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, 155 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 modern two-story home with a sleek exterior design features large front windows and warm wooden accents. A black railing lines the steps leading to the front door, providing easy access. The surrounding area includes grassy patches waiting for landscaping.

Home in Winnipeg

4.94 out of 5 average rating, 99 reviews

Kid-Friendly Stay | Near Zoo, Mall & Downtown

Welcome to your cozy and convenient family-friendly getaway! 7 minutes from the airport and 5 minutes to Polo Park Mall. Enjoy easy access to: Downtown & Canada Life Centre (15 min) The Forks, museums & historic sites, Assiniboine Park & Zoo, Sargent Sundae (5–10 min drive). St. James Civic Centre (with pool) – just a 15-minute walk! With a quiet neighborhood setting, plenty of nearby parks, and child-friendly features, this home is perfect for families, business travelers, or weekend explorers

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, 67 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, 188 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.

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, 317 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.

Top guest favorite

A modern two-story private suite is shown, featuring a blend of textured materials on the exterior. Large windows provide natural light to the interior, while a gravel pathway leads to the entrance. The neighboring buildings display similar architectural styles.

Home in Winnipeg

4.92 out of 5 average rating, 156 reviews

2022 House Build! 3 King Beds 2.5 Baths!

Welcome to your home away from home. This is a newer build, 2 storey private suite. All 3 bedrooms are furnished with king 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. This open concept suite comes equipped with everything you need to make your stay enjoyable, including Netflix and in suite laundry.

Guest favorite

A modern living and dining area is depicted, featuring a spacious grey sectional sofa and a dark coffee table. A dining table with colorful chairs offers seating. Soft natural light enters through large windows, complemented by neutral walls and stylish artwork.

Home in Winnipeg

4.82 out of 5 average rating, 99 reviews

Winnipeg Top Stay

Welcome to your home away from home! We offer comfortable accommodation in the perfect spot. Our property features high end modern, open concept living area, 3 bedrooms with comfy queen beds and 2 full bathrooms. Fully loaded kitchen w/ high-end stainless steel appliances and dishwasher. WIFI access throughout the space, Smart TVs, Netflix. Lots of vanity counter space! Our guests can enjoy the bbq and in the spacious backyard. Great for small groups or families.

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

Guest favorite

A modern living area features a low wooden coffee table at the center, surrounded by a black leather sofa and a stylish armchair. A potted plant adds a touch of greenery, while soft lighting enhances the warm ambiance, complemented by patterned area rugs and textured curtains.

Home in Winnipeg

4.82 out of 5 average rating, 88 reviews

Spacious 3 Bedroom Private Suite with 5 beds!

The PERFECT family getaway! This stylish bungalow has plenty of space for your family to enjoy while staying in Winnipeg. Located on a quiet street in the Charleswood area of Winnipeg with a public pool, and park just across the street, the house is only minutes away from Ikea, the Outlet Collection, Polo Park Shopping Center and the Trans Canada Highway, making this the perfect stop over on your way through Winnipeg!

Top guest favorite

A play area is equipped with a climbing structure and various toys, offering fun for children. In another image, a spacious bed is arranged with fresh linens and neatly folded towels, complemented by a mirror reflecting the room's decor. A dining setup displays elegantly arranged glassware and table settings. The living room features a comfortable seating area with a Smart TV and decorative fireplace.

Home in Winnipeg

4.98 out of 5 average rating, 41 reviews

Forest Haven by Assiniboine

Bring the whole family to this great place with lots of room for fun. Stay in this spacious 3-bedroom home with 2 queen and 1 king beds, 2 full baths, perfectly located next to Assiniboine Forest. Enjoy a peaceful retreat surrounded by nature, with nearby walking trails and all the comforts of home. Ideal for families, couples, or small groups looking for a relaxing getaway. Book now for the perfect escape!

Top guest favorite

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, 6 reviews

Oakview Estate – 5BR Suite by Guest Expertise

Top 10 Winnipeg Vacation Home – Luxury, Space & Comfort Luxury 5-Bedroom Oakview Estate welcomes families & teams seeking space, privacy and style. What you’ll love: Chef-ready kitchen & outdoor kitchen for group meals Backyard with dining area & dedicated workspace Smart TV, fast Wi-Fi, washer & dryer Minutes to Winnipeg attractions and conveniences. Book now to secure your stay!