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
house
3
Beds
2
Baths
5
Guests
Welcome to Sunset Point Retreat, a beautifully appointed four-season home that perfectly captures the relaxed lifestyle of Collingwood and Southern Georgian Bay. Nestled in one of the town's most desirable neighbourhoods, this charming retreat offers the rare opportunity to enjoy the best of waterfront living, vibrant downtown amenities, and world-class recreation—all within minutes of your front door. Located just steps from Sunset Point Park and the shores of Georgian Bay, this inviting home is equally suited for summer adventures, colourful autumn escapes, and unforgettable winter ski seasons. Blue Mountain Resort is only a short drive away, while Collingwood's historic downtown is within easy walking distance, allowing guests to experience the area's shops, restaurants, cafés, and marina without ever needing to get in the car. Inside, the home is filled with warmth and character. Cathedral ceilings create an open, airy atmosphere, while large windows fill the living spaces with natural light. The thoughtfully designed floor plan offers flexibility for families, professionals working remotely, or multi-generational guests, with comfortable living areas that invite everyone to gather after a day exploring the region. The spacious kitchen flows effortlessly into the main living and dining areas, making everything from morning coffee to family dinners feel relaxed and inviting. Comfortable bedrooms provide peaceful retreats, while the home's flexible lower level and separate entrance offer additional space for guests, a recreation room, or a private work-from-home environment. Step outside and discover your own private oasis. The beautifully landscaped side yard is designed for entertaining and relaxation, complete with a hot tub, outdoor dining space, and plenty of room to unwind beneath the stars. Whether you're enjoying a summer barbecue, relaxing after a round of golf, or soaking away tired legs after skiing Blue Mountain, this outdoor space becomes an extension of the home. Experience Every Season Winter transforms the region into one of Canada's premier ski destinations. Blue Mountain Resort and the area's renowned private ski clubs—including Georgian Peaks, Craigleith, Alpine Ski Club, Osler Bluff, and Devil's Glen—are all just minutes away, making this an exceptional seasonal base for ski enthusiasts. When the snow melts, Collingwood comes alive with boating, cycling, hiking, paddleboarding, golf, and waterfront festivals. Walk to Sunset Point Beach for an evening swim, cycle along the Georgian Trail, or spend the afternoon browsing the boutiques and patios that have made downtown Collingwood one of Ontario's favourite four-season communities. Autumn brings spectacular colours throughout the Niagara Escarpment, while spring offers quiet trails, fresh air, and peaceful waterfront mornings. Live Like a Local Unlike a traditional vacation rental, Sunset Point Retreat offers the comfort and functionality needed to truly settle into life in Collingwood. Whether you're staying for a month, an entire ski season, or an extended summer getaway, you'll enjoy the flexibility and space to experience the region the way locals do. At Seasonal Properties, we believe the best homes offer more than luxury—they create opportunities for unforgettable experiences. Sunset Point Retreat combines an exceptional location, timeless character, and outstanding year-round recreation to deliver one of Collingwood's most inviting seasonal homes. Whether your days are spent skiing fresh powder, boating Georgian Bay, golfing championship courses, or simply enjoying sunset walks along the shoreline, this remarkable property offers the perfect place to call home for the season.
