Holiday rentals in Headingley

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Headingley

Guests agree: these stays are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1

Top guest favourite

A two-story house is set against a cloudy sky, surrounded by well-maintained green grass and trees. A pathway leads to the entrance, with a gravel trail visible to the side. The structure features a mix of light and dark siding, providing a contemporary look.

Guest suite in Headingley

4.98 out of 5 average rating, 178 reviews

Private Luxury 2 bedrooms Basement Suite Winnipeg

New Fully Furnished Basement suite This suites offer 📌 2 bedrooms (1 King Size and 1 Queen Size) 📌 1 Full washroom 📌 spacious Living Area 📌 Large Kitchen 📌 Dining area 📌 Led Tv 4K UHD 65 Inches with Netflix 📌 Separate Entrance 📌 Lit path 📌 Free 24 Hrs Parking 📌 Free WiFi Welcome to our New Suite nestled in Very peaceful neighbourhood in Blumberg Trail Just Stones throw away from Trans Canada Hyw 1. Whether you're here for a relaxing getaway our location ensures Privacy nd convenience.

Guest favourite

A modern living room features two black leather sofas and a glass coffee table set on a textured rug. A wall-mounted TV is positioned above an electric fireplace. Natural light enters through sliding doors adorned with vertical blinds, while indirect lighting adds a gentle glow to the space.

Townhouse in Winnipeg

4.79 out of 5 average rating, 209 reviews

Fast CHECK-IN 3 Bdr & 3 Beds, House.

TOP 10 WINNIPEG VACATION & HOLIDAY HOMES Our vetted home has been approved for comfort and quality. It is fully furnished, with well-equipped kitchens, luxury bathroom toiletries, and all linen included. Available for both short and long-term stays. Perfect location in a peaceful neighborhood! You will have FREE access to Wifi✔ Smart TV✔ Parking✔ Washer&Dryer✔ And much more✔ - Easy and fast access to the house via a Smart Lock - 3 Beds, 3 Bedrooms, 6 Sleeping spots - 9 am to 9 pm Support

Superhost

A modern living room is presented with a dark leather sectional sofa facing a mounted flat-screen TV. A wooden accent wall adds texture, while ambient lighting enhances the space. A small coffee table holds decorative items, and natural light filters through the window shades.

Home in Winnipeg

4.85 out of 5 average rating, 123 reviews

<New Era - Peg> Stays with Style 3brs/3queen beds

Top guest favourite

The rear view of the riverfront property showcases a spacious layout with large windows and multiple balconies. The snow-covered landscape contrasts with the earthy tones of the home, while bare trees can be seen in the surrounding area, creating a serene winter scene.

Home in Headingley

5 out of 5 average rating, 20 reviews

Private River View Family Escape

Feel the stress melt away as you enter this 4000 sq ft, private river view property with gorgeous views from every room. Step into the kitchen and warm your tired feet on the heated floors. Enjoy the natural light from the open concept kitchen, family room, dining room and skylight room. Cozy up to the natural gas fireplace in the step down family room and recline your body in the leather chairs and sectional couch. Let this be your home away from home

A bright sleeping area features a spacious bed adorned with crisp white bedding. Two neatly rolled towels are placed at the foot of the bed. Large glass doors provide natural light and lead to a balcony with views of the surrounding outdoor space.

Home in Winnipeg

4.7 out of 5 average rating, 30 reviews

Winnipeg Heaven Retreat

Welcome to your home away from home! We offer comfortable accommodation in a peaceful neighborhood. Our property features open concept living/ dining area, 3 bedrooms with comfy queen beds and 1 full bathroom. Fully loaded kitchen w/ stainless steel appliances and dishwasher. WIFI access throughout the space, Smart TVs, Netflix. Our guests can enjoy the bbq and in the spacious fenced backyard. Great for small groups or families.