Curated For You
Chalet Options Near Osler Bluff Ski Club
Ideal Rentals for Osler Families
Curated For You
Ideal Rentals for Osler Families
chalet
4
Beds
3
Baths
8
Guests
Welcome to this exceptional seasonal home located in the prestigious Swiss Meadows neighbourhood of The Blue Mountains — a community known for its privacy, natural beauty, and close proximity to world-class amenities. Perfectly positioned for guests seeking refined seasonal living, this residence delivers both elegant comfort and effortless access to year-round adventure. Inside, open-concept living spaces create a warm, inviting environment filled with natural light and thoughtful design. The living, dining, and kitchen areas flow seamlessly together, providing an ideal backdrop for entertaining friends and family or simply unwinding after a day of outdoor exploration. Generously proportioned bedrooms and modern amenities make this home equally suited for extended seasonal stays, family vacations, or groups seeking a four-season retreat. Swiss Meadows is one of The Blue Mountains’ most sought-after neighbourhoods — just minutes from Blue Mountain Resort, ski clubs, and Nordic trails, yet tucked into a serene enclave that feels worlds away from everyday life. During ski season, easy access to lifts, après-ski gatherings, and village culture creates an effortless, ski-centric experience. In sunnier months, scenic hiking routes, mountain biking, golf courses, and the sandy shores of Georgian Bay await. Residents and guests in this area enjoy close proximity to the Georgian Trail, Northwinds Beach, and vibrant local dining and shopping options in Collingwood and Blue Mountain Village. Whether you’re seeking ski days in winter or lakeside evenings in summer, this home supports an active, balanced lifestyle in one of Ontario’s most desirable four-season destinations. Swiss Meadows Seasonal Residence embodies the Seasonal Properties philosophy — curated homes in exceptional locations where guests can truly live like locals. With its elegant design, village adjacency, and access to outdoor adventure, this home offers an elevated seasonal experience. Explore ski slopes and chairlift access in winter, mountain trails and golf excursions in warmer months, and charming village life all year round. Here, comfort, convenience, and lifestyle combine to create unforgettable seasonal stays in The Blue Mountains.
$24,000/season
house
4
Beds
3
Baths
10
Guests
$10,000/month
chalet
4
Beds
3
Baths
6
Guests
$32,000/season
chalet
7
Beds
4
Baths
14
Guests
$60,000/season
Make your winter getaway unforgettable in this fabulous Collingwood home with spectacular style. Located just minutes from Collingwood’s downtown core, the perfect location for anyone that wants a quiet retreat minutes from the action. Only a 15-minute drive to Blue Mountain Village, you can enjoy the slopes any day of the week. Access the Georgian Trail through Collingwood or Blue Mountain to take advantage of snowshoeing and cross country skiing all the way to Meaford. You’ll love being near so many trail systems that give you a new view for every outing. When you’re not on an outdoor adventure, make yourself at home and indulge in the surrounding restaurants and amenities with local gyms, yoga studios, fantastic eateries, grocery stores, and boutique shopping. You don’t need to worry about carpooling, as this 2 car garage and 6 car driveway can accommodate friends and family easily. You’re immediately greeted with fantastic Farmhouse interiors that make you feel right at home as you step inside. One floor living is made possible with the primary bedroom and laundry access on the main floor. With an open concept kitchen, dining, and living room, it’s easy to stay connected throughout your stay and enjoy each other's company. Feeling brave? You can use the BBQ on the expanded deck outside in the winter, but you may be more inclined to soak in the hot tub after a day at the slopes. There’s an outdoor fireplace for chilly evenings you’d rather spend under the stars. Upstairs you’ll find a secondary living room, 4 piece bathroom, and a separate living room for additional guests or kids that want their own space. The kitchen looks like it was ordered right out of a magazine with a beautiful island, marble-style backsplash, large countertops, and plenty of cupboard space for storage. When you’re not enjoying one of the many restaurants, you’ll love the convenience of the S/S appliances, including a stove, fridge, microwave, and dishwasher for easy clean-up. You’ll love the hidden barn-door pantry that automatically closes if you’ve left it open while preparing your meal. No need to pack the pots, pans, and cutlery - we provide everything except your coffee, food, and spices. The living room boasts a soaring ceiling with exposed wooden beams, and a brick feature wall, complimenting the modern farmhouse feel. Unwind by the fire and catch up on some Netflix for a quiet night in. With a warm and cozy feel, the furniture was selected with your ultimate comfort in mind. You can easily slip outside for a breath of fresh air with the walk-out patio through the double doors. The primary bedroom is the ultimate place to stay on the main floor, with deck access through your own set of double patio doors, conveniently close to the hot tub. The large ensuite with a walk-in shower and double sinks is tucked away behind a sliding barn door that also leads to the large walk-in closet, where you can unpack and feel right at home. Upstairs, you’ll find two more generously sized bedrooms with their own four-piece bathroom available for slow mornings. Newly renovated 4th bedroom for guests or extended family in the renovated basement lounge area.
