Wintergreen holiday rentals

We found 30 holiday rentals — enter your dates for availability

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit Wintergreen

  • Outdoor Activities: Enjoy skiing, hiking, and beautiful beaches amidst stunning landscapes.
  • Charming Accommodation: Choose from cosy condos, private homes, and delightful cottages for a relaxing stay.
  • Golfing Paradise: Play on breathtaking golf courses perfect for couples and families alike.
  • Cultural Exploration: Discover nearby towns with a laid-back atmosphere and local charm.
  • Adventure and Relaxation: Experience a unique blend of thrilling activities and serene retreats in nature.

Popular types of accommodation around Wintergreen

If you're pondering the ideal accommodation for your getaway in Wintergreen, look no further! Our most sought-after options include cosy condos, charming houses, and delightful cottages. Whether you're after a wintergreen rental, a holiday home at Wintergreen Resort, or a snug condominium, we have an array of vacation rentals to suit your needs. Enjoy your stay with confidence, knowing we prioritise transparency and value.

  • Condos: The top choice for holidaymakers in Wintergreen, offering modern amenities and a convenient location for your stay.
  • Houses: A popular option for families or groups seeking spacious accommodations and a home-like atmosphere.
  • Cottages: A charming retreat that provides a cosy and rustic experience, perfect for a peaceful getaway.
  • Apartments: Ideal for couples or solo travellers, these self-contained spaces offer comfort and flexibility.
  • Chalets: A delightful choice for those who want a mountain retreat with character and stunning views.**

Top attractions near Wintergreen

Wintergreen, nestled in The Blue Mountains of Ontario, offers a delightful mix of outdoor activities and cultural experiences. Visitors can enjoy beautiful beaches, explore marinas, and hit the ski hills for some thrilling winter sports. With picturesque landscapes surrounding you, it's an ideal spot for families, groups, or solo travellers seeking adventure and relaxation in nature's embrace.

  • Blue Mountain Ski Resort: A premier ski destination, offering thrilling slopes and adventure activities. Enjoy the vibrant outdoor atmosphere, perfect for snow enthusiasts and families alike.
  • Collingwood Scenic Caves: A family-friendly park featuring stunning caves and eco-friendly trails. Explore nature while soaking in breathtaking views, ideal for outdoor lovers.
  • Blue Mountain Beach: A picturesque beach with serene vibes, perfect for relaxation and water activities. Enjoy the sun, sand, and stunning views of the surrounding area.

Things to do recommended for couples

Ready for a romantic getaway in Wintergreen? Hit the slopes at Blue Mountain Ski Resort for some thrilling skiing, unwind at the serene Scandinave Spa, or enjoy a wine tasting at Georgian Hills Vineyards—perfect for a lovely afternoon together amidst beautiful scenery.

Things to do recommended for families

Families can splash around at the Plunge Aquatic Centre, located 644m from Wintergreen. This aquatic venue is perfect for kids, offering a range of fun water activities and a vibrant atmosphere that ensures a fantastic day out for the whole family.

Things to do recommended for groups

Enjoy a round of golf at Cranberry Resort Golf Course or Collingwood Golf Course, both offering stunning outdoor vibes just a short drive from Wintergreen. For an adrenaline rush, embark on an adventure at Scenic Caves Nature Adventures with ziplining amidst breathtaking scenery.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking with Stayz is a breeze

Are you aiming to save on your upcoming adventure? Being flexible with your travel dates can make a difference, as prices can fluctuate. You might also enjoy substantial savings by opting for a longer stay. To discover a Stayz property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Where to stay near Wintergreen

Wintergreen, nestled in The Blue Mountains of Ontario, offers a delightful mix of relaxation and adventure. With stunning golf courses and breathtaking views, it's perfect for couples seeking a romantic getaway or families looking for fun. Explore nearby towns and enjoy the laid-back atmosphere, where recreation meets budget-friendly options. Whether you're after scenic hikes or cozy retreats, Wintergreen promises an unforgettable experience for every traveller.

