Vacation rentals in Dufferin County

Sunny Pines Farm Studio Tennis Court/Bruce Trail

Perfect for a getaway in the country. A bright, spacious, open-concept designer studio featuring beautiful rolling-hill vistas, queen bed, 3-piece bathroom, dedicated bbq, heat/AC plus a wood burning stove, wet bar with a Nespresso machine, deluxe counter-top oven & bar fridge and all new tennis court, laundry available upon request. Mono Cliffs, Boyne Valley, Hockley Valley Nature Reserve Prov. Parks & Mansfield Recreation Centre are minutes away. Ideal hiking, cycling, snowshoeing and xcsking.

Beautiful Riverside Country Apartment

Bright, warm and newly renovated, this 900sqft apartment, a private floor of a charming country home with separate entrance and garden patio, awaits you in Melancthon. SmartHDTV, Wifi, tranquil surroundings, and the Bruce Trail. Close to Shelburne, Mansfield, Creemore, Pine River Institue and many excellent restaurants (The Globe and Mrs Mitchels). Only 40 minutes to the Scandinave Spa, Collingwood, Blue Mountain, Wasaga Beach. Golf Courses are close by. A perfect retreat just north of Toronto.

The Bee Hive - Lower Level Raised Bungalow

Kick back and relax in this calm, stylish and super equipped space. Fully self contained and private lower apartment to our home with a separate apartment above. Open plan kitchen dining living area with 1 bedroom (queen bed) and 1 shower room with 8 ft ceilings. Recently renovated almost everything new ready for the 2025 season. Home from home, calm and pleasant space with all the mod cons. 50" LG Smart TV, Full sized fridge freezer, dishwasher, stove, microwave and much more - Enjoy!

Tamarack Trails Wilderness Cabin

Welcome to Tamarack Trails, your peaceful escape nestled in a quiet forest. This luxury cabin offers the perfect blend of comfort and nature, surrounded by 40 acres of unspoiled wilderness. Drift off to sleep in a cozy queen-sized bed and wake to the sound of song sparrows. Soak in a relaxing tub as you gaze out floor-to-ceiling windows. Enjoy breakfast on your private deck. Spend your days wandering private trails with stunning scenery or snowshoe through snow-draped white pines in winter.

The Trails Retreat (Private Cabin)

Beautifully renovated 2-story private hilltop cabin for romantic getaway, family stay or friends' retreat, experience a taste of the country together. Backed by forest and trails and set away from our family home, minutes to the Bruce Trail, Hockley Ski & Golf Resort, Mansfield Ski Club and charming Orangeville. Enjoy total guest privacy & spectacular sunrises. Guests are welcome to share our heated pool in season:) Add a playful Yoga/Functional Movement class or chef's dinner to your stay!

Hockley Riverside Cottage • Loft and Bunkie

Needing an unforgettable escape? This cozy cottage is nestled in nature along the Nottawasaga river and has large panel doors that fully open for picture worthy views & peaceful sounds of the river. A new incredible outdoor fire-pit with hanging egg chairs. A cozy indoor wood burning fireplace along with a comfy pull out couch that has a projector above for the best movie nights. Heated floors if you aren't interested in maintaining a fire, fully equipped kitchen, Wi-fi, AC and washer/dryer.

1850 Settler's Cabin in Private Forest

Our beautiful 1850 settler's log cabin is simply furnished and does not have plumbing. Electricity is powered by a honda generator. Fresh drinking water is supplied. Bathroom is a clean, private outhouse and guests have access to our centralized guest shower facility on premises from 6-9 am/pm daily. As your Bed and Breakfast host we will personally greet you and check you in and always remain on property while offering you privacy. We are designed for a quiet, peaceful rustic getaway.

Cabin in Mono.

Escape to Maple Lane Log Cabin, a secluded 1880s retreat set on 7.6 private acres surrounded by mature maples and breathtaking perennial gardens. Inside, rustic charm meets cozy comfort with a wood-burning fireplace and warm, inviting spaces. Sip coffee on the deck, wander the grounds, and unwind to peaceful countryside sounds. Perfect for couples or solo getaways seeking quiet, nature, and a touch of history. At Maple Lane Log Cabin, serenity isn’t just a feeling — it’s an experience.

8 Acre Retreat | 5 min to TPC Osprey + Hot Tub!

Enjoy peaceful summer evenings on the patio ☀️ surrounded by nature on a private 8-acre property only 1 hr from Toronto. • 8 min from TPC Osprey 🏌️ • 2 spacious primary bedrooms w ensuites • Electric fireplace • Starlink Wi-Fi 🌟 • Smart TV • Private & nearby nature trails Start your mornings w coffee on the patio. Spend the day exploring trails or golfing nearby, then unwind at your calm, stylish retreat. Perfect for families, couples, & golfers looking to escape the city.

Hockley Haven

Kick back and relax in this calm, stylish space. Cozy 1 bedroom carriage house loft (appx 650 sq ft) above detached 3 bay garage in serene country setting on 5 acres of pine and cedar with a river running thru it. Pullout couch can accommodate 2 additional people. Walk across the road to Pollinator Garden & Island Lake Trails. 6 min drive to Hockley Valley Resort and Adamo Estate Winery, as well as beautiful downtown Orangeville boasting fabulous restaurants and quaint shops.

Uniquely Pure Cozy Bunkie - 10 min to Elora Gorge

Stay in a cozy Bunkie, with outdoor shower (seasonal), and Uniquely Pure Studio on sight. Pack for winter❄️; propaine heated, blankets, and water provided. Dishes taken care of in winter. Let me know if you want separate sleeping arrangements if your'e a group of 2 in advance. PACK YOUR OWN WOOD PLEASE DO NOT USE ANY OF THE WOOD ON PROPERTY. There is a pull out double bed couch with bedding provided all underneath the couch in bags and sheets underneath the coffee table lid.

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!