Curated For You
Available for 2026-2027
What is Still Remaining for This Coming Season
Curated For You
What is Still Remaining for This Coming Season
chalet
3
Beds
3
Baths
6
Guests
Welcome to Top of Oslerbluff, a beautifully renovated private ski-season retreat set on more than an acre in The Blue Mountains and just minutes from Osler Bluff Ski Club. Designed for families who want to fully settle into the winter season, this magnificent chalet that offers the space, privacy and warmth that make a true ski-season property special. The open-concept main level features vaulted ceilings, exposed wood beams, hardwood floors and a dramatic floor-to-ceiling stone wood-burning fireplace — the perfect place to gather after a full day on the slopes. The renovated chef’s kitchen includes premium appliances, Cambria countertops and a large island ideal for family breakfasts, après-ski dinners and entertaining throughout the winter. The main-floor primary suite provides a comfortable private retreat, while the finished walkout lower level includes two additional bedrooms, a full bathroom, expansive recreation room and bar, giving children and guests their own space to relax after skiing. A three-car insulated garage provides plenty of room for vehicles, skis and winter equipment, while the large stone firepit and private wooded setting create a true mountain-home atmosphere. For an Osler family, this is the kind of property that allows you to stop commuting north every weekend and simply live the ski season — wake up close to the club, ski throughout the day, return home to a real wood fire and enjoy the winter with family and friends. Available for Full Ski Season Top of Oslerbluff is an ideal home base for a family looking to make the most of an entire winter in The Blue Mountains.
$44,000/season
chalet
4
Beds
3
Baths
6
Guests
$32,000/season
chalet
5
Beds
4
Baths
10
Guests
$40,000/season
chalet
3
Beds
2
Baths
6
Guests
$15,000/season
chalet
7
Beds
4
Baths
14
Guests
$60,000/season
Welcome to 2 Evergreen Road, a beautifully appointed executive bungalow offering the perfect combination of privacy, space and access to the very best of Southern Georgian Bay. Set on approximately one acre of mature, park-like grounds, this exceptional 4-bedroom, 3-bathroom home provides more than 2,500 square feet of thoughtfully designed, single-level living. Located just minutes from Blue Mountain Village, skiing, golf, trails, beaches and downtown Collingwood, it is an ideal home for families seeking to settle into the region for a month, season or extended stay. Whether you're spending the winter skiing, escaping the city for summer, or simply looking for a peaceful home base near Georgian Bay, Evergreen Mountain Retreat offers a true four-season lifestyle. One of the home's greatest features is its spacious bungalow design. With the principal living spaces and all four bedrooms located on one level, the home feels open, comfortable and effortless for extended seasonal living. A garage for parking and entry to the home for ski season guests. The impressive Great Room features soaring vaulted ceilings, hardwood floors, oversized windows and a gas fireplace, creating a warm gathering place for family and friends. Ten-foot ceilings throughout much of the remainder of the home add to the sense of space, while radiant in-floor heating provides exceptional comfort during the colder months. It's equally suited to quiet family evenings after skiing and entertaining friends throughout the season. A Chef's Kitchen Made for Entertaining. At the centre of the home is a beautifully designed gourmet kitchen with stainless steel appliances, quartz and wood countertops, generous cabinetry, a bar fridge and ample preparation space. The kitchen connects naturally with the home's dining and living areas, making it ideal for everything from relaxed family breakfasts before heading to the mountain to larger dinners with friends. For guests spending several months in the Blue Mountains, this is a home that functions as a genuine residence rather than simply a place to stay. Four Bedrooms for Family & Guests. The home offers four spacious bedrooms and three bathrooms, providing excellent flexibility for families, visiting friends and extended seasonal stays. The primary suite is a private retreat with its own ensuite and direct walkout to the expansive rear deck, allowing the home's peaceful outdoor setting to become part of everyday living. One of the additional bedrooms can also function beautifully as an office or den, creating an ideal setup for