Family-friendly holiday rentals in Halton Hills

4.97 out of 5 average rating, 381 reviews

A chestnut horse stands near a wooden fence, gazing towards the camera. The background features a hazy sunrise, casting a warm glow over the field and creating a tranquil atmosphere.

Tiny home in Action

Farmview Sunrise Cabin located at Molinaro Farm

Welcome to our Farmview Sunrise tiny cabin that is nestled in the middle of our private oasis located in Acton ON. Our 50 acre farm has spectacular views from every direction. Our horses, sheep, swans, ducks, chickens and miniature goats are here to greet you as well. This unique space will allow you to enjoy the beautiful outdoors during the day and a cozy warm space in the evenings. We offer a complementary breakfast for our guests. Our in house chef can also accommodate vegan/plant based

FamilyIndoor spacesAir conditioning

4.97 out of 5 average rating, 173 reviews

A single-story bungalow is shown at dusk, highlighting a welcoming exterior. Snow blankets the ground, while warm light spills from the windows, hinting at a cozy interior. The driveway leads to a garage on the right, surrounded by bare trees against a twilight sky.

Apartment in Georgetown

★Hidden Gem❤️City, off Mn Strip! PVT/LUXRY Suite ★

Rexway House is a luxurious main FLR, newly renovated & furnished 3 bedroom Apartment/suite bungalow, accommodate's 4. (Located in the Heart of the City), BIG Front & Back yard's, with sunrise/sunset views.* FREE* 4 Car driveway parking Dairy Queen /Mc Donald's, Just Step's away at the Top of the Street, and minute's walk to All Major Supermarket's, WINE/BEER store's, Shopping Mall, pub's/entertainment, eatery's, European bakeries, Convenience Store's, and Fast Food place's, PLUS much more.

KitchenIndoor spacesHiking

4.97 out of 5 average rating, 277 reviews

Dome in Burlington

Jungle Dome on a Farm! Animal Lovers Dream!

Jungle Dome Farm Stay in Burlington! Be completely immersed in farm life and all that it entails while staying in our 500 square foot geodesic dome “glamping” greenhouse dwelling! Complete with a fish and turtle pond and filled to the brim with tropical plants! Designed as a tropical vacation getaway when you can’t get away to the tropics! Situated on a 5 acre animal farm where guests can experience farm life with goats, horses, highland cows, sheep, pigs and poultry. An Animal Lovers Dream!

KitchenFamilyBeach

4.85 out of 5 average rating, 159 reviews

An aerial view captures the waterfront trailer set against lush greenery, with a private deck featuring seating arrangements. Nearby, two kayaks await by the water, and a fire pit is surrounded by logs. The tranquil lake reflects the surrounding foliage.

Tiny home in Action

Lakefront 1 bedroom tiny home

Reconnect with nature at this unforgettable escape. Enjoy a wonderful stay in our lovely waterfront trailer located on Breezes Trailer park. It is a private quiet trailer park with 15 acres of nature and private access to Fairy Lake (Acton). Trailer is suitable for couple or small family. It is suited to people looking to relax and enjoy the scenery, explore the lake on kayak, exercise and explore on water bikes, fishing in the lake, enjoy some outdoor movies or campfire or under the stars.

FamilyIndoor spacesCondition

4.8 out of 5 average rating, 142 reviews

A modern living space is presented with sleek furniture including a dark sectional sofa and a round dining table. A large flat-screen TV is mounted on a wall, while an electric fireplace is integrated into the media console. A stainless steel fridge is visible in the kitchen area.

Guest suite in Milton

Amna & Raza's Cozy Nest

Enjoy a cozy and bright 2-bedroom basement apartment with a separate entrance. Featuring a full kitchen, electric fireplace, TV, free WiFi, and a dedicated parking. One bedroom with a double bed, the other with a pull-out bed. Family-friendly, peaceful, and newly renovated. Just 5 mins walk to grocery, pharmacy, park, and food spots. 10 mins walk to a 24/7 gas station and convenience store. 10 minutes drive to Go station. EV charger available on request. Perfect for short or extended stays!

FamilyIndoor spacesParks

4.93 out of 5 average rating, 120 reviews

An open living area features a cozy seating arrangement with a sofa and a day bed, which can extend to a king bed. A modern kitchen with sleek cabinetry is visible alongside a small dining table. A fireplace adds an element of warmth to the space.

