Vacation rentals in Headingley

Guest suite in Headingley

4.97 out of 5 average rating, 111 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.

5 out of 5 average rating, 59 reviews

A Keurig coffee maker is prominently displayed on a white countertop. A mug with a simple tree design sits beneath the coffee spout, ready for brewing. Several coffee pods are placed beside the machine, indicating options for guests.

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

An enclosed front porch features light-colored walls and an orange door. Two cozy chairs are positioned beside a textured pouf. Green plants hang from the ceiling, and natural light filters through large windows, creating a serene space for relaxation.

4.98 out of 5 average rating, 180 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 is presented, featuring a comfortable gray sofa paired with decorative pillows. A glass coffee table sits atop a light wooden floor. A television is positioned on a contemporary stand, with a potted plant enhancing the space's natural elements.

4.87 out of 5 average rating, 240 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.

A modern kitchen space features a sleek design with light wooden cabinetry and stainless steel appliances. A dining table is set for four, with white dishware and glassware arranged neatly. A green plant adds a touch of nature to the environment.

4.85 out of 5 average rating, 93 reviews

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

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, 7 Sleeping spots - 9 am to 9 pm Support

A cozy bedroom is presented with a spacious bed topped by a plush blanket. A flat-screen TV is mounted on the wall, and a ceiling fan is installed above. Soft gray carpet covers the floor, while dark curtains frame the windows.

4.96 out of 5 average rating, 272 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.

4.78 out of 5 average rating, 118 reviews

A modern two-story building features a combination of neutral and warm exterior tones. Large windows are visible, allowing natural light to fill the interior. The pathway is lined with gravel, leading to the entrance at the front of the structure, flanked by two adjacent homes.

Guest suite in Winnipeg

2022 House Build! Entire suite! 2 Queen Beds!

Welcome to your home away from home. Here you will enjoy your own private 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.

A modern kitchen and dining area features stainless steel appliances, an island with seating, and a dining table surrounded by six chairs. Natural light fills the space from nearby windows, highlighting the wooden flooring and minimalist decor.

4.82 out of 5 average rating, 62 reviews

New Renovated Home With Jacuzzi

Our carefully inspected property has been approved for both comfort and quality. It is completely outfitted with upscale bathroom fixtures and fully functional kitchens. Fantastic location in a calm And really handy place! Free street parking, be aware that the City sometimes can prohibit the parking for the night because of the snow removal, etc, Among other things, a washer and dryer. - Easy and quick access to the house with a smart lock 9 a.m. to 9 p.m.: Assistance is offered.

A spacious living area is presented with a light-colored sectional sofa adorned with cushions in various patterns. A round coffee table and a small accent table are positioned on a rug over hardwood flooring. Natural light enters through large windows, complemented by several indoor plants.

4.8 out of 5 average rating, 35 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.

4.99 out of 5 average rating, 72 reviews

A modern home is showcased with a grey exterior and a contrasting dark roof. A small porch features a white chair, and an elegant door is framed by a light fixture. A driveway and landscaped area with shrubs and flowers are visible.

Guest suite in Winnipeg

The OG Guest Expertise Luxury 2 Bedroom Retreat

Luxurious Stay Perfect for Group Trips Only 5 minutes from No Frills and Walmart Nearby access to Outlet Mall, Ikea, community center, parks, golf course, YMCA, restaurants, shopping, and hotels. Nestled in a truly beautiful and peaceful neighborhood. Access to the basement is through the main door, but a separate entrance maintains your privacy. Please note my family resides in the main part of the house. Ready to relax in style and convenience? Book your stay today!

4.83 out of 5 average rating, 46 reviews

A modern kitchen is visible, featuring a sleek countertop set for a meal with plates, glasses, and a variety of food items. An array of fresh fruits sits in a bowl, while snowy views can be seen through the windows.

Bungalow in Winnipeg

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!

Guest favorite

A wooden serving tray displays a white coffee canister alongside two glass jars. One jar contains sugar, while the other holds assorted tea bags and condiments. Fresh yellow flowers add a touch of color, enhancing the kitchen's inviting atmosphere.

4.83 out of 5 average rating, 76 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!

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Other great vacation rentals in Headingley

The open concept kitchen showcases modern cabinetry and sleek countertops. Six bar stools are arranged around the island. Natural light fills the space, highlighting the appliances and fixtures. The layout extends into a living area visible through large glass doors, creating a sense of connection.

4.86 out of 5 average rating, 65 reviews

Contemporary Bliss: 3 Bedroom Retreat

RebeccaRating, 5 stars1 week ago

Great space for a family of 6. Plenty of room for everyone.

A cozy sleeping area is presented with a spacious bed dressed in dark bedding, paired with red pillows. A single black chair is positioned nearby, next to a large mirror reflecting the soft floral wallpaper and wooden flooring.

4.77 out of 5 average rating, 632 reviews

crestview park #1

BethanyRating, 5 stars3 weeks ago

My son loved the air hockey table, we will definitely be coming here more often when we are in the city! Really nice place with good air quality, nice and cool, not hot.

A spacious bed is featured with patterned bedding in neutral and bold colors, complemented by a set of rolled towels. A striking red accent wall is present, alongside a wall art piece depicting a red barn in a snowy landscape. Soft lighting is provided by hanging fixtures.

Private room in Winnipeg

5 out of 5 average rating, 3 reviews

The Barn Room

AminRating, 5 stars24 months ago

experience from the Airbnb host.. Mr George and Mrs Clyde are humble and respectful hosts. the place it was clean, mint, and roomy. I definitely will come back to that place.. Mr George and Clyde know how to treat their guest.. if you are looking for an Airbnb, I recommend it for you, and you will thank me for this recommendation. please, if you are looking for airbnp in Winnipeg, that is the place for you.. Mr. George and his family know how to treat guests like a family.. thanks, not enough for this family!!