House holiday rentals in Dufferin County

Dufferin Retreat

Nestled in the heart of Shelburne, this stylish home offers a serene escape located just a short stroll from Shelburne's best restaurants, shops, and parks. This gem backs onto the rail-trail for convenient summer morning walks or bike rides, and miles of snowmobiling in the winter. Fully furnished and beautifully designed, it boasts a calm, cozy atmosphere you're sure to love. Experience the perfect blend of tranquility and accessibility in this Shelburne Retreat. We look forward to your stay!

Country Retreat in Hockley Valley

Our country house is a perfect place to unplug and unwind surrounded by natural beauty. Sit and watch the birds from the back porch or walk in the woods by a running stream or cosy up in front of the fireplace with a good book. We are down the road from Mono Cliffs Provincial Park, part of the Bruce Trail, with great walking trails for experiencing amazing fall colours. We have a fully functional kitchen and a big country dining table to easily enjoy great group dinners. It's a doggie heaven.

Peaceful retreat on 10 acres

Forget your worries in this spacious and serene space. Very private with scenic views from all the windows. Vaulted ceiling in post and beam style home. Cosy gas fireplace in living room. Main floor bedroom with ensuite bathroom - walk in shower and free standing tub. Open loft overlooking the living room with two bedrooms, family room and bathroom. Huge deck space with 2 person hot tub and views of the wildflower gardens and surrounding woods. *Special rates for longer stays available

Orangeville 3BDRM House

This home can accommodate an escape from the city to relax/explore or offer a quiet place to work or recharge if on a business trip. This clean & cozy townhouse is perfect for the whole family. Enjoy a full kitchen stocked with coffee, sugar, honey & spices. The dining area sits 4 with some bonus additional seating at the nearby island. The living room has a large couch with 2 additional seating options that have a clear view of the television. There are 3 fantastic spacious bedrooms.

Cozy Cabin Vibes - Hot Tub• Firepit• Snowy Retreat

Escape to our riverside cabin this winter—soak in the hot tub under falling snow, curl up by the fire, and enjoy cozy evenings surrounded by nature. Perfect for couples, families, a ski weekend away, girls’ weekends, or a quiet work-from-home retreat. • Sleeps up to 8 guests comfortably • 3 cozy bedrooms (2 with private decks!) • 1.5 bathrooms • Fully equipped kitchen + BBQ patio for year-round grilling • Stylish living room with fireplace & smart TV • Fast Wi-Fi, workspace-friendly

Unwind & Explore at Hockley Valley Coach House

The Coach House is a charming country retreat an hour from Toronto. Perfect for a staycation, ski weekend, or working from home, it features a chef’s kitchen for cozy meals, gathering with friends, and entertaining. In winter, enjoy skiing, snowshoeing, and peaceful snowy hikes. Hike the Bruce Trail, explore local markets, or unwind in nature. Ideal for short- or long-term stays during home renos or extended visits, offering a warm, relaxing retreat with comfort and charm in every season.

JJ’s small town country retreat

Take a step back in time to this old farm house. Located on the corner of our little town called Badjeros. This house was built in the 1930s and it’s been in our family for over 80 years. Since then there has been numerous upgrades to the house as well as a large 1200 square foot open concept addition built onto the existing house. While out in the country, this house is central to many attractions in the area 1.5 hours south of Toronto/GTA. Blue Mountain/ Collingwood is 30 minutes north.

A Modern 3 Bedroom Home with Free Parking & Wifi

Welcome to our modern 1000sf single-story bungalow in the charming town of Orangeville. Thoughtfully designed for comfort and convenience, this bright and stylish space offers a peaceful retreat just minutes from the vibrant shops, restaurants, and cafes along historic Broadway. Whether you're here to explore the scenic trails at Island Lake Conservation Area, enjoy the local arts scene, or simply relax in a cozy, well-appointed home, this bungalow is the perfect base for your stay.

Modern Cozy Getaway near Headwaters Hospital

Welcome to your perfect modern, stylish, and cozy get away. This home offers the spacious interiors, thoughtfully curated décor, and all the comforts of home. Located in the heart of town, you’ll have easy access to local ski attractions, winery, dining, and entertainment, making it an ideal spot for both leisure and business travelers. Whether you’re unwinding in the beautifully designed living spaces or exploring the vibrant surroundings, this home is your perfect retreat.

House on the bank of river

This rural country home was built in 1960's. 7 acres of land with river passing through it, this private house is located just outside the town of Grand Valley. Two bedrooms with each having its own queen bed, this is perfect for a party of up to 4. Big kitchen with gas stove, fridge, microwave, you can do your own cooking. ✅ Wi-Fi ✅ TV Box with Netflix ✅ Full Kitchen The space Guest have access to main floor, entrance to basement and sunroom is prohibited to guests.

Central OVille,3 bed Victorian, walk to Lake, pets

This 3 bedroom (4 beds), 1,500 sqft unit with new Gas Fireplace and central A/C sleeps 6 adults comfortably. Bedroom 1 has a queen-sized bed, another a double bed while Bedroom 3 contains two separate single beds. There is large and beautiful private deck and fenced back yard that contains a full-sized BBQ The unit contains: Washer and dryer (within the unit), hard-wood floors, and free high-speed unlimited internet and HD Cable.

Brand New Entire Home in Southgate ( Dundalk)

Bring the whole family to this great home with lots of room for to create good memories. Dundalk is a great cute town to go for hiking , skiing , snowboarding, snowmobiling. Nice great trails are in town. 20 minutes to Shelburne, 40 minutes to Collingwood 45 minutes to Blue Mountain. Roughly about hour to Brampton. This is where Wind Mills and farming landscapes and newer Sub division.