Vacation rentals in Headingley

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Top-rated vacation rentals in Headingley

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Top guest favorite

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, 141 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 favorite

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

4.78 out of 5 average rating, 203 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

Top guest favorite

A cozy bedroom is shown featuring a wooden bed with a softly layered quilt and decorative pillows. Each side of the bed is complemented by modern bedside lamps, and a calming landscape artwork adorns the wall above the headboard, enhancing the room's tranquil ambiance.

Guest suite in Winnipeg

5 out of 5 average rating, 64 reviews

Guesthouse By The Park

Welcome to The Guesthouse By The Park! The fully renovated 1 bdr suite is a few steps from Assiniboine Park, home to the Zoo, The Leaf, Park Cafe, shows, events and several attractions. Whether you are looking for a place to work, study or just chill, this unit in the basement of our home offers the right balance of modern and cozy. We will be happy to be your hosts in Winnipeg!! *rates depend on number of guests/nights- please make sure this information is accurate in your booking request

Top guest favorite

A lofted space features a workspace with a sleek chair beside a small desk. Neutral tones dominate the area, with a macramé wall hanging adding texture. The adjoining bedroom is visible through an open door, showcasing a queen bed made with light bedding.

Home in Winnipeg

4.98 out of 5 average rating, 186 reviews

Albany Cottage: loft bedroom and close to airport

Take it easy at this cottage style home located on a quiet residential street just 10 minutes west of Downtown Winnipeg and 5 minutes from the James Armstrong Richardson International Airport. Albany Cottage, built in 1907, offers a loft bedroom and office plus a breezy boho porch for enjoying your morning coffee. Public transportation and bike/walking trails are right at the end of the street, and you are a 10-minute walk from one of Winnipeg's most popular public spaces, Assiniboine Park.

Guest favorite

A modern living area features a gray sectional sofa adorned with patterned cushions. A round coffee table rests on a soft area rug, accompanied by a wooden TV stand. Natural light enters through large windows, framed by sleek blinds and potted plants positioned nearby.

Guest suite in Winnipeg

4.78 out of 5 average rating, 126 reviews

2022 House Build! Entire suite! 2 Queen Beds!

Welcome to your home away from home. Here you will enjoy your own private basement suite in this newer build. Both bedrooms are furnished with queen beds. Walking distance to some of Winnipeg's finest attractions including Assiniboine Park/Zoo, Sargent Sundae and just a few doors down from The Burger Place. Minutes away from Polo Park shopping mall, groceries and restaurants. The suite comes equipped with everything you need to make your stay enjoyable, including Netflix and in suite laundry.

Guest favorite

A modern living area features a comfortable gray sofa with decorative cushions, a glass coffee table, and a TV stand. Natural light filters through sheer window coverings, and a dining table with chairs is visible in the background, enhancing the spacious atmosphere.

Home in Winnipeg

4.87 out of 5 average rating, 243 reviews

Cozy St. James Home

Very Clean house with 3 Bedrooms, 1 Bath and a fenced yard. Comes With everything you need to be your home away from home ! It is located in a mature neighborhood that is a 3 Minute drive to Polo park Shopping center, other shopping stores and restaurants. 10 minute drive to Canada Life Center(Jets), U of W and the Forks ! The Airport is also a 5 minute drive away ! It is also walking distance of Major bus routes, convenience stores and Grocery stores, Kids Parks, Assiniboine Park and more.

Top guest favorite

A modern living area features a sleek white sofa and two round coffee tables arranged on a light-colored rug. Natural light filters through a large window, revealing views of street activity. A decorative plant adds a touch of greenery, and a mounted TV complements the space.

Apartment in Winnipeg

4.96 out of 5 average rating, 24 reviews

Great location with 3 bedrooms and 4 beds

Bring the whole family to this great place with lots of room for fun and relaxation. Or make it your luxury office away from home with all the amenities. This condominium located in Silver Heights is near airport and Polo park. Only a short drive from downtown. This property brings classic design with new furnishings. The kitchen is very functionable and spacious. There are two parking spots available and free parking on the street. Located close to restaurants, groceries, gas and more.

Top guest favorite

A spacious bedroom is highlighted by a large bed with a dark headboard and soft bedding. Natural light filters through a window, framed by dark curtains. A small desk and lamp are positioned nearby, while recessed lighting enhances the overall ambiance.

Home in Winnipeg

4.96 out of 5 average rating, 299 reviews

Entire Suite in Crestview

Welcome to our amazing new suite nestled in a peaceful neighborhood in Crestview, just a stone's throw away from Winnipeg's finest dining establishments and shopping centers. Whether you're here for a relaxing getaway or a business trip, our location ensures convenience and tranquility. Situated a mere 15-minute drive from Winnipeg Airport and Polo Park, our suite is easily accessible. As part of a new duplex-style home, this unit offers complete privacy with its own separate entrance.

Superhost

A modern living room is presented with a light-colored sofa adorned with several pillows, including a deep blue one. A small coffee table is visible alongside a potted plant. Accents like ottomans in blue and white stripes complement the inviting atmosphere.

Home in Winnipeg

4.83 out of 5 average rating, 42 reviews

Bungalow House Winnipeg -Short Term Rental

Kick back and relax in this calm, stylish space. Enjoy a stylish experience at this centrally located place. Accessible for both transient and long-term stays. Excellent location in a calm but extremely convenient neighborhood! Welcome to your temporary residence! The full house at our tastefully furnished Airbnb is ideal for a convenient and comfortable short or long stay. This house provides everything you need to feel at home, whether you're traveling for work or pleasure.

Superhost

A spacious living area features a large sectional sofa and a wooden coffee table. A vibrant mural of mountains and trees decorates one wall, enhancing the natural ambiance. A flat-screen TV is mounted for entertainment, with dining stools positioned nearby for casual gatherings.

Bungalow in Winnipeg

4.84 out of 5 average rating, 50 reviews

Banff-Themed King Size Retreat

Welcome to our Airbnb listing for Winnipeg! Our modest home in the quaint Charleswood area with a rustic Banff-inspired interior that transports you to the Rockies right in the middle of the city. Unwind in our inviting living room, which features plush armchairs and a big flat-screen TV. Your group will have enough room in the dining area, and the fully equipped kitchen is ideal for creating delectable meals. We wish you a relaxing and memorable stay with us!

Top guest favorite

A serene river view is featured, showcasing the calm waters reflecting colorful sunset hues. The landscape is framed by trees on the opposite bank and soft grass lining the shore. A hummingbird feeder hangs from the house, adding a touch of nature to the scene.

Home in Headingley

5 out of 5 average rating, 15 reviews

Private River View Family Escape

Feel the stress melt away as you enter this 4000 sq ft, 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

Superhost

The exterior view of the home highlights a modern façade with neutral tones and clean lines. A spacious driveway provides access to a garage, while a manicured lawn and decorative landscaping enhance the curb appeal. A welcoming entryway is flanked by tasteful greenery.

Home in Winnipeg

5 out of 5 average rating, 3 reviews

Oakview Estate by Guest Expertise

Top 10 Winnipeg Vacation Home – Luxury, Space & Comfort This stunning 5-bedroom, 3-bathroom home offers comfort, space, and style. Enjoy a full kitchen, open living areas, a finished basement, backyard patio, and front lawn. Located in a quiet upscale neighborhood—just 5 minutes to No Frills, Walmart, outlet mall, Ikea, parks, YMCA, restaurants, and more. Perfect for vacations, business trips, or getaways. Book your stay today!