Family-friendly vacation rentals in Orangeville

Guesthouse in Orangeville

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.

4.95 out of 5 average rating, 399 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.

Indoor spacesKitchenQuiet

Guesthouse in Orangeville

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.

4.94 out of 5 average rating, 151 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 :)

KitchenIndoor spacesOutdoor spaces

4.84 out of 5 average rating, 104 reviews

The kitchen features modern appliances, including a stainless steel refrigerator, oven, and microwave, arranged around a warm, wooden countertop. White cabinetry complements the neutral walls, while a sleek sink is positioned near the countertop, enhancing functionality in the space.

Condo in Orangeville

Modern Private Suite | Full Kitchen, Self Check-In

Welcome to our fully renovated 700 sq ft, lower-level suite, complete with a full kitchen. Basement suite is accessed through a shared front foyer, private locked door and self check-in via keypad. A 2 min walk to the hospital, and a short drive to arenas and downtown. Ideal for medical stays, hockey families, and anyone looking for quiet. Parking for one car on the driveway (free street parking May-October). Our 5-day cancellation policy ensures your dates are held exclusively for you.

KitchenIndoor spacesAccess

4.95 out of 5 average rating, 349 reviews

A charming two-story cabin is nestled among lush greenery, with a pathway leading to the entrance. Tall trees and well-maintained hedges surround the home, creating a sense of privacy. Soft sunlight illuminates the cabin, enhancing its rustic appeal.

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:) Add a playful Yoga/Functional Movement class or chef's dinner to your stay!

Indoor spacesKitchenDecor

4.95 out of 5 average rating, 160 reviews

An open concept living area showcases large panel doors that fully open to the outdoor deck. Inside, a comfortable seating arrangement is visible, along with a cozy area rug and a neutral color palette. Natural light floods the space, enhancing the connection to nature.

Cottage in Mono

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.

Indoor spacesKitchenAccuracy

4.94 out of 5 average rating, 197 reviews

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

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.

Indoor spacesKitchenNearby

Guest suite in Orangeville

4.92 out of 5 average rating, 884 reviews

Private HotTub & Pool - Headwaters Retreat

Escape to our modern and rustic Queen Suite, with private hot tub right at your door. Relax by the pool, or 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 a quiet escape away. Book now for your ultimate getaway in comfort and nature!

Indoor spacesKitchenHot tub

4.98 out of 5 average rating, 182 reviews

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 Orangeville

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.

FamilyIndoor spacesQuiet

4.99 out of 5 average rating, 424 reviews

A charming stone house is set against a backdrop of lush greenery. The facade features large windows and a welcoming porch. A well-kept lawn leads to the entrance, offering a serene view of the surrounding trees.

Cabin in Arthur

The Stone Heron

Welcome to the Stone Heron, a diamond in the country side!.Check out our insta-gram :thestoneheron. Small stone house completely reno'd!Large master bedroom, gorgeous bathroom and queen bed in aw/game table downstairs a pool table & darts. DVD, TV wii. Entire home is yours to use, its private, nestled into a hillside covered in periwinkle -nature your only neighbour! Large pond walking trails, wildlife, unplug relax and enjoy!Star filled nights amazing sunsets. Pet friendly!

Indoor spacesKitchenHeating

Guesthouse in Halton Hills

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.

4.92 out of 5 average rating, 185 reviews

The Clayhill Bunkie

Semi off-grid bunkie on The Bruce Trail and minutes from Silvercreek & Terra Cotta Cons. areas, the Credit River, Glen Williams, Terra Cotta, & Georgetown. Spend your day hiking, cycling, antique hunting, tubing, or site seeing, then order in or grab take-out and come relax by a fire. 1 basket of wood is included, adding great value. You WILL hear wildlife and farm animals here. Rural property, limited electricity, beautiful views. This is NOT a hotel room.

FamilyKitchenComfort

4.86 out of 5 average rating, 173 reviews

Townhouse in Orangeville

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!

FamilyKitchenLocation

Guest suite in Orangeville

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.

5 out of 5 average rating, 201 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.

Indoor spacesKitchenDecor

Popular amenities for Orangeville family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Guest suite in Elora-Salem

A dining area is featured with a round table surrounded by four sleek chairs. A patterned wallpaper adds texture, while a rack displays hanging clothing. The kitchen includes a wooden countertop and modern appliances, complemented by natural light from nearby windows.

4.97 out of 5 average rating, 145 reviews

The Carlton Elora | Cozy Retreat with Hot Tub

KitchenIndoor spacesAccess

4.89 out of 5 average rating, 460 reviews

A cozy cottage is nestled among vibrant autumn foliage. The front features large windows and a welcoming deck, with outdoor seating visible. Surrounding trees display various shades of yellow and orange, contributing to a serene nature setting.

Cabin in Innisfil

Kempenhaus- Lake Simcoe Cottage & Spa | HOT TUB

FamilyKitchenGetting around

4.96 out of 5 average rating, 195 reviews

Dome in Utopia

Glamping Dome Riverview Utopia

KitchenIndoor spacesGrill

Farm stay in Township Of Southgate

An industrial-style apartment features a spacious open living area with a dark leather couch and a wooden coffee table. A staircase leads to an upper sleeping area, while concrete walls provide a modern backdrop. Natural light enters from nearby windows, enhancing the interior space.

