House holiday rentals in Dufferin County

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.

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.

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.

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.

Stylish 3BR | Hot Tub • Firepit • Cozy Fall Escape

Welcome to your relaxing escape in the heart of Alton—a cheerful and spacious 3-bedroom, 1.5-bathroom home backing onto the beautiful Credit River. Perfect for families, friend groups, wedding guests, or anyone craving peace, nature, and comfort. • 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

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.

Mono Mills Home next to the County Great Getaway

We are located in quiet hamlet of Mono Mills, which is 8 miles to Palgrave and 16 miles to Erin. Orangeville / Caledon area, Ontario, Mono Village. Just Off Airport Rd and Hwy9 area. Cute and Cozy. Sleeps 2-3 people. $1575++ per week, Monthly discounts. Non Smoking. Clean, comes with all linens, utensils, pots/pans, BBQ, Large TV, Cable and Internet. Weekly or Monthly Only. This property is a brand new self-contained In-law suite. airbnb.ca/h/monomills

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.

Upper level 2 bdrm apt

Take a break and unwind at this peaceful oasis. In brand new house, brand new 2 bedroom apartment suited for two or max 4 adults, located in conservation area with lakes, beaches, nature trails, horseback riding, hike, canoe or cycle in natures playground. In winter time can downhill ski, cross country ski, skating, ice-fishing, snowmobile and much more. Please check the websites for details.