Family-friendly vacation rentals in Dufferin County

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Top-rated family-friendly rentals in Dufferin County

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favourite
A winding path is framed by tall trees, leading to a rustic cabin nestled among the forest. Lush greenery flanks the path, creating a serene and secluded ambiance, inviting exploration into the natural surroundings.
Tiny homes in MONO
4.93 out of 5 average rating, 155 reviews

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 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.

Top guest favourite
An outdoor pool area features a surrounding deck with wooden steps leading up to it. Bright blue water reflects the sky, and vibrant green grass borders the patio. Two red Adirondack chairs are placed nearby, complemented by lush trees and a distant green landscape.
Guesthouse in Orangeville
4.95 out of 5 average rating, 374 reviews

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
This inviting bedroom features a spacious bed adorned with soft linens and a textured throw. A large armoire stands alongside, complemented by decorative plants and soft lighting. Natural light is welcomed through an adjacent glass door leading to a private entrance.
Guest suite in Orangeville
4.92 out of 5 average rating, 795 reviews

Hot Tub Fall Colours Getaway - Headwaters Retreat

Escape to our rustic-modern Queen Suite, perfect for your getaway. Relax in the private hot tub right outside your door, unwind by the fireplace & enjoy Netflix & Amazon TV. This cozy retreat features a private entrance, ensuite bathroom, and a second bedroom with twin beds. Steps from scenic hiking trails, minutes from the town center, your stay is ideal for outdoor adventures, wine tours, weddings, work trips or just quiet escape away. Book now for your ultimate getaway in comfort and nature!

Guest favourite
A spacious sleeping area is furnished with a queen size bed adorned with a patterned duvet and two pillows. A nightstand stands beside the bed, and a lamp provides light. Two nature-themed artworks hang on the wall, complementing the neutral tones of the room.
Guest suite in Shelburne
4.87 out of 5 average rating, 141 reviews

Entire spacious basement with 1bedroom & Kitchenet

Relax with the family or friends at this peaceful and immaculate place. Accommodates up to 4 people with the comfortable sofa bed in den. NON-SMOKING NO PETS. FULL KITCHEN NOT AVAILABLE. KITCHENET AVAILABLE. Full, clean washroom. Spacious room, a queen size bed, dining table sits six, kettle, grill, basic utensils and kitchen wear, linen, towels, and drinking water. 50 minutes away from Collingwood, Wasaga Beach, Berrie, Blue Mountain & Brampton. Lots of food options available in Shelburne!

Superhost
A wooden bunkie is nestled among the trees, featuring a porch that leads to a BBQ grill and a hot tub. Surrounding greenery creates a serene environment, while sunlight filters through the forest canopy, highlighting the natural beauty of the area.
Tiny homes in Horning's Mills
4.89 out of 5 average rating, 152 reviews

Pine River Bunkies: Heron’s Landing Off Grid Cabin

Follow the forest pathway to our 2 new 'glamping' bunkies. Heron's Landing is set into the hillside beside a spring and is surrounded by natural beauty. Just 1 hr from Pearson and 45 min. to Georgian Bay, Mulmur straddles the Niagara Escarpment, a UNESCO World Biosphere. Our 11 acres borders 400 acres of conservation land in the Pine River Valley including part of the Bruce Trail. We can accomodate families, friends or groups onsite. Not a camper? Please consider our 'in house' listings.

Top guest favourite
A private wooden deck is shown with an umbrella-covered table and four chairs, surrounded by lush greenery. Windows on the building's façade allow natural light, while potted plants add a touch of color, enhancing the outdoor space for relaxation.
Apartment in Horning's Mills
4.96 out of 5 average rating, 310 reviews

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.

Top guest favourite
A spacious living area features a blue sofa with a light throw, positioned beside a circular coffee table. Wall art adorns the white walls, and natural light filters through a decorative window. A white cabinet and a small plant complete the cozy atmosphere.
Loft in Mono
4.98 out of 5 average rating, 141 reviews

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.

Top guest favourite
A spacious living area is equipped with a large sectional sofa and a rounded ottoman. A flat-screen television is mounted on the wall, while a mirror reflects natural light from the sliding glass doors leading to an outdoor patio. Plants are arranged to enhance the decor.
Cabin in Orangeville
4.97 out of 5 average rating, 175 reviews

Hockley Valley Cozy Cottage

Take it easy at this unique and tranquil setting where the entire property is yours! Freshly renovated cottage only 600M from Hockley Valley Resort and also close to restaurants and hiking trails. This cottage sleeps 4 comfortably with separate bedroom. Picturesque setting directly on Nottawasaga river with mature gardens and plenty of outdoor space. Morning coffee or afternoon drinks under the covered gazebo at the waters edge or relax in the hammocks, this place truly has it all.

Top guest favourite
A modern living area is presented with two light grey sofas facing a glass coffee table, which rests on a decorative rug featuring shades of blue and neutral tones. Natural light enters through two windows, highlighting the stylish wall decor.
Apartment in Shelburne
4.92 out of 5 average rating, 103 reviews

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.

Guest favourite
A seating area is featured with a modern grey sofa and a bright yellow armchair, positioned on a light rug. A ping pong table is visible in the background, alongside a green wall adorned with foliage and illuminated with a neon sign.
Home in Orangeville
4.91 out of 5 average rating, 118 reviews

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!

Top guest favourite
A modern living area features a sleek gray sofa flanked by decorative pillows. A glass coffee table sits atop a circular patterned rug, with decorative items placed on it. Natural light enters through two windows dressed with sheer curtains, while a door leads to another room.
Apartment in Shelburne
4.98 out of 5 average rating, 252 reviews

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.

Top guest favourite
A cozy living area features a light-colored sofa with decorative cushions, a coffee table, and a wall-mounted television. A slim electric fireplace is situated beneath the TV. To the rear, a fully equipped kitchen can be seen, enhancing the space's functionality.
Guest suite in Orangeville
5 out of 5 average rating, 163 reviews

Garden Studio Apartment

Enjoy a stylish experience at this centrally located place. 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.

Popular amenities for Dufferin County family-friendly rentals