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Our top choices for Headingley holiday rentals

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 £84
includes taxes & fees
8 Feb - 9 Feb
Golden Eagle, Basement Suite

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 £129
includes taxes & fees
20 Feb - 21 Feb
Amazing 2 bedroom basement with separate entrance

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 £80
includes taxes & fees
9 Feb - 10 Feb
Exquisite 1-bedroom basement in the quiet neighbourhood of Bonavista, Winnipeg

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 £105
includes taxes & fees
9 Feb - 10 Feb
AVOCADO EXECUTIVE SUITES

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 £232
includes taxes & fees
10 Feb - 11 Feb
St. Thérèse’s Nest: Your Peaceful Retreat Minutes from the Pulse of the City

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 £83
includes taxes & fees
8 Feb - 9 Feb
Charming Bedroom in Bonavista

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 £70
includes taxes & fees
8 Feb - 9 Feb
Morning glory cottage

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 £66
includes taxes & fees
15 Feb - 16 Feb
The perfect Retreat

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 £91
includes taxes & fees
20 Feb - 21 Feb
Private Basement Apartment with separate entrance

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 £100
includes taxes & fees
8 Feb - 9 Feb
Afan Home of Joy

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 £87
includes taxes & fees
12 Feb - 13 Feb
2 LUXURY BEDROOM IN BASEMENT FOR 4 PEOPLE !!!

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 £161
includes taxes & fees
9 Feb - 10 Feb
Prairie Luxury 2 Bedrooms Home

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 £62
includes taxes & fees
20 Feb - 21 Feb
One-bedroom guest suite with private entry

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 £103
includes taxes & fees
8 Feb - 9 Feb
Avocado Executive Suite 1

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 £70
includes taxes & fees
1 Mar - 2 Mar
Luxury 2-bedroom living in St. Vital, St Mary's, St Anne's, Winnipeg.

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 £72
includes taxes & fees
9 Feb - 10 Feb
Serenity meets class: Entire Basement Suite in Winnipeg

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 £83
includes taxes & fees
9 Feb - 10 Feb
Elegant 1-Bedroom Basement Suite

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 £77
includes taxes & fees
9 Feb - 10 Feb
Cozy Haven 1-bedroom suite close to centre of Winnipeg

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 £149
includes taxes & fees
9 Feb - 10 Feb
Urban-Peg: Modern Comfort in the Heart of the City

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 £95
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

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 £73 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?

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.