  • Collingwood: Located a mere 8.0km from Wintergreen, Collingwood is an adventure-seeker’s paradise. This vibrant city is renowned for its outdoor pursuits, especially skiing, making it a popular destination during the winter months. With numerous ski resorts nearby, visitors can enjoy exhilarating slopes and stunning views. Beyond skiing, Collingwood offers a range of body treatments for those looking to unwind after a day of adventure. The scenic beauty of the area is complemented by local landmarks such as the picturesque lake and charming beaches, perfect for a relaxing day out.
  • The Blue Mountains: The Blue Mountains is a stunning region where Wintergreen resides and is celebrated for its outdoor adventures. This city attracts thrill-seekers with its excellent ski facilities and breathtaking landscapes. Here, you can indulge in various activities, from skiing to relaxing body treatments at local wellness centres. The proximity to beautiful lakes and family-friendly beaches adds to its allure, making it an ideal destination for both adventure enthusiasts and families looking for a fun day out.
  • Blue Mountain Village: Just 483m from Wintergreen, Blue Mountain Village epitomises the essence of adventure. This lively hub is perfect for those keen on skiing and enjoying the great outdoors. With its array of ski resorts and leisure facilities, visitors can immerse themselves in the thrill of winter sports. Beyond the slopes, the village is home to a beautiful lake, a lively theme park, and serene parks, providing ample opportunities for relaxation and enjoyment. The vibrant atmosphere makes it a must-visit for anyone looking to experience the best of the Blue Mountains.

Best time to go to Wintergreen

If you're planning a trip to Wintergreen, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like April to May and November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January20.5°F (-6.4°C)Light RainVery CloudyAverageAverage
February20.5°F (-6.4°C)Light RainMostly CloudyAverageSlightly High
March29.3°F (-1.5°C)Light RainMostly CloudyAverageAverage
April39.7°F (4.3°C)Light RainMostly CloudyLowSlightly Low
May52.2°F (11.2°C)Light RainMostly SunnyLowSlightly Low
June60.6°F (15.9°C)Light RainMostly SunnyHighAverage
July67.1°F (19.5°C)Light RainMostly SunnyHighAverage
August66.6°F (19.200000000000003°C)Light RainMostly SunnyHighSlightly High
September60.3°F (15.7°C)Light RainMostly SunnyAverageAverage
October48.7°F (9.3°C)Light RainMostly CloudyAverageAverage
November37.0°F (2.8000000000000003°C)Light RainMostly CloudyLowSlightly Low
December28.2°F (-2.1°C)Light RainMostly CloudyAverageSlightly High

What do I need to keep in mind when booking a vacation around Wintergreen

If you’re travelling with a group, family, pets, or planning for an extended stay, be sure to apply the appropriate filters to meet your needs. Here are some helpful Stayz booking tips for you.

  • Travelling to Wintergreen with a group: Think about how many bedrooms you'll require, along with features like a fully-equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily refine your search for all these options and more on Stayz.
  • Travelling to Wintergreen with young kids: Travelling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, along with suitable facilities like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that are great for families.
  • Taking your pets with you to Wintergreen: For many, a family holiday isn’t truly complete without their furry companion by their side. If this resonates with you, take a look at Stayz properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Wintergreen: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to enhance your search.

Stayz Trips: Planning made easy

Stayz's Trip Board offers a handy area to plan new adventures, resume your previous arrangements, or manage your travel itineraries. You can easily access your saved or booked properties, which are sorted into categories like Potential, Upcoming, or Current Trips. To begin enjoying the benefits of Trip Boards, simply head over to: https://www.stayz.com.au/trips.

**Based on Stayz properties bookings.

Frequently asked questions

What are the best holiday rentals near Wintergreen?
The best holiday rentals near Wintergreen are typically located right in The Blue Mountains, Ontario, Canada, offering direct access to the area's activities. You will find a wide array of choices, from modern condos that provide convenience and comfort to charming chalets great for a mountain getaway. You can choose properties that place you right at the heart of the action. If you are willing to drive a bit further, renting in nearby areas can be an affordable option for finding larger properties.

