House vacation 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!

Tranquil Retreat amongst Nature

Discover the Charm of Honeywood House. Find peace & privacy among the tall maple trees at our chalet style cottage. Perched high up on the hillside and enveloped in a wrap-around covered deck, this is the perfect place to walk the forest trails, breathe deeply and take in the healing energy of nature. The cozy interior is carefully curated with soft lighting, beautiful natural textures and details. See forest views from every window. Enjoy the warmth of a crackling fire in the wood stove.

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.

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.

Fab 2 Bedroom home 3 minutes to Caledon Ski Club!

Welcome to the beautiful village of Belfountain . This charming 2 bedroom fully detached home is located in the village which is nestled in the Caledon Hills. It’s fun, its funky and its classy. Both bedrooms have their own privacy from one another and offer premium bedding and accents. The extra large eat in kitchen offers all the amenities needed. Sliding glass doors from both the kitchen and master bedroom lead you to your private backyard and large deck . Fabulous location to golf/ski.

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

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.

Primrose Park

Little cabin set up in Primrose Park, access to a heated pool shared with the campers in the summer, hiking trails, ride your bicycle, firepit, children's park, volleyball court, basketball court and you can even participate in the activities planned for the campers. Amentities close by includes golfing, fishing, dining and shopping. In the winter there are groomed snowshoe or cross country skiing trails on the property. Snowmobile trail is across the road. Parking included.

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.

Mono Forest Stay

⭐Welcome to our 4BR, 2.5 bath Detached house near Island Lake & Hockley Valley in Orangeville, featuring: ✔ Fully equipped huge kitchen for preparing meals ✔ Cozy family room with a Smart TV ✔ High-speed internet ✔ Comfortable bedrooms with fresh linens ✔ Ping-pong, board games, treadmill, BBQ, deck, and forest views ✔ Ideal for families, groups, or wedding guests. ✔ Private backyard and peaceful vibe. Book your stay with confidence and make unforgettable memories!

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.