professionals who want to work remotely while spending a season in the Blue Mountains. Surrounded by mature landscaping, the expansive backyard provides remarkable privacy and plenty of space to enjoy the outdoors throughout the year. It is a setting that allows you to enjoy the Blue Mountains lifestyle without sacrificing privacy or space. Perfect for the Winter Ski Season. Evergreen Mountain Retreat is exceptionally well positioned for families spending the winter in the area. Blue Mountain Village and the ski hills are only minutes away, while the region's private ski clubs — including Osler Bluff, Craigleith, Alpine and Georgian Peaks — are easily accessible.Radiant heated floors, a gas fireplace and the private outdoor hot tub make returning home after a day on the slopes almost as enjoyable as the skiing itself. You're close enough to enjoy everything happening at Blue Mountain and downtown Collingwood, yet far enough removed to return home to a quiet, private residential setting. Nearby you'll find: Blue Mountain Village and ski hills Private ski clubs Golf courses Scandinave Spa Georgian Bay beaches Hiking and cycling trails Downtown Collingwood restaurants and shops Thornbury and the wider Blue Mountains region This central location makes 2 Evergreen Road an outstanding home base for exploring Southern Georgian Bay throughout all four seasons. A True Home Away from Home Flexible Monthly & Seasonal Availability Available for monthly and extended seasonal rentals of 30+ days. Whether you're searching for a winter ski season home, a summer escape near Georgian Bay, or a peaceful extended stay close to Collingwood and Blue Mountain, Evergreen Mountain Retreat offers the space, privacy and location to make the region feel like home. Pets considered. Inquire today with Seasonal Properties to experience four-season living at 2 Evergreen Road.
117 Millennium Way is perfectly suited to families seeking a comfortable, beautifully finished chalet close to Craigleith Ski Club. From the warmth of the stone fireplace to the mountain views and walk-to-club convenience, every aspect of the home supports the rhythm of an unforgettable winter season. Whether enjoying quiet evenings together, welcoming friends for a ski weekend, or establishing new family traditions, this Orchard chalet offers the space and location to make the most of winter in the Blue Mountains. Featuring four bedrooms plus an additional lower-level bedroom, four bathrooms, and approximately 3000+ square feet of living space, the home combines classic chalet character with thoughtful modern upgrades. Best of all, Craigleith Ski Club is within walking distance, allowing your family to enjoy the mountain lifestyle without relying on the car for every ski day. Let's chat about your seasonal fun on Millennium Way before it is too late!
Welcome to Brophy’s Lane Beach & Ski Retreat, a charming four-season escape tucked away on a private, mature treed property in The Blue Mountains. This fully furnished three-bedroom, two-bathroom bungalow offers the perfect combination of privacy, comfort, and location. Best of all, you're just a two-minute walk from a quiet sandy beach on Georgian Bay, while Blue Mountain Resort and the area's private ski clubs are only minutes away. Inside, the home features a warm and inviting living area with a gas fireplace, an eat-in kitchen, and a bright four-season sunroom overlooking the surrounding trees. The comfortable single-level layout makes it ideal for families looking to settle in for a month, an entire season, or longer. Outside, enjoy the spacious property, patio, and firepit—perfect for summer evenings after a day on Georgian Bay. Additional outdoor storage provides plenty of room for skis, bikes, paddleboards, and all the equipment that comes with enjoying life in Southern Georgian Bay. A True Four-Season Location During the winter, Craigleith Ski Club, Alpine Ski Club, Georgian Peaks, and Blue Mountain Resort are all within easy reach, making this an excellent home base for ski season. In the warmer months, walk down the road for a swim in Georgian Bay, explore nearby cycling and hiking trails, play one of the area's many golf courses, or spend the afternoon in Collingwood, Blue Mountain Village, or Thornbury. Brophy’s Lane Beach & Ski Retreat offers something special in every season—walk-to-water access, privacy, and the mountains just minutes away. Whether you're looking for a summer by Georgian Bay or a home for the ski season, this is an ideal property for experiencing The Blue Mountains like a local.
