Family-friendly vacation rentals in Orangeville

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Orangeville

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

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Guest favorite

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 home in MONO

4.92 out of 5 average rating, 146 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 favorite

A studio room features a spacious bed with crisp linens and a decorative throw. Comfortable seating areas include armchairs and a small table. Natural light filters in through the windows, enhanced by a ceiling fan overhead. The kitchen and dining area are visible in the background.

Guesthouse in Orangeville

4.96 out of 5 average rating, 137 reviews

A bright & stylish urban studio

Come & relax...in privacy. In the "Carriage House" you will be away from the main house, in your own building! Its a 634 square foot studio-style unit, that is unique & intimate. A nice sized kitchen, complete with gas range. Spacious & bright over-sized bathroom. The Murphy bed has a luxury-firm queen mattress, & stows away in a snap for more room. A 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 favorite

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, 774 reviews

HotTub & Pool 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 favorite

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

4.85 out of 5 average rating, 129 reviews

Entire spacious basement with 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!

Guest favorite

A cozy wooden bunkie is illuminated by string lights, surrounded by trees, creating a serene outdoor setting. A small firepit is visible on a wooden deck, with a few chairs arranged nearby, inviting relaxation and outdoor enjoyment.

Tiny home in Belwood

4.91 out of 5 average rating, 243 reviews

Cedarwood Retreat Bunkie

Stay on a quiet property amongst trees. Enjoy a firepit, cozy private sleeping & bathroom bunkies plus seasonally available outdoor shower (closes Oct 1). In a separate house is where I live & operate Uniquely Pure Studio. IMPORTANT ✨Pack for the cold in winter❄️ Roof & floor insulated but still a glamping style experience. Heaters, blankets, snuggie's & water provided. Wood doors expand/contract with weather so close kind but firm if needed. Leave dishes to us in winter ❄️ No kids or pets

Top guest favorite

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, 131 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.

Guest favorite

The historic log cabin from the 1850s is surrounded by lush greenery. A covered porch with wooden beams invites relaxation, while hanging flower baskets add subtle color. The peaked roof and wooden siding emphasize the cabin's rustic charm in a serene forest setting.

Cabin in Erin

4.95 out of 5 average rating, 187 reviews

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.

Top guest favorite

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, 163 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.

Guest favorite

A charming exterior of the Clayhill Bunkie is presented, featuring a dark blue wooden facade with a steeply pitched roof. Two windows, adorned with flower boxes, flank a central door that is decorated with a natural wreath. Lush greenery surrounds the entrance, enhancing the serene setting.

Guesthouse in Halton Hills

4.94 out of 5 average rating, 128 reviews

The Clayhill Bunkie

Looking for a place to get away that’s semi off-grid or a place that’s kind of like glamping? The Clayhill Bunkie is just the place and minutes from Silvercreek & Terra Cotta Conservation areas, the Credit River, the villages of Glen Williams and Terra Cotta, and the town of Georgetown. Spend your day hiking, cycling, antique hunting, tubing, or site seeing, then order in or grab some take-out and come relax by a roaring fire. Firewood is included, adding great value to your stay.

Top guest favorite

The spacious bedroom features a king bed with a striped blanket and a decorative area rug. Large windows allow natural light, which brightens the neutral walls. French doors lead to an outdoor area, complemented by a seating arrangement and a wooden furniture set.

Place to stay in Mono

4.95 out of 5 average rating, 224 reviews

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.

Top guest favorite

The bedroom features a queen bed dressed in white linens, complemented by a textured blue throw. One nightstand with a red lamp and a decorative pillow adds color. A mirror reflects the room, while soft natural light enters through a nearby window, dressed with light curtains.

Guest suite in Orangeville

4.96 out of 5 average rating, 134 reviews

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

Top guest favorite

A private detached apartment is visible nestled among tall trees and lush greenery. The wooden exterior of the structure blends harmoniously with the natural surroundings. A pathway leads towards the entrance, framed by a vibrant landscape of ferns and colorful shrubs.

Guest suite in Caledon

4.98 out of 5 average rating, 125 reviews

Casa Caledon-Secluded Suite Surrounded by Nature

Take it easy at this unique and tranquil getaway on 3 acres of land The suite is close to conservation areas Cheltenham Badlands, Fork of the Credit and Terra Cotta Bruce trail, golf courses, restaurants, bakeries, butchers, farm produce and city needs are close Each season is wonderful Spring/summer has lush forests, the pond and fire pit Fall walks with the beautiful colours Winter has a white blanket and access to winter sports