Holiday rentals in Headingley

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

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

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.

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.

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.

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.

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!

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

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!