4.86 out of 5 average rating, 220 reviews

Loft Where City Meets Country With Hot Tub

Indoor spacesKitchenBeach

Tiny home in Horning's Mills

A wooden bunkie is set among tall trees, featuring a spacious deck surrounded by a railing. A barbecue unit is positioned on the deck, and a rustic charm is evident in the structure with its natural wood finish and a sloped roof.

4.9 out of 5 average rating, 196 reviews

Pine River Bunkies: Owl’s Roost Off Grid Cabin

Indoor spacesFamilyShared spaces

4.96 out of 5 average rating, 152 reviews

A cozy sitting area is presented with a blue checkered sofa and a striped armchair, adorned with nautical-themed cushions. Light is provided by two lamps on either side, illuminating the artwork and rustic wooden beams above.

Guesthouse in Erin

The Captain's Cottage at Willow Pond

Indoor spacesKitchenPets

4.94 out of 5 average rating, 226 reviews

A luxury tent is set amongst lush greenery, featuring a wooden deck with Muskoka chairs and a private hot tub. A hammock is visible to one side, with a picnic table positioned nearby, all surrounded by trees and natural landscaping.

Farm stay in Elora

Luxury Glamping on Elora Sunflower Farm -Sunflower

Indoor spacesKitchenView

4.89 out of 5 average rating, 105 reviews

Home in St. Jacobs

Boho 4-Bed House Retreat: HotTub, Sauna Oasis &Spa

FamilyKitchenAccess

Family- and pet-friendly home rentals

4.9 out of 5 average rating, 265 reviews

A glamping dome is set amidst a lush green landscape, reflected in a serene pond featuring lily pads and blooming flowers. Towering trees provide a natural backdrop, while a wooden deck extends from the dome, enhancing the outdoor experience.

Dome in East Gwillimbury

Deerleap Glamping Dome

Indoor spacesKitchenWalkability

4.92 out of 5 average rating, 170 reviews

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

Whispering Pines Cabin in Woodland Acres

FamilyIndoor spacesValue

Apartment in Horning's Mills

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.

4.96 out of 5 average rating, 340 reviews

Beautiful Riverside Country Apartment

FamilyIndoor spacesValue

4.86 out of 5 average rating, 159 reviews

A charming wooden Bunkie is nestled among lush greenery. The front porch features a small wooden deck with two red chairs and a round table. Large windows allow natural light to illuminate the interior while the door is framed by a welcoming entry.

Cabin in Caledon East

Bunkie in the Forest

FamilyIndoor spacesCondition

4.86 out of 5 average rating, 260 reviews

Home in Caledon

Studio Apartment

FamilyKitchenValue

4.97 out of 5 average rating, 163 reviews

Cabin in Priceville

Scarlet Yurt Cabin | Cozy Nature Retreat

Indoor spacesKitchenView

4.94 out of 5 average rating, 302 reviews

A spacious living area features a white leather sectional sofa and a circular coffee table on a light rug. The wooden ceiling and walls add warmth, while a staircase leads to an upper level. A dining area is visible in the background, alongside a rustic table.

Cabin in Cambridge

Forest Hideaway

Indoor spacesFamilyBathroom

4.99 out of 5 average rating, 237 reviews

The interior of the cabin features warm wooden walls and a cozy woodstove. Two blue lounge chairs are positioned near a rustic table. Natural light floods through a large window, illuminating the space, while a striped rug adds comfort underfoot.

Tiny home in Schomberg

SNAKE CABIN(rustic, 'off-the-grid')

Indoor spacesKitchenCondition

Family-friendly home rentals with a pool

5 out of 5 average rating, 203 reviews

The exterior of a modern two-story home is displayed, featuring a brick and stone facade. A well-maintained driveway leads to a double garage with decorative doors. Bright flower pots are positioned near the entrance, while lush green landscaping surrounds the property.

Apartment in Newmarket

The Hilton BnB Adult Luxury Suite

Indoor spacesFamilyWifi

4.96 out of 5 average rating, 118 reviews

Home in Erin Mills

Luxurious 2 bdr suite near SQ1, UTM, parking/pool

FamilyIndoor spacesAmenities

Dome in Bradford West Gwillimbury

Vibrant autumn foliage displays shades of yellow and orange surrounding a geodesic dome. A pathway of stone steps leads through a lawn covered in colorful leaves, creating a serene outdoor setting amidst lush greenery.

4.97 out of 5 average rating, 496 reviews

Four season glamping dome under the stars

KitchenIndoor spacesAccuracy

4.91 out of 5 average rating, 278 reviews

Cottage in Innisfil

Utopia villa and spa

FamilyIndoor spacesCheck-in

Guesthouse in Orangeville

4.86 out of 5 average rating, 7 reviews

Ballo - GuestHouse

Sleep qualityValueHospitality

4.97 out of 5 average rating, 222 reviews

Guesthouse in Breslau

House on the Hill

FamilyIndoor spacesCondition

4.95 out of 5 average rating, 106 reviews

A stone fireplace is set into a rustic wall made of various sized natural stones, providing a textured and earthy backdrop. A flat-screen TV is mounted above, and a wooden cabinet is positioned to the left, adding warmth to the living space.

Apartment in Caledon

Separate apartment with pool, on golf course.

FamilyIndoor spacesOutdoor spaces