Bungalow in Georgetown

Modern Stay • Prime Location • Double Parking

Newly renovated, 1-bedroom walkout basement apartment! ✅ 750 sq. ft. of open space with large windows, making it bright and airy Cozy living area with: ✅ Sofa ✅ Day bed that extends to a king bed ✅ Fireplace ✅ Smart TV Modern kitchen equipped with: ✅ Dishwasher ✅ Microwave ✅ Washer and dryer ✅ Coffee machine ✅ Oven, toaster, etc. ✅ Outdoor area with a patio and BBQ ✅ 2 Parking Spots on driveway Perfect for family vacations or business trips! 😊

Indoor spacesKitchenComfort

Shipping container in Puslinch

The exterior of a modern, dark-toned tiny home is framed by trees. A private dock with Adirondack chairs sits by the water, reflecting the structure's warm lights. The tranquil setting is enhanced by the surrounding natural landscape and evening ambiance.

Wildwood Tiny Home Escape with Wood Fired Sauna

Welcome to an absolutely unique converted shipping container – Wildwood Tiny Home! This converted shipping container has a big personality! If you and your guests are looking for luxury, nature, peace, serenity, and a chance to escape the city – this getaway is perfect for you! At Wildwood Tiny Home, you can fill your time with hanging out on your own private beach & waterfront dock, enjoying your firepit, beach volleyball, horseshoes, cornhole, badminton, board games, and many more!

KitchenFamilyBeach

4.99 out of 5 average rating, 128 reviews

4.9 out of 5 average rating, 221 reviews

Apartment in Georgetown

The Jack Daniels Suite.

Mr. Daniels is out on a whiskey run. This western themed unit, with the top quality accommodations. This warm cosy second floor (NOT basement) bachelor suit is equipped with everything necessary. Based on a western theme this will take you back to the wild Wild West. Located in the heart of the village of Georgetown, this unit steps away from the Main Street where you will find many restaurants, pubs, cafes and more. Come enjoy the peace and tranquillity of the old village.

KitchenIndoor spacesHospitality

4.8 out of 5 average rating, 171 reviews

A brick exterior home is set against a bright blue sky, featuring a manicured front lawn with green grass and white flowers. Large windows allow natural light to illuminate the entrance, where a welcoming white door is positioned. A tree provides shade, enhancing the outdoor space.

Home in Georgetown

Halton Hills Hideaway_Private Suite

🌿 Halton Hills Hideaway – Cozy Basement Suite Near Downtown Georgetown ✨ What You’ll Love: 🚪 Private Basement Suite – Separate entrance & no shared areas 🛏️ Queen Bed – Comfy and perfect for solo travelers or couples 🌳 Garden Views – Enjoy calming green views from your lookout window 🧼 Clean & Cozy – Thoughtfully prepared for a peaceful stay 🏘️ Charming Neighborhood – Quiet, friendly, and safe 🔍 Check the amenities section for full details—we’d love to host you!

KitchenIndoor spacesSleep quality

Guesthouse in Halton Hills

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.

Indoor spacesKitchenLong stay

4.92 out of 5 average rating, 197 reviews

4.94 out of 5 average rating, 108 reviews

A bright living area features high ceilings and large windows, allowing natural light to illuminate the space. Two comfortable sofas are positioned around a central coffee table, which holds a decorative glass tray and fresh flowers. A soft area rug covers the wooden floor.

Apartment in Georgetown

Stylish In-Law Suite in Georgetown

🏡 In-Law Suite with private entrance, high ceilings, and large windows filled with natural light. Relax on a comfortable King bed, enjoy Netflix, and free WiFi. 🌳 Located on 1 acre in Georgetown, just minutes from restaurants & pubs. Plenty of on-site parking. Faces Main Street, so some traffic noise may be heard. 👨‍👩‍👧 Accommodates 2 adults or 2 adults + 1 child (no 3 adults). ✨ Cleanliness is our top priority — we aim to make every guest happy!

KitchenFamilyDecor

4.76 out of 5 average rating, 119 reviews

A comfortable sleeping area is furnished with a queen bed, dressed in a patterned blue and white blanket. A cozy sofa is positioned nearby. Warm lighting is provided by a wall-mounted fixture, and a piece of artwork featuring a tree is displayed above the bed.

Home in Milton

Spacious, Pet Friendly Basement Apartment

Quiet, pet-friendly private basement suite designed for comfort and easy stays. Features a queen bed, sofa bed, fully equipped kitchen, dining area, in-suite laundry, free Wi-Fi, and complimentary coffee & tea. Guests enjoy a shared backyard with a seasonal pool and barbecue in summer. Loved for its privacy and comfort while being steps from a park, grocery store, pharmacy, bank, and nearby restaurants—perfect for short or extended stays.

Indoor spacesKitchenCheck-in

Popular amenities for Halton Hills family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 187 reviews

The serene backyard features a heated saltwater pool surrounded by a stone deck, bordered by lush greenery and blooming trees. A patio area includes outdoor seating and a grill, while large windows overlook the pool, enhancing natural light in the adjacent indoor space.

