Headingley Holiday Rentals from €78: Search Short-Term Rentals

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Holiday Rentals in Headingley

Cozy living space with a kitchenette, featuring a sofa, coffee table, and small dining area.

Relax in this stylish living room with a sofa, coffee table, and potted plant.

Cozy living space with a kitchenette, sofa, and flat-screen TV.

"We had a nice week-long stay in Winnipeg at this Vrbo. The host was easy to communicate with. The suite covered all the basics needed. Thank you."

includes taxes & fees

17 Jul - 18 Jul

Secure entrance with a modern door and clean design.

"We enjoyed our 4-day stay, it was very clean, in a new home, quiet and spacious, and our hosts were very accomodating."

includes taxes & fees

6 Aug - 7 Aug

Cozy living space with a sofa, side table, and modern kitchen area.

includes taxes & fees

15 Jul - 16 Jul

Enjoy cooking in this well-equipped kitchen with a microwave, dishwasher, and double sink.

includes taxes & fees

21 Jul - 22 Jul

Stunning two-story home with a garage and inviting front porch.

includes taxes & fees

21 Jul - 22 Jul

Stylish building with a dark grey accent wall and white-framed windows.

includes taxes & fees

19 Jul - 20 Jul

Cozy living space with a central seating area, kitchen counter, and potted plant.

includes taxes & fees

22 Jul - 23 Jul

Cozy retreat with a single bed, nightstand, and bedside table, featuring a window with blue curtains.

includes taxes & fees

15 Jul - 16 Jul

Fully equipped kitchen with integrated appliances, coffee maker, kettle, toaster, and sink.

"This property was amazing would love to stay here again "

includes taxes & fees

11 Aug - 12 Aug

Enjoy cooking in this well-equipped kitchen with a toaster and coffee maker.

"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."

includes taxes & fees

15 Jul - 16 Jul

Prepare meals in a sleek kitchen with dark cabinetry and stainless steel appliances.

includes taxes & fees

22 Jul - 23 Jul

Enjoy cooking in this well-equipped kitchen with a microwave, refrigerator, sink, and ample countertop space.

"Great location, easy access, everything you need."

includes taxes & fees

20 Jul - 21 Jul

Enjoy cooking in this well-equipped kitchen with a microwave, refrigerator, sink, and coffee maker.

"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."

includes taxes & fees

18 Jul - 19 Jul

Restful retreat with a large bed, nightstand, and wardrobe.

includes taxes & fees

15 Jul - 16 Jul

Enjoy meals in this dining area with a round table for four, featuring white chairs and a tablecloth.

"Easy to find, efficient check in and communication with host. The space was exactly as advertised. Would highly recommend."

includes taxes & fees

15 Jul - 16 Jul

includes taxes & fees

17 Jul - 18 Jul

Stroll along the winding pathway to a charming wooden staircase.

"The suite was located on a quiet street but close to a main street so it was easy getting around. It was sparsely furnished and could have used extra bath towels, face clothes, and blankets. The floor under the bed needs be to be thoroughly cleaned. Considering the affordable cost, it was a good value overall."

includes taxes & fees

26 Jul - 27 Jul

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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.

Recent reviews of Headingley properties

5/5 Excellent

"The gold concierge desk and lounge really made the difference for us this stay. The view was beautiful and we felt well taken care of. They made our anniversary extra special! "

A verified traveller from Edmonton stayed at The Fairmont Winnipeg

Posted 7 hours ago

5/5 Excellent

Nice, very clean and charming place in the center

"The front desk receptionists were very helpful. Not only did they help us check in quickly, they also gave us very good advice on sight seeing locations and food. Anytime I go to Winnipeg, this will be the place I want to stay. It is not an expensive place but it does have a slightly old, beautiful and charming ambience. "

A verified traveller stayed at Humphry Inn & Suites

Posted 2 days ago

The Fort Garry Hotel, Spa and Conference Centre, Ascend Hotel Collection

5/5 Excellent

"Check in (Lydia) was so kind and helpful. Bar service was outstanding. Maintenance (Manny and Sergio) helped me with a wee problem. The whole experience was amazing. "

A verified traveller stayed at The Fort Garry Hotel, Spa and Conference Centre, Ascend Hotel Collection

Posted 3 days ago

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?

Cheerful Tuxedo House with Hot Tub : This holiday home rental outside of Headingley offers a fireplace, 1 hot tub and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 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 Golf Course and John Blumberg Softball Complex 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.

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Holiday Rentals in Headingley

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Holiday Rentals in Headingley

Luxury: Home Away from Home with Private Entrance

Furnished basement with seperate entrance ,living room,washroom and kitchenette

Charming 2-bedroom basement in brilliant Winnipeg with WiFi, AC

Afan Home of Joy

Nice 2 bed basement + private entrance

Bliss and Comfort Home

Elegant bedroom in Winnipeg

Modern Basement Suite with Private Entrance - Perfect for a Relaxing Stay!

The Snug Spot,Retreat offers a warm and inviting escape for travelers.

Cozy Family-Friendly 1BR Apartment /Downtown Free Parking,Wi-Fi, Balcony,Laundry

Kelvista's suite

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

Private Basement Apartment with separate entrance

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

Amazing 2 bedroom basement with separate entrance

Suite with facilities to make you feel at home

One-bedroom guest suite with private entry

Amazing 4 Bedrooms Entire Home in Winnipeg with Free parking, Wi-fi and more

Winnipeg Radiant Home - A peaceful neighborhood with separate entrance

Find out more about Headingley

Recent reviews of Headingley properties

The Fairmont Winnipeg

Best Western Plus Winnipeg West

Radisson Hotel Winnipeg Downtown

Motel 6 Headingley, MB - Winnipeg West

Travelodge by Wyndham Winnipeg East

Humphry Inn & Suites

The Fort Garry Hotel, Spa and Conference Centre, Ascend Hotel Collection

Lakeview Signature, Trademark Collection by Wyndham

The Grand Winnipeg Airport Hotel by Lakeview

Frequently asked questions