Holiday rentals near WinSport

We found 2,594 holiday rentals — enter your dates for availability

Find the perfect holiday rental within close proximity to WinSport. Holiday rentals provide the best amenities for you and your friends, family or even pets, such as Wi-Fi and parking. What you'll find is a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - WinSport

Showing deals for:31 July - 7 Aug

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Frequently asked questions

What are the best holiday rentals near Winsport?
The best holiday rentals near Winsport are primarily located in Southwest Calgary, offering convenient access to the facility. You will find a great selection of properties here, with private holiday houses being the most common, followed by apartments. If you are willing to drive a bit further, renting in nearby areas can be an affordable option for finding larger properties. You can choose from a range of styles so you can have a comfortable stay. When looking for the best holiday rentals near Winsport, consider homes that are easily accessible to the area.

Many top-rated rentals feature amenities for a pleasant stay, such as a balcony for outdoor enjoyment, a desk for remote work, and laundry facilities. These homes are ideal for solo travellers or small families.
Are there any cheap holiday rentals near Winsport?
There are several affordable holiday rentals near Winsport, especially if you are flexible with location and travel dates. Budget-friendly stays are typically around AU$95 per night in areas like Southwest Calgary. Some stays even drop below that in November and February during the off-season, making it a great option for guests looking to experience the area without overspending. These rentals often include free amenities such as WiFi, toiletries, and self-parking, and can range from cosy studio apartments to modest family homes, providing a clean, comfortable base for adventure.

To get the best value, consider staying slightly outside major hubs. If you're willing to drive a bit further, renting around nearby areas can be an affordable option. With a little planning, it is absolutely possible to find a comfortable stay near Winsport while keeping costs down.

*Pricing data are based on past 12 months data.
What are the top holiday rentals with pools near Winsport?
Several holiday rentals near Winsport offer access to swimming pools, primarily featuring shared indoor options within apartment and condo properties. These properties are concentrated in Southwest Calgary, providing guests with convenient access to Winsport. Most rentals come with standard amenities such as fully equipped kitchens, comfortable living areas, and Wi-Fi, making them suitable for families or groups seeking a comfortable stay.

When selecting your ideal rental, consider the benefits of shared indoor pools, which often include access to additional facilities like fitness centres. Given Calgary's climate, indoor pools are a fantastic option for year-round enjoyment, ensuring a refreshing dip is always available regardless of the weather.
What are the best family holiday rentals near Winsport?
There are over 50 family-friendly holiday homes available in Southwest Calgary, near Winsport, offering ample space and comfort for groups. These properties often feature multiple bedrooms and bathrooms, full kitchens for preparing meals, and outdoor play areas such as gardens or patios. Many also provide washer/dryers, and entertainment options like video games or books for both adults and children.

When selecting a home, prioritise rentals that offer separate spaces for adults and children to relax, and look for practical amenities like well-equipped kitchens and laundry facilities to simplify your stay. Choosing a property close to Winsport means less travel time and more opportunity to enjoy the activities.
Are there any luxury holiday rentals near Winsport?
There are several luxury holiday rentals near Winsport that combine mountain scenery with modern comfort. These properties often feature amenities such as fireplaces, air conditioning, and mountain views. Guests can also find properties with golf and tennis facilities on-site, providing active leisure options.

These homes are ideal for families or larger groups, offering amenities like high-speed WiFi for a comfortable stay. Many of these top-tier stays are managed by highly rated Stayz hosts, ensuring a professional and premium experience.
How much is a holiday rental near Winsport?
Holiday rentals near Winsport offer a wide range of options to suit different budgets, making it easy for guests to enjoy a memorable stay. Budget-friendly properties typically start around AU$95 per night, providing an affordable option. Mid-range rentals, including private homes, are generally around AU$185 per night, offering more comfort and privacy. For those seeking a more luxurious experience, upscale options can cost AU$300 or more per night.

Enter your destination, travel dates, and number of guests on search to see the best options. You can use filters to set a minimum and maximum nightly price range along with other preferences. Rates may vary based on the season and specific amenities, but with a little planning, guests can find a rental that perfectly balances convenience and value.

*Pricing data are based on past 12 months data.
Where should I stay when visiting Winsport?
When visiting Winsport, several excellent areas offer convenient access and a variety of holiday rental experiences.

The Bowness neighbourhood, located just to the north of Winsport, offers a charming, established community feel. Properties here provide easy access to Winsport and the beautiful Bowness Park, which features river pathways and recreational activities. It's a great choice for guests seeking a relaxed environment with local amenities.

Further south, the Cougar Ridge area presents a more contemporary residential option. Properties in Cougar Ridge are a short drive from Winsport, providing modern homes and convenient access to major routes that lead to other Calgary attractions. This area is well-suited for families or those looking for newer holiday rentals.

The Aspen Woods neighbourhood, to the southwest, offers upscale holiday rentals in a picturesque setting. These properties are a short drive from Winsport and provide a tranquil escape with beautiful views and proximity to various shops and services.
What is the cheapest month to stay near Winsport?
The cheapest time to find holiday rentals near Winsport is typically during late Autumn (November) and late Winter (February). November frequently offers the best deals on cabins and homes, often providing lower rates before the peak winter sports season. February can also present various savings once the initial holiday rush has subsided. Guests can often find better deals on properties during these months.
Are there any lakefront holiday rentals near Winsport
Lakefront holiday rentals near Winsport are available, primarily found along the scenic shores of Chestermere Lake and Ghost Lake. These properties are a short drive from Winsport, offering convenient access to water activities such as kayaking, fishing, or simply relaxing by the shore.

These homes often feature spacious decks, fire pits, hot tubs, and full kitchens, making them ideal for families and larger groups.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Stayz customer service and Stayz™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare customer service is available 24/7 to support you every step of the way.

Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.