$17,000/season
chalet
5
Beds
4
Baths
10
Guests
$65,000/season
chalet
3
Beds
3
Baths
7
Guests
$18,000/season
apartment
2
Beds
2
Baths
5
$3,500/month
Welcome to your Osler Bluff Luxury Ski Chalet, an exceptional five-bedroom seasonal retreat designed for families and friends who want to experience winter in The Blue Mountains in comfort, style, and complete relaxation. Ideally located on Grey Road 19 and just seven minutes from Osler Bluff Ski Club, this spacious chalet puts your family within easy reach of the slopes while offering something equally important at the end of the ski day: a home you'll genuinely look forward to coming back to. With five bedrooms, a two-car garage, private hot tub, sauna, golf simulator, and generous spaces for entertaining, this isn't simply a place to sleep between ski days. It's a destination in itself. Seven Minutes to Osler Bluff Ski Club - For an Osler Bluff family, location matters. Being approximately seven minutes from the club means mornings can be relaxed, first tracks are always within reach, and getting children back and forth from skiing doesn't become an event in itself. Blue Mountain Village is also approximately 12 minutes away, while Collingwood and Thornbury are both within about 15 minutes, putting dining, shopping and four-season recreation close at hand. Spend the day skiing Osler and return home to your own private après-ski retreat. Five Bedrooms Made for Family & Friends With five bedrooms, the chalet offers the space needed for an extended ski season rather than simply a weekend getaway. Families can unpack, settle in and make the property their own for the winter. There is plenty of room for children, grandparents and visiting friends, making it especially appealing for families who enjoy entertaining throughout the season. Multiple gathering spaces also mean everyone doesn't need to be doing the same thing at the same time. Adults can relax and catch up while the kids have their own space to unwind after a day outside. Your Own Private Après-Ski Club Some of the best moments of ski season happen after the final run of the day—and this property has been designed to make those moments memorable. Come home, take off the ski boots and head straight for the private hot tub. Let tired legs recover in the warmth while the snow falls around you, or retreat to the sauna for the perfect way to warm up after a cold day on the mountain. Later, turn the evening into a friendly competition in your private golf simulator. For golfers who spend the winter counting the days until the courses reopen, it's a fantastic addition. Play a round with friends, work on your swing, or organize family competitions without ever leaving the chalet. With a golf simulator, sauna and hot tub all at home, there's no shortage of entertainment when the lifts close. Built for a Real Ski Season One of the biggest differences between a great vacation property and a great seasonal home is functionality. The two-car garage is a significant advantage during a Southern Georgian Bay winter, providing protected parking as well as valuable space for skis, boots, helmets and all the equipment that comes with an active family. With five bedrooms and plenty of room to spread out, this is a home where you can establish a routine for the season—rather than feeling as though you're living out of suitcases every weekend. Wake up, make breakfast, head to Osler, come home for lunch if you choose, ski the afternoon and finish the day in the hot tub or sauna before dinner. That's what seasonal living is supposed to feel like. More Than a Winter Chalet While this property is exceptionally well suited to ski season, its location makes it equally compelling throughout the rest of the year. The Blue Mountains and Southern Georgian Bay are among Ontario's great four-season recreational destinations, with outstanding golf, cycling, hiking, mountain biking and Georgian Bay all nearby. During the warmer months, trade the ski boots for golf shoes and spend your days exploring the area's courses before returning home for an evening outside. Hiking and cycling routes stretch throughout the Niagara Escarpment, while Georgian Bay provides endless opportunities for swimming, paddling, boating and days by the water. Collingwood, Thornbury and Blue Mountain Village offer restaurants, cafés, shops and entertainment throughout the year. Your Osler Bluff Home for the Season. There is something special about having a true home base in ski country. It's having your equipment waiting in the garage rather than packing it every Friday. It's waking up after an overnight snowfall knowing Osler Bluff is only minutes away. It's friends coming back to the chalet after skiing for drinks, dinner and a round on the golf simulator. It's watching the snow fall from the hot tub before warming up in the sauna. And it's having five bedrooms so the people you want to share those experiences with can be there too. Osler Bluff Luxury Ski Chalet brings all of those elements together in one exceptional seasonal property—offering location, space, recreation and comfort just minutes from the slopes. For families looking to make The Blue Mountains home for the ski season, this is exactly the type of property that turns a great winter into an unforgettable one.
Blue Mountain Retreat on Brooker Blvd. Welcome to Blue Mountain Retreat on Brooker, a comfortable and inviting 3-bedroom seasonal home ideally located on Brooker Boulevard, just minutes from Blue Mountain Village and the ski hills. Perfectly positioned for families looking to enjoy an entire winter in The Blue Mountains, this property offers a fantastic central location with easy access to Craigleith, Alpine, Osler Bluff, Georgian Peaks and Blue Mountain Resort. The home features a bright, open-concept living area with vaulted ceilings, a cozy gas fireplace, comfortable bedrooms and additional recreation space — ideal for relaxing and entertaining after a full day on the slopes. One of the property's greatest advantages is its location. Enjoy the convenience of being close to Blue Mountain Village, with its restaurants, shopping, après-ski and entertainment, while downtown Collingwood, Georgian Bay and nearby trails are all within easy reach. Rather than commuting north every weekend, settle in for the season, keep your skis ready and enjoy everything that makes winter in The Blue Mountains so special. Available for monthly and extended seasonal rentals of 30+ days, including the full winter ski season. Inquire with Seasonal Properties today and make Blue Mountain Retreat on Brooker your family's home for the ski season!
