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
5
Beds
4
Baths
10
Guests
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.
$75,000/season
chalet
3
Beds
3
Baths
7
Guests
$28,000/season
house
5
Beds
4
Baths
10
Guests
$5,500/month
chalet
6
Beds
3
Baths
10
Guests
$22,000/season
Welcome to Brooker Blvd. Mountain Retreat, a beautifully positioned Blue Mountains seasonal rental offering the perfect balance of privacy, comfort, and convenience. Located in one of the most desirable pockets near Blue Mountain Village, this thoughtfully designed 3-bedroom, 3-bathroom detached home is ideal for families and professionals seeking an elevated seasonal lifestyle in the heart of Ontario’s premier four-season destination. Just a 15-minute walk to Blue Mountain Village and only minutes from the ski hills, this home allows you to fully immerse yourself in mountain living while enjoying the privacy of a quiet residential setting. Designed for Comfortable Seasonal Living This beautifully maintained home features a unique reverse floor plan, with the main living area located on the upper level to maximize light, views, and openness. The spacious open-concept second floor showcases: Vaulted ceilings Bright living and dining spaces Functional kitchen for entertaining Walkout to second-level deck for outdoor dining The layout creates an inviting atmosphere ideal for family gatherings, entertaining guests, or simply relaxing after a day outdoors. Space for Families & Guests The home offers three well-appointed bedrooms, including a comfortable primary suite with: Walk-in closet Private ensuite bathroom The lower level provides additional flexibility with a spacious recreation room complete with: Cozy gas fireplace Bar area Laundry room Additional storage Single garage with room for gear This setup makes the property especially well suited for ski families, extended stays, and those seeking a true home-away-from-home experience. A Private Setting Close to Everything Situated on a private corner lot surrounded by mature trees and gardens, the home offers a quiet and peaceful environment while remaining close to everything the Blue Mountains region has to offer. Nearby amenities include: Public tennis courts Family park Dog park Hiking and biking trails Georgian Bay beaches The result is a rare combination of village access and residential privacy. The Ultimate Blue Mountains Lifestyle Perfectly positioned for four-season recreation, Brooker Mountain Retreat provides easy access to: Skiing and snowboarding at Blue Mountain Private ski clubs including Craigleith and Alpine Golf courses and hiking trails Collingwood and Thornbury dining and shopping Georgian Bay waterfront activities This is an ideal Ski Season hone base!
Welcome to 113 Landry Lane, a beautifully finished custom home located in the highly sought-after community of Lora Bay in Thornbury. Perfectly positioned between Georgian Bay and the Blue Mountains, this exceptional residence offers refined seasonal living surrounded by golf, ski clubs, trails, waterfront access, and one of Ontario’s most vibrant four-season lifestyle communities. Available for extended seasonal stays, the home is ideally suited for guests seeking a six-month summer and fall retreat or a six-month winter into spring stay — offering the opportunity to truly experience life in Lora Bay as a local. From the welcoming front porch to the elegant interior finishes, every detail of this home has been designed with comfort, functionality, and style in mind. The bright open-concept main floor seamlessly connects the living room, dining area, and gourmet kitchen, creating an inviting atmosphere for entertaining and everyday living. The kitchen is a true centerpiece, featuring: Oversized island with seating Bar fridge Double wall ovens Built-in microwave Extensive cabinetry and storage A flexible front office or secondary bedroom provides additional functionality for guests working remotely or accommodating visiting family and friends. The main floor also includes a beautifully appointed laundry room and walkout access to a low-maintenance composite deck complete with gas BBQ hookup — perfect for outdoor dining throughout the warmer months. A Private Primary Retreat & Spacious Guest Accommodations The light-filled primary suite serves as a peaceful retreat, complete with: Walk-in closet Spa-inspired 5-piece ensuite Elegant finishes and generous space Upstairs, a cozy loft creates an additional living area, while two spacious bedrooms share a beautifully designed 5-piece bathroom. The fully finished lower level expands the home’s versatility even further with: Large above-grade windows bringing in natural light Spacious recreation room Two additional bedrooms Another full 5-piece