Vacation rentals in Headingley

Guest suite in Headingley

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.

4.98 out of 5 average rating, 163 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.

4.79 out of 5 average rating, 205 reviews

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

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

A modern living area features a gray sectional sofa and a colorful red chair. A light wood coffee table is centered in front of a large flat-screen TV mounted on the wall. Two windows allow natural light to illuminate the space, enhanced by soft neutrals and warm accents.

4.95 out of 5 average rating, 76 reviews

Spacious new 3BR, sleeps 10, King Bed, 8min to YWG

Relax in this brand-new cozy home in St James, just minutes from Winnipeg Airport, downtown, Polo Park, and Assiniboine Park. This stylish space offers a King bed, 2 Queens, and a sofabed, sleeping 10 comfortably. Enjoy a fully stocked kitchen, dining for 6, 4 high chairs, and free parking in a quiet neighborhood near top restaurants & shopping. Perfect for large families, professionals, medical workers, tourists, or solo travelers, this home provides a relaxing retreat for every kind of guest

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.

4.94 out of 5 average rating, 100 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

5 out of 5 average rating, 68 reviews

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

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

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.

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.

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.

4.96 out of 5 average rating, 328 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.

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.

4.92 out of 5 average rating, 159 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.

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.

4.82 out of 5 average rating, 102 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.

5 out of 5 average rating, 15 reviews

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

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

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.

4.82 out of 5 average rating, 89 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!

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.