Guests
A Four-Season Retreat in the Heart of Collingwood Welcome to a beautifully positioned Collingwood seasonal rental located within the sought-after Cranberry Resort community. Designed for effortless living, this 3-bedroom, 2-bathroom townhome offers the perfect blend of comfort, convenience, and access to one of Ontario’s premier four-season destinations. Tucked into a quiet, private enclave, the property delivers a sense of calm while being just minutes from everything — from skiing and trails to the waterfront and downtown Collingwood. Designed for Comfortable, Seasonal and Mid-Term Stays This thoughtfully designed home features a bright, open-concept layout ideal for seasonal living: Two well-appointed bedrooms with flexible sleeping arrangements Two full bathrooms for comfort and convenience Open kitchen, dining, and living spaces Natural light throughout with views of mature trees The layout supports both everyday living and entertaining, making it ideal for couples, small families, or professionals seeking a longer-term stay. Effortless Indoor-Outdoor Living - Enjoy a seamless connection to the outdoors: Private patio or balcony space Quiet surroundings within a landscaped community Access to nearby trails and green space Whether enjoying a morning coffee or unwinding after a day of activity, the setting offers both privacy and connection to nature. Location – The Best of Collingwood & Blue Mountains Perfectly positioned for four-season living: Minutes to Blue Mountain Village Close to Georgian Bay beaches and waterfront Access to Cranberry Golf Course and trails Near downtown Collingwood shops and restaurants This location allows you to move effortlessly between mountain, town, and water, capturing the full seasonal lifestyle. Four-Season Lifestyle, Simplified This home is ideal for: Ski season stays near Blue Mountain Summer living with access to trails and waterfront Fall escapes surrounded by colour Remote work in a peaceful, connected setting It offers a low-maintenance, lifestyle-driven approach to seasonal living. Flexible Monthly & Seasonal Availability Available for monthly and extended seasonal stays (30+ days). Inquire today to experience effortless seasonal living in Collingwood — where comfort, location, and lifestyle come together.
Guests
Welcome to a beautifully appointed Mountain House seasonal rental in the Blue Mountains, offering a refined and peaceful retreat designed for extended stays. Set within one of the region’s most sought-after communities, this 2-bedroom, 2-bathroom residence blends contemporary alpine design with effortless access to four-season adventure. Perfectly positioned just minutes from Blue Mountain Village and the surrounding ski clubs, this home offers the ideal balance of proximity and privacy — allowing you to experience the energy of the mountain while retreating to a quiet, design-forward setting. Designed for Comfortable, Modern Living Inside, the home features a bright, open-concept layout where kitchen, dining, and living areas come together seamlessly. Clean lines, natural materials, and thoughtful finishes create a warm, contemporary atmosphere ideal for both relaxing and entertaining during longer stays. The two-bedroom configuration is perfectly suited for couples, small families, or professionals working remotely, while the two full bathrooms provide comfort and functionality for seasonal living. Large windows throughout invite natural light and connect the space to the surrounding landscape. A Community Built Around Lifestyle Mountain House is known for its curated lifestyle and access to premium amenities, offering a unique residential experience in the Blue Mountains: Scandinavian-inspired design and architecture Access to community amenities including heated pools, sauna, and fitness spaces* Walking trails and natural surroundings Quiet, elevated setting just outside the village (*Amenities may vary seasonally) This is a community designed for those who value both wellness and lifestyle. Four-Season Living, Seamlessly Connected From winter ski days to summer lake living, this property places you in the centre of everything that defines the Blue Mountains: Minutes to Blue Mountain Village Close to Craigleith, Alpine, and Georgian Peaks ski clubs Access to hiking, biking, and golf Nearby Georgian Bay beaches and waterfront The Blue Mountains and Collingwood region is widely known as a premier four-season destination, offering year-round outdoor recreation and lifestyle appeal. A Refined Seasonal Escape Whether you are planning a ski season rental, a summer retreat, or a longer-term lifestyle stay, this Mountain House residence offers a seamless blend of comfort, design, and location. This is not a short-term stay — it is an opportunity to live the season fully. Flexible Monthly & Seasonal Availability Available for monthly and extended seasonal stays. Inquire today to secure your place in Mountain House — where modern design meets mountain lifestyle.