Many of these properties offer desirable amenities such as a fireplace for cosy evenings, a hot tub for relaxation after a day out, and a deck or patio for enjoying the views. These homes are ideal for families or groups seeking a comfortable and memorable stay.
Are there any cheap holiday rentals near Wintergreen?
There are several affordable holiday rentals near Wintergreen, especially if you are flexible with location and travel dates. Budget-friendly stays are typically around AU$125 per night. Some stays even drop lower in November and April 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, self-parking, and toiletries, and can range from cosy chalets to modest condos, 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 Wintergreen while keeping costs down.

*Pricing data are based on past 12 months data.
What are the top holiday rentals with pools near Wintergreen?
There are over 286 holiday rentals near Wintergreen that offer access to swimming pools, including both private and shared options. These properties are concentrated in areas like The Blue Mountains and surrounding neighbourhoods. Guests can find a variety of rental types, from condos to private holiday houses, many featuring full kitchens, Wi-Fi, and comfortable living spaces, superb for families or groups seeking a memorable stay.

When selecting your ideal rental, consider the benefits of different pool types. Private pools provide seclusion and are excellent for families, while shared pools often include access to additional amenities such as fitness centres. For cooler months, many properties offer heated or indoor pool options, so checking availability based on your travel dates is recommended.
What are the best family holiday rentals near Wintergreen?
There are over 400 family-friendly holiday homes in the broader region surrounding Wintergreen, offering ample space and comfort for groups of all sizes. Many of these properties boast multiple bedrooms and bathrooms, full kitchens, and generous living areas, all designed with families in mind. With such a wide selection, you can find stays with outdoor play areas or yards where kids can play, and washer/dryers to handle laundry during the trip.

When choosing the best fit for your family, focus on properties where adults and kids each have space to unwind, and look for homes with practical utilities like well-equipped kitchens to save on dining out. Staying just a short drive from Wintergreen can mean less travel each day and more time enjoying the surroundings.
Are there any luxury holiday rentals near Wintergreen?
Around Wintergreen, there are several luxury holiday rentals that combine the natural scenery with modern comfort. These properties often feature amenities such as private hot tubs, gourmet kitchens, spa-style bathrooms, and scenic lake or mountain views. Guests can also find properties with private heated pools, private chefs, and premium bedding.

These homes are ideal for families or larger groups, offering conveniences like air conditioning and entertainment spaces. Many of these exceptional properties are managed by highly rated Stayz hosts, ensuring a professional and premium experience.
How much is a holiday rental near Wintergreen?
Holiday rentals near Wintergreen 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$125 per night, providing an affordable option. Mid-range rentals, including private homes, are generally around AU$330 per night, offering more comfort and privacy. Upscale options can cost AU$630 or more per night, especially during peak seasons.

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 Wintergreen?
When visiting Wintergreen, several areas offer excellent holiday rental options. The village at the base of Wintergreen itself is a prime location, providing direct access to the slopes and village amenities. Properties here are great for those who desire convenience and proximity to activities and dining.

For a slightly more secluded experience, the areas just beyond the main village offer a range of properties with stunning mountain views. These homes provide a peaceful retreat while still being a very short drive from Wintergreen's attractions. Access to Wintergreen from these properties is straightforward, making daily excursions simple.
What is the cheapest month to stay near Wintergreen?
The cheapest time to find holiday rentals near Wintergreen is typically during the shoulder seasons (April and November). November is frequently the cheapest month, often providing the best deals on cabins and homes, with rates often 20% less compared to peak season. Guests can often find various savings during these months, along with greater availability.
Are there any lakefront holiday rentals near Wintergreen
Lakefront holiday rentals near Wintergreen offer a great mix of comfort, scenery, and outdoor adventure. Many are located along quiet lakes like Georgian Bay. These properties are a short drive from Wintergreen, offering convenient access to water activities such as kayaking, fishing, swimming, 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. Guests can enjoy mountain and lake views, spot wildlife, and unwind in peaceful surroundings after exploring local trails.
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.

More holiday ideas