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.
Welcome to Windrose Valley Boulevard, an impressive luxury seasonal home set within the exclusive Windrose Valley community at the base of the Niagara Escarpment. Beautifully furnished and filled with natural light, this expansive residence combines the scale of a private country estate with remarkable access to skiing, golf, trails, Blue Mountain Village and downtown Collingwood. Set on an impressive 1.93-acre landscaped property, this substantial 4-bedroom, 7-bathroom luxury home has been designed for families who appreciate space, privacy, entertaining and the opportunity to enjoy the Blue Mountains lifestyle for an entire season. An Impressive Home Designed for Gathering. From the moment you enter, the scale and natural light of the home create a wonderful sense of arrival. The open-concept main floor is highlighted by soaring cathedral ceilings and dramatic floor-to-ceiling windows, bringing the surrounding Escarpment landscape into the home. At the heart of the main level is a spacious great room anchored by a gas fireplace — an inviting place to gather after a winter day on the slopes. A grand piano adds another distinctive touch, while the generous layout provides plenty of room for family and friends to enjoy the home together without feeling crowded. A Gourmet Kitchen for Family & Entertaining The oversized gourmet kitchen is designed for a home of this scale and flows naturally into an expansive dining area. Generous Accommodations for Family & Guests. The home's substantial bedroom configuration provides excellent flexibility for larger families, visiting friends and multi-generational stays. A bedroom on the main level provides convenient additional accommodation, while the upper floor includes the impressive primary suite and additional bedrooms. Several of the upper bedrooms feature their own ensuite bathrooms, providing a wonderful level of privacy for family and guests. The primary suite is particularly impressive, with beautiful views toward the Escarpment, a luxurious 5-piece ensuite and the added convenience of its own ensuite laundry. Your Own Private Entertainment Level When the skiing ends, the fun doesn't have to. The finished lower level has been designed as a dedicated family entertainment area and includes: Ping pong Air hockey Card and games area Built-in sound system Large family and recreation space It's an ideal setup for children and teenagers while allowing the adults to enjoy the quieter spaces throughout the rest of the home. For a family spending an entire ski season together, having multiple recreational and gathering areas makes this property particularly special. Private Hot Tub & Outdoor Living Step outside and the Windrose Valley lifestyle continues. Set on approximately two acres, the property offers plenty of space to enjoy the outdoors while maintaining the privacy of a country estate. During the warmer months, the property transforms into an exceptional base for outdoor dining, entertaining, golf, cycling and exploring the Blue Mountains. An Exceptional Blue Mountain Ski Season Location. The location is one of the property's greatest advantages. Windrose Valley sits at the base of the Escarpment, only a few minutes from Blue Mountain Village and the ski hills. The region's private ski clubs are also within easy reach, making the property an excellent seasonal base for families skiing at Blue Mountain, Osler Bluff or elsewhere throughout the area. The large property, outdoor entertaining areas and mountain setting make it an outstanding home base for enjoying Southern Georgian Bay throughout the seasons. Made for Extended Seasonal Living 12 Windrose Valley Boulevard is ideally suited to families looking for something beyond a weekend getaway. It is a home where you can unpack, settle in and establish your own routine in the Blue Mountains. Ideal for: Full winter ski seasons Extended summer and fall stays Larger and multi-generational families Executive and corporate relocations Families building or renovating locally Guests exploring the area before purchasing a home The scale, amenities and location allow the property to function beautifully as a genuine seasonal residence. Flexible Monthly & Seasonal Availability Available for monthly and extended seasonal rentals of 30+ days. Whether you're looking for an exceptional winter ski home or a private four-season retreat close to Blue Mountain and Collingwood, 12 Windrose Valley Boulevard offers the space, amenities and setting for an unforgettable extended stay. Inquire today with Seasonal Properties and experience luxury mountain living in Windrose Valley.
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.