House holiday rentals in Dufferin County

Golf,Ski 2 BR Century Home in Downtown Orangeville

Walk to downtown and island lake conservation. Close 10 min drive to Hockley Valley This beautiful 1,250 sqft, 2 bedroom unit sleeps 4 adults comfortably. The 1st bedroom has a queen-sized bed and a walk-out to the 2nd floor furnished deck area (see pictures). The 2nd bedroom has a full sized (double) Has Air Conditioning and features a private deck off the master bedroom The bathroom that has a new shower and stand-alone "claw" bathtub. There is also a newer stackable washer and dryer.

Hockley Valley - Jazzy Pines - 4 BR with Pool

Welcome to your private retreat in the heart of Hockley Valley! Nestled on 9 acres of rolling countryside, this unique two-story home offers breathtaking views, direct access to nature trails, and a perfect blend of rustic charm and modern comfort. The great room boasts floor-to-ceiling cathedral windows, flooding the space with natural light and offering panoramic views of the surrounding landscape. Step outside to your own oasis: a newly renovated pool, expansive deck, and landscaped grounds.

Charming and Peaceful Retreat with Hot Tub

Welcome to your perfect getaway in this spacious and inviting large house, designed for comfort and relaxation. Nestled in a peaceful neighborhood, this property boasts a private backyard with a beautiful view and Hot Tub. The expansive yard offers plenty of space for outdoor activities, making it ideal for families and groups. Enjoy morning coffee on the patio, host a barbecue, or simply bask in the serene surroundings. 14 min to the famous and popular TPC Toronto Opsrey Valley Golf Course

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.

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 | Pool, Hot Tub, Firepit & River Relax

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

Stylish 3 Bedroom Getaway in Orangeville

Nestled among tree sculptures and lakes, just steps away from downtown and minutes from the serene beauty of Island Lake Conservation Area. Our urban oasis is complete with a comfortable bed, fully equipped kitchen, chic living area, and private balconies. Be transported through time as you wander the streets of downtown, admiring vintage architecture and vibrant culture. Experience the magic of nature and city living combined in one unforgettable stay!

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

Luxury Hockley Estate Spa

Kick back and relax in this calm, stylish space. This home is located in a central location close to Orangeville and hockley Valley ski/ winery/hiking. The home is just like a relaxing spa with pool, hot tub, sauna, indoor wood burning stove, outdoor BBQ, massive kitchen, lots of space. Great for family dinners and getaways, we enjoy groups with longer stays and will give monthly discounts.. This amazing property has it all:)