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
4
Baths
8
Guests
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.
$12,000/month
chalet
4
Beds
4
Baths
8
Guests
$25,000/season
cottage
2
Beds
2
Baths
4
Guests
$4,500/month
chalet
5
Beds
3
Baths
10
Guests
$12,000/month
chalet
4
Beds
3
Baths
8
Guests
$22,000/season
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.
Tucked into the peaceful countryside of Duntroon Highlands, Escarpment Escape is a refined Scandinavian-inspired retreat designed for those who value simplicity, nature, and elevated seasonal living. Surrounded by trees and rolling escarpment landscapes, this thoughtfully curated two-bedroom residence offers a calm, minimalist aesthetic paired with modern comfort — creating a true sanctuary just minutes from Devil’s Glen and Nordic Highlands. Inside, natural wood finishes, clean architectural lines, and expansive natural light define the space. The open-concept living area invites relaxed mornings with coffee overlooking the forest and cozy evenings by the fire after a day outdoors. Every detail reflects the essence of Nordic design — warm, functional, and intentionally connected to nature — making it an ideal environment for extended seasonal stays or work-from-anywhere escapes. Located within one of the region’s most sought-after four-season landscapes, this home offers seamless access to hiking, cross-country skiing, and golf at nearby Duntroon Highlands, with the vibrant lifestyle of Collingwood and The Blue Mountains only a short drive away. Guests can embrace a slower rhythm here, whether exploring escarpment trails, enjoying Nordic skiing, or simply recharging in a peaceful countryside setting. Escarpment Escape embodies the Seasonal Properties philosophy — curated homes that allow guests to live like locals while experiencing a refined, nature-driven lifestyle. With its Scandinavian warmth, escarpment setting, and proximity to adventure, this residence offers an authentic seasonal chapter rooted in wellness, design, and outdoor connection.
Welcome to the Indian Trail Seasonal Retreat — a beautifully appointed residence nestled in a peaceful enclave of The Blue Mountains, designed for guests seeking balance, comfort, and effortless access to year-round adventure. Set in a serene neighbourhood yet just minutes from Georgian Bay, ski clubs, trails, and village amenities, this home delivers the perfect blend of tranquility and lifestyle convenience. Inside, the open-concept living space creates a welcoming atmosphere filled with natural light and thoughtful design. The well-appointed kitchen flows seamlessly into the dining and living areas — ideal for relaxed mornings, après-ski evenings, and extended seasonal stays with family or friends. Comfortable bedrooms offer privacy and ease, making this home a great choice for seasonal guests, professionals seeking extended stays, or outdoor lovers looking for a base near all of The Blue Mountains’ natural attractions. Seasonal Adventures & Outdoor Access This property’s location opens the door to a wide range of outdoor experiences throughout the year. In winter, enjoy proximity to Blue Mountain Resort, ski clubs, and Nordic trails — where ski season, snowshoeing, and winter festivals become part of everyday life. In the warmer months, explore scenic hiking routes, cycling on the Georgian Trail, afternoons on the beach at Georgian Bay, and world-class golf courses nearby. Tranquil by design yet connected to recreation, Indian Trail Seasonal Retreat offers balance: a peaceful setting for quiet moments and a gateway to abundant activity. Whether it’s morning coffee on the deck, a sunset walk along scenic trails, or a day spent at the slopes followed by a cozy evening indoors, this residence supports the full range of seasonal living experiences. Live Like a Local Indian Trail embodies the Seasonal Properties philosophy — curated homes in prime locations that allow guests to live like locals while enjoying unforgettable seasonal moments. With easy access to Collingwood’s dining, shopping, and four-season events, plus the natural beauty of the escarpment and bay, this home offers elevated lifestyle value in one of Ontario’s most desirable destinations.
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.