Welcome to Windrose Valley Boulevard, an exceptional luxury estate tucked into the exclusive Windrose Valley community at the base of the Niagara Escarpment. Set on approximately 2.3 private acres, this impressive home offers around 5,000 square feet of beautifully designed living space, combining the character of a mountain retreat with the scale and amenities of a true luxury residence. With six bedrooms and five bathrooms, expansive gathering spaces and remarkable proximity to the region's ski clubs, trails, golf courses and Georgian Bay, Windrose Valley Estate is ideally suited to families looking to settle into the Blue Mountains lifestyle for a month, season or extended stay. Designed for Families to Gather Step inside to an impressive open-concept interior defined by cathedral ceilings, warm wood posts, oversized windows and abundant natural light. At the heart of the home is a generous great room anchored by a gas fireplace — the perfect gathering place after a winter day on the slopes or a summer afternoon exploring the Escarpment. Multiple walkouts connect the interior with decks and balconies, while the home's spacious layout gives family and guests plenty of room to come together without sacrificing privacy. A Kitchen Made for Entertaining The expansive kitchen is designed for both everyday family living and entertaining, with a large centre island and bar seating complemented by a generous breakfast area. A separate formal dining space provides another setting for memorable dinners, holiday gatherings and evenings with friends. For families staying for several months rather than several nights, this is an important distinction: Windrose Valley Estate feels and functions like a home, allowing guests to truly settle into the region. Six Bedrooms for Family & Guests With five above-grade bedrooms plus an additional bedroom on the finished lower level, the home provides exceptional flexibility for larger families, multi-generational stays and visiting guests. Four bedrooms are located on the upper level, including a spacious primary bedroom with ensuite. A main-floor bedroom can also provide flexible accommodation or function as an office for those combining seasonal living with remote work. The additional lower-level bedroom and bathroom create further separation and privacy for guests. Your Own Private Après-Ski Retreat The finished lower level transforms the home into an exceptional year-round recreational retreat. Enjoy a spacious family and games room, private gym, sauna, wine cellar and additional living space — creating the perfect environment to unwind without leaving home. During ski season, return from the mountain for a sauna and a relaxed evening with family. During the warmer months, start the morning in the gym before heading out for golf, cycling or hiking. These are the features that make an extended stay at Windrose Valley feel truly special. 2.3 Acres Beneath the Escarpment One of the property's greatest luxuries is its setting. A long driveway leads into approximately 2.3 acres of private grounds, providing space and separation while maintaining remarkable proximity to the area's major attractions. Views toward the Niagara Escarpment reinforce the property's mountain-estate atmosphere, while decks and balconies create natural extensions of the home's living spaces throughout the warmer seasons. It is a peaceful country setting without sacrificing access to everything the Blue Mountains has to offer. Osler Bluff Ski Club is approximately five minutes away, while Blue Mountain is also approximately five minutes from the property. That means mornings can be spent on the slopes without the long drive typically associated with a country estate. Come home for lunch, enjoy the sauna after skiing, entertain friends for dinner and settle into the rhythm of an entire winter in the mountains. Despite its private setting, the property is approximately 10 minutes from historic downtown Collingwood, putting restaurants, cafés, boutiques, groceries and everyday conveniences within easy reach. Throughout the warmer months, the surrounding region opens up to golf, hiking, cycling, Georgian Bay beaches and waterfront activities. Thornbury, Blue Mountain Village and the region's private ski and golf clubs are all easily accessible, making this an outstanding base for experiencing Southern Georgian Bay throughout the year. A True Four-Season Lifestyle Property Windrose Valley Estate is ideally suited to guests seeking more than a traditional vacation rental. It is a home for families who want to live in the Blue Mountains for a season — keeping their ski equipment ready throughout winter, establishing a summer base near Georgian Bay, working remotely from the Escarpment or spending several months exploring the region before purchasing a home of their own. Whether your days revolve around skiing, golf, cycling, hiking, entertaining or simply enjoying the privacy of a beautiful country estate, this property provides the space and location to make the most of them. Flexible Monthly & Seasonal Availability Available for monthly and extended seasonal rentals of 30+ days. Ideal for winter ski season, summer and fall stays, executive relocations and extended four-season living. Inquire today to experience Windrose Valley Estate — where 2.3 private acres, luxury amenities and exceptional access to Osler Bluff and Blue Mountain come together in one remarkable seasonal home.