bathroom This layout makes the home ideal for larger families, extended guests, or multi-generational seasonal living. Thoughtful upgrades throughout the home include: Heated-feeling epoxy garage flooring Tesla charger in the 2-car garage Vroom built-in vacuum system for vehicle cleaning Slat wall garage organization system Composite decking and low-maintenance exterior living Every detail has been considered to support effortless long-term stays. Living in Lora Bay means embracing one of Ontario’s premier four-season communities. Residents enjoy access to: Private Georgian Bay beach access Lora Bay Golf Club Fitness and gym facilities Scenic walking and biking trails Vibrant social and recreational community Just minutes away, Thornbury offers charming restaurants, cafés, boutiques, and marina access, while nearby ski clubs and Blue Mountain Resort provide exceptional winter recreation. Perfectly Positioned for Four-Season Recreation This location offers immediate access to: Georgian Peaks Ski Club Craigleith Ski Club Alpine Ski Club Blue Mountain Resort Georgian Bay waterfront Golf, cycling, hiking, and trails Whether enjoying summer evenings by the bay, fall colours throughout the Escarpment, or winter ski days close to the slopes, 113 Landry Lane delivers a complete seasonal lifestyle experience. A Home Designed for Extended Seasonal Stays Ideal for: Six-month summer and fall stays Winter ski season rentals into spring Families relocating or exploring the area before purchasing Golf and ski lifestyle enthusiasts This is more than a rental — it is an opportunity to immerse yourself in the lifestyle and community that define Lora Bay. Flexible Extended Seasonal Availability Available for monthly and extended seasonal rentals, with preference for: Summer & Fall (6 months) Winter into Spring (6 months) Bi-Weekly cleaning management is included in your stay Inquire today to experience life at 113 Landry Lane — where Georgian Bay living, golf, skiing, and community come together in one exceptional Lora Bay home.
Welcome to Duntroon Hideaway, a spacious and beautifully positioned ski season chalet rental nestled in the scenic hills of Duntroon. Surrounded by snow-covered forests, rolling countryside, and Escarpment views, this inviting 6-bedroom winter retreat offers the perfect setting for families and groups looking to fully embrace the ski season lifestyle. Located just minutes from Devil's Glen Ski Club and Highlands Nordic, this property delivers effortless access to some of Ontario’s best alpine and Nordic winter experiences while offering the peace and privacy of a true country escape.Designed for Ski Season Living Thoughtfully designed for extended winter stays, this chalet comfortably accommodates larger families and groups with generous gathering spaces and flexible sleeping arrangements. The home features: Six spacious bedrooms ideal for ski families and guests Hot Tub to unwind after a day on the ski hills Large living and entertaining areas for après-ski evenings Fully equipped kitchen perfect for family meals and hosting Cozy spaces for relaxing after a day outdoors Scenic views of the surrounding countryside and Escarpment Whether warming up after a day on the slopes or enjoying quiet snowy mornings by the fire, Duntroon Hideaway is designed to make winter living feel effortless and memorable. Minutes to Ontario’s Premier Winter Recreation This location is ideal for those wanting immediate access to winter activities while staying removed from the busier resort atmosphere. Nearby winter highlights include: Devil’s Glen skiing and snowboarding Highlands Nordic cross-country skiing and snowshoeing Blue Mountain Resort and private ski clubs Winter hiking and Escarpment trails Charming nearby villages including Creemore and Singhampton for cafés, restaurants, and après-ski outings This is a location where winter becomes a lifestyle — not just a weekend trip. Unlike high-traffic village rentals, Duntroon Hideaway offers: Space and privacy Quiet countryside surroundings Easy access to multiple ski destinations A true chalet atmosphere for the winter ski season It is the ideal setting for families seeking a more relaxed and authentic ski season experience.The Ultimate Winter Basecamp Whether you are planning: A full ski season retreat A family winter getaway A multi-generational holiday stay A seasonal escape close to the slopes Duntroon Hideaway offers the comfort, access, and atmosphere that define exceptional winter living in the Blue Mountains region. Winter Seasonal Availability Inquire today to experience Duntroon Hideaway — where winter, nature, and chalet living come together in one unforgettable seasonal retreat.
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.