, fireplace

Private Basement Apartment with separate entrance

Private Basement Apartment with separate entrance
St. Vital
10.0 out of 10, Exceptional, (1 review)
"Perfect for a 1 night stay. Just passing through. "
Canada
Norman
The price is HK$629
HK$1,011 total
includes taxes & fees
13 Feb - 14 Feb
Private Basement Apartment with separate entrance
Exterior detail

Afan Home of Joy

Afan Home of Joy
Peguis
9.6 out of 10, Exceptional, (22 reviews)
"This is a wonderful space and we enjoyed our time staying here. Will would definitely stay again!"
Canada
Desiree R.
The price is HK$500
HK$1,036 total
includes taxes & fees
6 Feb - 7 Feb
Afan Home of Joy
Property grounds

2 LUXURY BEDROOM IN BASEMENT FOR 4 PEOPLE !!!

2 LUXURY BEDROOM IN BASEMENT FOR 4 PEOPLE !!!
Fort Garry
9.4 out of 10, Exceptional, (8 reviews)
"We had a great stay! Hosts were communicative and we have nothing but good things to say about property itself."
Canada
Aidan M.
The price is HK$437
HK$893 total
includes taxes & fees
18 Feb - 19 Feb
2 LUXURY BEDROOM IN BASEMENT FOR 4 PEOPLE !!!
Exterior

Prairie Luxury 2 Bedrooms Home

Prairie Luxury 2 Bedrooms Home
Fort Garry
9.4 out of 10, Exceptional, (6 reviews)
"Great space. Host was very responsive to our requests."
Canada
Bels45
The price is HK$474
HK$1,715 total
includes taxes & fees
9 Feb - 10 Feb
Prairie Luxury 2 Bedrooms Home
Interior

One-bedroom guest suite with private entry

One-bedroom guest suite with private entry
East Kildonan
10.0 out of 10, Exceptional, (6 reviews)
"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 HK$299
HK$629 total
includes taxes & fees
13 Feb - 14 Feb
One-bedroom guest suite with private entry
Interior

Avocado Executive Suite 1

Avocado Executive Suite 1
St. Vital
8.0 out of 10, Very good, (1 review)
"Only thing there wasn’t an oven. Had a couple of issues but they were resolved quickly "
Canada
Craig B.
The price is HK$468
HK$1,065 total
includes taxes & fees
9 Feb - 10 Feb
Avocado Executive Suite 1
Interior

Luxury 2-bedroom living in St. Vital, St Mary's, St Anne's, Winnipeg.

Luxury 2-bedroom living in St. Vital, St Mary's, St Anne's, Winnipeg.
St. Vital
The price is HK$389
HK$634 total
includes taxes & fees
6 Feb - 7 Feb
Luxury 2-bedroom living in St. Vital, St Mary's, St Anne's, Winnipeg.
Interior

Serenity meets class: Entire Basement Suite in Winnipeg

Serenity meets class: Entire Basement Suite in Winnipeg
St. Vital
9.0 out of 10, Wonderful, (11 reviews)
"Excellent accommodations, great communication with host, everything was easy. You definitely could hear the family upstairs so know that going in but if you’re okay with that - this is a great stay and we would recommend it!"
United States
Shanna M.
The price is HK$334
HK$737 total
includes taxes & fees
18 Feb - 19 Feb
Serenity meets class: Entire Basement Suite in Winnipeg
Exterior

Elegant 1-Bedroom Basement Suite

Elegant 1-Bedroom Basement Suite
St. Vital
9.4 out of 10, Exceptional, (3 reviews)
"Well maintained clean property. The owner of the home was very accomodating and kind. Great location. Felt like home during our stay! Will definitely come back."
Canada
Sameh
The price is HK$343
HK$849 total
includes taxes & fees
13 Feb - 14 Feb
Elegant 1-Bedroom Basement Suite
Living area

Cozy Haven 1-bedroom suite close to centre of Winnipeg

Cozy Haven 1-bedroom suite close to centre of Winnipeg
Winnipeg
10.0 out of 10, Exceptional, (2 reviews)
"Would definitely stay here again if I’m ever in Winnipeg! "
Canada
Ashton P.
The price is HK$438
HK$793 total
includes taxes & fees
10 Feb - 11 Feb
Cozy Haven 1-bedroom suite close to centre of Winnipeg
Dishwasher, blender

Urban-Peg: Modern Comfort in the Heart of the City

Urban-Peg: Modern Comfort in the Heart of the City
Norwood East
9.8 out of 10, Exceptional, (6 reviews)
"It was perfect for us to visit our family and it's a verry quiet place. I see deer in the morning we enjoy our stay! "
Canada
Linda R.
The price is HK$653
HK$1,560 total
includes taxes & fees
7 Feb - 8 Feb
Urban-Peg: Modern Comfort in the Heart of the City
Private kitchen

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

Cozy 2-Bedroom Home in St-Boniface – 5 Min Walk to Food, Fuel & More
Central St. Boniface
10.0 out of 10, Exceptional, (3 reviews)
"Nice and attractive place … host has good communication "
United States
Benson-Ifere E.
The price is HK$515
HK$986 total
includes taxes & fees
9 Feb - 10 Feb
Cozy 2-Bedroom Home in St-Boniface – 5 Min Walk to Food, Fuel & 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

Best Western Plus Winnipeg West

Best Western Plus Winnipeg West

10/10 Excellent
"Nice"
Dilip 3-night trip
Posted 1 day ago
Best Western Plus Winnipeg West

Find out more about Headingley

Search for holiday rentals in Headingley on Expedia! You can easily find your home rentals, villas, holiday apartments in Headingley using one of the methods below:

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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?

3000 sq.ft 5 Beds , 4 bedrooms 3 Full bath Spacious Clean Home: This holiday home rental outside of Headingley offers a fireplace, a patio and a BBQ 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 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 Golf Course and Beaudry Provincial Park 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.