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.
$35,000/season
chalet
7
Beds
7
Baths
14
Guests
$60,000/season
chalet
4
Beds
4
Baths
8
Guests
$12,000/month
apartment
3
Beds
2
Baths
6
$22,000/season
chalet
4
Beds
4
Baths
8
Guests
$25,000/season
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.
Collingwoodlands Ski Season Homestead | A Family Retreat Near Osler Bluff Welcome to Collingwoodlands Ski Season Homestead, a warm and inviting family retreat tucked into one of the most desirable recreational communities in the Southern Georgian Bay area. Surrounded by mature trees and the natural beauty of the Niagara Escarpment, this spacious seasonal home offers the perfect setting for families looking to spend an unforgettable winter in The Blue Mountains. With generous accommodations, plenty of room to gather and an exceptional location close to Osler Bluff Ski Club, OslerBrook Golf & Country Club, Blue Mountain Village and downtown Collingwood, this is a property designed for much more than the occasional weekend away. It's a place to settle in, unpack and make The Blue Mountains home for the season. A fantastic Location for an Osler Bluff Family. Location is one of the biggest advantages of Collingwoodlands. The community sits just minutes from Osler Bluff Ski Club, making this an outstanding seasonal home base for Osler families who want to maximize their time on the mountain. Forget loading the vehicle for a long drive to the hill every morning. Have breakfast at home, get everyone into their ski gear and be at the club in minutes. That proximity also creates flexibility throughout the day. Head home for lunch, bring younger children back for a break, or return to the chalet before meeting friends again later in the afternoon. Blue Mountain Resort and Village are also nearby, providing even more skiing, dining, shopping and entertainment throughout the winter. Plenty of Space for Family & Friends A great ski-season property needs to work as a home—not simply as weekend accommodation. Collingwoodlands Ski Season Homestead provides the space families need to comfortably settle in for an extended stay. The home's generous bedroom configuration provides plenty of room for parents, children and visiting family and friends, while multiple living spaces allow everyone to spread out after an active day outdoors. Spend the evening gathered together over dinner, relax with a movie, play games with the kids or simply enjoy a quiet night at home before another day on the mountain. It's the type of property that makes inviting friends and extended family for a ski weekend easy. A True Ski-Country Atmosphere. There is something different about spending an entire winter in The Blue Mountains rather than simply visiting for weekends. Skis can stay here. Winter gear stays here. The kids establish their routines and friendships. Friday afternoon becomes an arrival home rather than the beginning of another vacation. And Saturday morning starts with checking the snow conditions instead of unpacking the car. Collingwoodlands offers exactly that kind of experience—a quiet, established neighbourhood surrounded by nature but close to everything that makes Southern Georgian Bay such an exceptional recreational destination. Après-Ski at Home After the lifts close, return home and enjoy the quieter side of ski-season living. Gather around with family and friends, prepare dinner together and settle in for a relaxed evening after a full day outdoors. Some of the best memories of ski season happen during these moments: children recounting their favourite runs, friends dropping by after skiing, long dinners around the table and evenings that don't need an itinerary. Having a spacious private home allows everyone to enjoy the season at their own pace. More Than a Winter Destination Although this property is particularly well suited to ski season, Collingwoodlands sits in the heart of one of Ontario's great four-season recreational destinations. When the snow disappears, the skis are replaced by golf clubs, bicycles and hiking shoes. OslerBrook Golf & Country Club is nearby, while the broader Southern Georgian Bay region offers outstanding golf, cycling, hiking and mountain biking. Georgian Bay provides endless summer opportunities for swimming, boating, paddleboarding and waterfront adventures, while the Niagara Escarpment offers some of Ontario's most spectacular trails and scenery. Nearby Collingwood provides restaurants, cafés, shops, grocery stores and everyday conveniences, while Blue Mountain Village and Thornbury offer even more opportunities for dining, entertainment and exploring. Collingwoodlands Ski Season Homestead offers families the opportunity to experience The Blue Mountains as locals do—not for a weekend, but for an entire season. Whether your days are spent skiing Osler Bluff, exploring Blue Mountain, enjoying Georgian Bay or simply relaxing together at home, this is a wonderful place to create the traditions and memories that make a ski season special.
