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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.

Whispering Pines Cabin in Woodland Acres

Experience this nature retreat just 60 km from Toronto and feel like you’re thousands of miles away. The perfect glamping experience for any nature lover looking to relax. There is power in the bunkie which offers the convenience of lighting, cell phone charging, an electric fireplace, a kuerig coffee maker a mini fridge with freezer and air conditioning. Pursue your favourite outdoor activities during the day and then return to your cozy queen bed and sofa bed just steps away from the bonfire.

A bright & modern urban studio

Come & unwind...in comfort. "The Snug" is a 740 square foot studio-style unit, that is bright & modern. You will be on the basement level of the main house, with a completely separate entrance. Nice kitchen & Sleek 3 pc bathroom(with rainfall shower head and heated floors). The queen bed, with luxury-firm mattress, has built in storage for all your needs. Reliable wifi so you can work at home! A short hop from Toronto, Dufferin County has all you need for a relaxing getaway! Come & See :)

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.

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!

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.

L&S Comfy Suite

Beautiful inviting space for families as well as individuals. Brand New Fully renovated area with lots of amenities for the whole family. 2 Great size bedroom with queen size beds. Jack And Jill full washroom with an amazing shower that boast body jets. Comes with all the bells and whistles. Open concept with Living room, Dining room, Full Kitchen, Washer and Dryer, free parking, work area ideal for remote work, and lots more…. NO UNREGISTERED GUESTS ARE ALLOWED AS PER HOUSE RULES.

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.

Garden Studio Orangeville

🌿 Country-Soul, Town-Heart Haven: Walk to Cafes, Mins to Premium Spas & PGA Golf. A newly renovated 1 bdrm walkout apartment located in our home in downtown Orangeville. Steps to Theatre Orangeville, Orangeville farmers market, and Jazz & Blues Festival. Enjoy evenings on your own patio in a private backyard overlooking the garden. Enjoy walks on the Island lake Conservation Park.. Dine at any of the many fine restaurants or cook at meal in your own fully equipped kitchen.

Rural Estate Coach House Apartment

Peaceful secluded guest house in forest property 5 minutes from Orangeville. We have three active dogs who often demand attention! Can be arranged as a two bedroom with privacy or a one bedroom with extra room. King bed in the large bedroom. Double futon in the sitting room. Fabulous bathroom with views. The guest house is 70 feet from main house. Quiet, nice forest walks. NOT a 'corporate Airbnb' - managed by owner. Near Bruce Trail and Hockley.

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!

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.