Holiday houses in Orangeville

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Top-rated holiday rentals in Orangeville

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Guest favourite

Guesthouse in Orangeville

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.

Guest favourite

Dome in Bradford West Gwillimbury

Four season glamping dome under the stars

Whether you are looking for a romantic getaway for two, a solo remote work week in solitude surrounded by nature, or a family adventure, this 4-season geodesic dome is just the right place. Explore picturesque trails of Scanlon Creek Conservation Area, enjoy inground pool in summer, experience breathtaking sunsets over the farm fields, the starry skies by the bonfire, mesmerizing dance of fireflies in June, and let the frogs and crickets lull you to sleep in the place where time stands still...

Guest favourite

Tiny home in Mulmur

Paradise Pines Bunkie (1 of 3) 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 for a relaxing getaway. There is power in the bunkie which offers the convenience of lighting, cell phone charging, an electric fireplace, a kuerig coffee maker and mini fridge with freezer. Pursue your favourite outdoor activities during the day and then return to your cozy queen size bed and sofa bed just steps away from the bonfire.

Guest favourite

Rental unit in Horning's Mills

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 next to the Bruce Trail. Close to Shelburne, Mansfield, Creemore, and many excellent restaurants (like The Globe and Mrs Mitchels). Only 40 minutes to the Scandinave Spa, Collingwood, Blue Mountain, and Wasaga Beach. Golf Courses are close by. A perfect retreat just north of Toronto.

Guest favourite

Loft in Mono

Hockley Haven

Kick back and relax in this calm, stylish space. Newly renovated 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.

Guest favourite

Place to stay in Mono

Rural Estate Coach House Apartment

Peaceful secluded guest house in forest property 5 minutes from Orangeville, 1 hour from downtown Toronto. 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.

Guest favourite

Guesthouse in Orangeville

A bright & stylish urban studio

Come & relax...in privacy. The "Carriage House" is a 634 square foot studio-style unit is unique & intimate. You will be away from the main house, in your own building. Amazing kitchen, complete with gas range. Spacious & elegant over-sized bathroom. The Murphy bed has a luxury-firm queen mattress, & stows away in a snap for your convenience. Diner booth for meals, or working at home! A short hop from Toronto, Dufferin County has all you need for a relaxing getaway! Come & See :)

Guest favourite

Guest suite in Orangeville

Private Hot Tub - Headwaters Retreat

Escape to our cozy and rustic queen suite with a modern touch. Private entrance & hot tub steps from your door, overlooking our peaceful conservation area. Spacious fireplace in main suite with en-suite bathroom, Apple TV, Netflix, and second bedroom with two twin beds. Steps from the hiking trails and just minutes from the town center. Perfect for outdoor adventures, art gallery visits, wine tours, weddings, sporting events, work trips or just a quiet getaway. Your getaway awaits!

Guest favourite

Cabin in Mono

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:) Chef's creations and Private yoga and group classes available

Guest favourite

Guest suite in Mono

Mono - Charming, Rustic 150 Year Carriage House

This rustic space is perfect for a weekend getaway, year round. Close to ski hills, nature trails and the quaint town of Orangeville the Carriage house will provide you the authentic feel of our iconic cabin in the woods with the sophistication and comforts of your personal retreat for the weekend. The interior design is eclectic, funky and perfectly contrasts the rustic charm of the 140 year old, hand cut wooden beams and the overall log cabin environment.

Guest favourite

Rental unit in Shelburne

A&M Cozy Home Away From Home

Bring the whole family to this great place with lots of room for fun. Guests can enjoy this beautiful modern 2 bdrms with queen size beds, legal/separate entrance apartment equipped with kitchen appliances, microwave, stove, dishwasher, fridge, toaster, coffee maker, pots, plates, utensils, separate laundry. Equipped with your comfort in mind. It offers shampoo, conditioner, body wash, towels, keyless entry. Ignite TV premier PKG, Netflix, free 500 mbps Wifi.

Guest favourite

Guest suite in Orangeville

The Spoke - Private basement apart. near downtown

Cozy basement apartment in family home: nope, not a vintage farmhouse nestled in the countryside but conveniently located in town and close to recreation, shopping, dining, business and special event/banquet locations. Living room, galley kitchen, bedroom with adjacent bathroom. Did we mention it's a basement? Yes, there are some stairs, and an HVAC bulkhead in living room and bedroom w/ 6'2" clearance. Check us out on Instagram at @thespokeov