Curated For You
Weatherhead Family - Ski Season Properties
High End Ski Season Properties
Curated For You
High End Ski Season Properties
chalet
5
Beds
3
Baths
10
Guests
Welcome to the Chamonix Crescent Ski Club Retreat — a beautifully appointed seasonal residence ideally located steps from premier ski clubs and trails in The Blue Mountains. This refined home combines modern comfort, effortless access to winter recreation, and relaxed seasonal living — making it a perfect base for ski season, summer stays, and four-season escapes. Inside, the open-concept living space is bright, inviting, and designed for comfortable gatherings after a day on the slopes. The well-appointed kitchen flows into the dining and living areas, creating an ideal setting for après-ski dinners, cozy movie nights, or morning coffees. Thoughtfully laid-out bedrooms provide privacy and comfort for families, groups, or professionals seeking extended seasonal stays. Step outside to your private hot tub — a standout feature that elevates your seasonal experience year-round. Whether you’re soaking sore muscles after a day on the lifts or enjoying a starlit evening in cooler months, the hot tub adds a resort-style touch to everyday living. Located within walking distance of multiple Blue Mountain area ski clubs and Nordic trails, this property places you in the heart of winter recreation. First tracks and après-ski scenes are just minutes away, while warmer seasons transform the region into a playground for hiking, mountain biking, golf, kayaking, and beach days along Georgian Bay. Positioned close to Blue Mountain Village, Craigleith Ski Club, Alpine Ski Club and Georgian Peaks and steps to the scenic Georgian Trail, this home embodies the Seasonal Properties philosophy — curated homes in extraordinary locations where guests live like locals and embrace year-round adventure. From powder days and summer festivals to lakeside sunsets and fall colours, Chamonix Crescent Ski Club Retreat supports every season with style, comfort, and convenience.
$12,000/month
house
4
Baths
8
Guests
Experience the pinnacle of ski season living in this extraordinary luxury estate perched high above Georgian Bay. Located within the prestigious Georgian Bay Golf Club community, this custom-designed home offers awe-inspiring views of the Georgian Peaks Ski Club and unmatched proximity to Osler Bluff, Craigleith, Alpine, and Georgian Peaks. Inside, no detail has been spared. The gourmet kitchen is a culinary masterpiece with top-of-the-line appliances and a spacious layout perfect for entertaining. A grand living area with a cozy fireplace and heated floors throughout creates a warm retreat after exhilarating days on the slopes. Entertainment abounds with a state-of-the-art home theatre, indoor golf hitting range, poker games room, and ping pong area—making this home an entertainer’s paradise. The lower level is designed for endless recreation, while the main living spaces combine elegance and comfort in equal measure. With five spacious bedrooms and refined finishes, the property is ideal for a professional family or group seeking the ultimate seasonal retreat. The daily snow-cleared driveway ensures convenience, while flexible ownership and thoughtful amenities guarantee a seamless and luxurious experience. Perfectly blending sophistication, comfort, and breathtaking natural beauty, this Georgian Bay estate is more than a rental—it’s a lifestyle. Create unforgettable memories this ski season in a one-of-a-kind home where elegance and adventure meet.
$60,000/season
chalet
4
Beds
3
Baths
8
Guests
$47,000/season
chalet
3
Beds
3
Baths
6
Guests
$35,000/season
Experience elevated mountain living in this gated, luxury chalet at the base of the escarpment—steps to Alpine Ski Club and moments from Craigleith, Georgian Peaks, and Osler Bluff. Designed for discerning families and groups, the residence showcases unobstructed panoramic views of Georgian Bay and Christian Island, with Alpine’s Crescendo run as your dramatic backdrop. Inside, four exquisitely appointed bedrooms with king and queen beds ensure restful nights, while spa-like bathrooms and high-end finishes add hotel-level comfort. Entertain in style in the dedicated sports/media lounge, or host intimate tastings in the statement wine cellar inspired by mid-century craftsmanship. A bonus room provides flexible space for guests or family helpers, and a chef’s kitchen with premium appliances makes après-ski dinners effortless. Outdoors, the escarpment’s snow-kissed scenery sets the scene for memorable days on the slopes and serene evenings at home. With top clubs, snowshoe and hiking trails, and the Village’s dining and boutiques close by, this property blends privacy, convenience, and sophistication. Perfect for families seeking an opulent base for four-season adventure, this chalet delivers unmatched views, thoughtful amenities, and timeless style. Inquire now to make this your private mountain retreat.
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.