Guests
Welcome to Lighthouse Point Penthouse, a spacious three-bedroom seasonal retreat offering spectacular Georgian Bay views, exceptional recreational amenities, and one of Collingwood's most desirable four-season locations. Located at 481 Mariners Way in the sought-after waterfront community of Lighthouse Point, this bright upper-level corner residence offers more than 1,700 square feet of comfortable living space, three bedrooms, two full bathrooms, garage access, and something particularly special for families: an outstanding recreation centre just steps from your door. Whether you're looking for a home for the ski season, an extended summer escape, or several months enjoying everything Southern Georgian Bay has to offer, this is a property where the entire family can settle in and enjoy the season. Wake Up to Georgian Bay One of the defining features of this residence is the view. Expansive windows and the elevated third-floor position provide beautiful, unobstructed views across Georgian Bay while filling the home with natural light. The spacious Great Room creates a natural gathering place for family and friends, complete with a gas fireplace that's particularly welcoming after a winter day on the slopes. The adjoining dining area and fully equipped kitchen make the space equally suited to quiet family evenings or entertaining friends throughout the season. Morning coffee overlooking the Bay, afternoons exploring Collingwood and evenings gathered around the fireplace—this is the relaxed Georgian Bay lifestyle people come here to experience. Three Bedrooms with Room for the Family With three comfortable bedrooms and two full bathrooms, the residence provides plenty of room for families spending an extended season in Collingwood. The primary bedroom features a king bed, ensuite bathroom and beautiful views of Georgian Bay, creating a peaceful retreat at the end of the day. Two additional bedrooms provide flexible accommodation for children, family members or visiting guests. With more than 1,700 square feet of living space, this isn't a compact weekend condo. There is room to unpack, establish a routine and genuinely make the property your home for the season. An Incredible Recreation Centre Steps Away One of the biggest advantages of staying at Lighthouse Point is everything available without having to leave the community. The recreation centre is just steps from the residence and offers an impressive collection of amenities for both adults and children. Enjoy the indoor swimming pool, relax in the hot tubs, warm up in the saunas, or fit in a workout at the fitness centre. For families, the games and recreation spaces provide another place for children to have fun when they're not skiing, swimming or exploring outside. It's particularly valuable during the winter. After a full day skiing, come home, put away the equipment and walk over for a swim, hot tub or sauna before dinner. During the summer, Lighthouse Point's waterfront setting and additional outdoor recreational amenities create an entirely different experience, making this a property that works exceptionally well throughout all four seasons. A Fantastic Home Base for Ski Season For ski families, Lighthouse Point offers a great combination of recreation and location. Blue Mountain Resort is just a short drive away, while the area's private ski clubs—including Craigleith, Alpine, Georgian Peaks and Osler Bluff—are all easily accessible. The residence also includes garage access and exterior ski storage, two features that become especially valuable when you're living in the area for an entire winter. Leave the skis here. Keep the winter equipment organized. Park out of the snow. Instead of packing the family up every weekend, arrive and immediately feel at home. Summer on Georgian Bay When winter ends, Lighthouse Point becomes one of Collingwood's great summer destinations. The waterfront setting places Georgian Bay right outside your door, while Collingwood's extensive trail system makes it easy to walk, run and cycle throughout the area. Spend mornings on the Bay, afternoons golfing, swimming or exploring the trails, and evenings enjoying Collingwood's restaurants and patios. Blue Mountain Village, downtown Collingwood and the Georgian Trail are all nearby, while Thornbury and the rest of The Blue Mountains are an easy drive for another day of exploring. Convenience for an Extended Stay Seasonal living should be comfortable, and 481 Mariners Way offers the practical features that make a longer stay considerably easier. Also note, the Lighthouse Point community is monitored by on-site security 24/7. The building has an elevator, the residence has in-suite laundry, garage access is included, and dedicated exterior ski storage helps keep recreational equipment organized and out of the living space. Combine those conveniences with three bedrooms, generous living areas and the recreation centre next door, and this becomes an exceptionally easy property for families to enjoy for several months at a time. Your Lighthouse Point Home for the Season What makes this property special isn't any single feature—it's how everything comes together. Wake up to Georgian Bay. Spend the day skiing Blue Mountain or one of the area's private clubs. Come home and take the kids swimming. Relax in the hot tub or sauna. Then walk back to your residence, light the fireplace and enjoy dinner overlooking the Bay. In summer, replace ski days with swimming, cycling, golf and afternoons by the water. Lighthouse Point Penthouse at 481 Mariners Way offers the space of a true seasonal home with the amenities of a private resort—all in one of Collingwood's most established waterfront communities. For families looking to experience Collingwood and The Blue Mountains for a month, a season, or longer, this is an exceptional place to call home.
Welcome to Windfall Mountain Retreat, an exceptional seasonal rental located within one of the Blue Mountains' most prestigious four-season communities. Beautifully furnished and thoughtfully designed, this 4-bedroom, 4-bathroom luxury home offers the perfect combination of mountain elegance, modern comfort, and resort-style amenities. Located just a short walk from Blue Mountain Village and the chairlifts, this home allows families to enjoy everything the region has to offer while returning each evening to the privacy and tranquility of one of the area's most desirable neighbourhoods. Thoughtfully Designed for Extended Seasonal Living Offering over 2,500 square feet of beautifully finished living space, this turnkey home has been carefully designed for families looking to enjoy the Blue Mountains for weeks or months at a time. The open-concept main floor features: Bright living room centred around a cozy gas fireplace Gourmet kitchen with granite countertops and premium appliances Spacious dining area ideal for entertaining Convenient main-floor laundry Elegant finishes throughout Large windows frame beautiful mountain views while filling the home with natural light, creating an inviting atmosphere throughout every season. Comfort for Family & Guests The home comfortably accommodates families and visiting guests with: Four spacious bedrooms Four beautifully finished bathrooms Custom built-in closets throughout Luxurious primary suite featuring: Spa-inspired ensuite Freestanding soaker tub Double vanity Frameless glass shower The fully finished lower level adds another generous family room, additional bedroom, and full bathroom, providing excellent separation for children, guests, or extended family. Exclusive Access to The Shed One of Windfall's signature features is The Shed, an exclusive private recreation centre available to residents and guests. Enjoy access to: Heated year-round outdoor swimming pool Scandinavian-inspired sauna Modern fitness studio Outdoor fireplace and lounge area BBQ patio Community gathering spaces Children's play field Whether you're starting your morning with a workout or relaxing after a day on the slopes, The Shed elevates every aspect of your seasonal stay. A Four-Season Lifestyle Like No Other Windfall offers immediate access to the very best of the Blue Mountains. Within minutes you'll find: Blue Mountain Village Blue Mountain ski lifts Monterra Golf Scenic hiking and biking trails Scandinave Spa Georgian Bay beaches Downtown Collingwood Thornbury's boutiques, cafés, and restaurants Whether you're enjoying fresh powder in January, golfing championship fairways in July, or hiking colourful trails in October, every season brings something extraordinary. The Perfect Home for Seasonal Living Windfall Mountain Retreat is ideal for: Ski season families Executive relocations Remote professionals Summer golf vacations Families exploring the Blue Mountains before purchasing Fully furnished and move-in ready, this home allows you to settle in immediately and enjoy everything the region has to offer.