Home in The Beaches

Luxury 4BR: 365 Days Open- Heated Pool & Hot Tub

KitchenIndoor spacesNearby

4.92 out of 5 average rating, 188 reviews

The hillside villa features multiple levels with large windows offering expansive views. Smooth wooden decks are visible, surrounded by greenery, while a staircase leads to the entry. Reflective glass accents enhance the modern design, blending harmoniously with the natural surroundings.

Villa in Burlington

Waterfront Hillside Villa

FamilyKitchenCheck-in

Guesthouse in Mississauga

A serene backyard is highlighted by a clear swimming pool surrounded by natural stone coping. Comfortable seating arrangements with dark wicker chairs and a sleek table are positioned nearby, offering a relaxing spot. Lush greenery frames the area, providing a peaceful atmosphere.

“CasaDeLeon”- Modern and cozy Lakeview guesthouse

Indoor spacesFamilyCheck-in

4.89 out of 5 average rating, 116 reviews

4.88 out of 5 average rating, 113 reviews

A spacious living room is highlighted by tall wooden ceilings and large windows that invite ample natural light. Two comfortable sofas face each other over a coffee table, with a patterned area rug underfoot. A small fireplace and colorful stained glass add character to the warm design.

Barn in Milton

Five Star Hayloft Suite

KitchenFamilyLayout

4.92 out of 5 average rating, 112 reviews

A light-filled living area features a plush, beige sofa and armchairs arranged around a coffee table. A mirrored wall decoration reflects light, while a decorative chandelier hangs above. The space leads to a staircase and an entrance door with a decorative mirror nearby.

Home in Waterdown

Ninos Place

FamilyIndoor spacesCleanliness

4.99 out of 5 average rating, 187 reviews

Farm stay in Lincoln

Lakefront Farm | Hot Tub | Fire Pit | Beach Access

FamilyKitchenDecor

4.9 out of 5 average rating, 170 reviews

A modern condominium building is showcased from a street view, highlighting two tall, sleek towers with an expansive glass façade. The ground level features a multi-story section with large windows and contemporary architectural elements, set against a clear blue sky.

Condo in Mississauga

Beautiful & Cozy 2Bed 2Bath Condo Steps to Square1

Indoor spacesKitchenLocation

4.95 out of 5 average rating, 217 reviews

A welcoming porch features a blue exterior with white trim, adorned by potted plants and lush greenery. Rocking chairs are positioned on the porch, providing a comfortable space to relax. The pathway is lined with stones, leading from the driveway to the entrance.

Apartment in Ariss

Rural Retreat, near to Elora

FamilyKitchenHeating

Family- and pet-friendly home rentals

4.94 out of 5 average rating, 315 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 spacesFamilyHiking

4.91 out of 5 average rating, 629 reviews

Guesthouse in Guelph

Sweet Studio Cottage ~Spacious Yard ~Nature Haven

KitchenIndoor spacesSleep quality

4.95 out of 5 average rating, 180 reviews

The rustic beach house is surrounded by greenery, featuring wooden siding and a welcoming porch. A separate structure is visible nearby, both enhancing the tranquil setting. The clear blue sky adds to the serene atmosphere of the property.

Cabin in Erin

Rustic Cabin on Private Pond

KitchenFamilyPool

4.91 out of 5 average rating, 110 reviews

An open-concept living area features a sleek electric fireplace beneath a mounted Smart TV. Two round tables with colorful chairs provide seating, while natural light enters through windows adorned with elegant coverings. A modern coffee table sits in front, completing the cozy ambiance.

Home in Milton

Spacious 2 BR apartment | Glen Eden Ski

FamilyIndoor spacesGetting around

4.99 out of 5 average rating, 113 reviews

Cabin in Guelph/Eramosa

Fern Hill Cabin

KitchenIndoor spacesAccuracy

4.73 out of 5 average rating, 178 reviews

An open-concept living space features a leather couch and an armchair, with a coffee table positioned nearby. A light wood kitchen island provides seating with two yellow stools. Natural light enters through two windows, illuminating the modern decor and warm wood flooring.

Apartment in Milton

Studio Apt in Milton Dorset Park

Indoor spacesFamilyLayout

4.92 out of 5 average rating, 230 reviews

Two brown horses are depicted in a snow-covered outdoor setting, closely positioned with their noses touching. Flakes of snow gently fall around them, creating a serene winter scene, while a house and snow-covered trees are subtly blurred in the background.

Bungalow in Hamilton

Horse Ranch with Hot tub

KitchenFamilyQuiet

4.9 out of 5 average rating, 157 reviews

A cozy cabin interior features wooden walls and a lofted sleeping area with a patterned mattress. A black futon is positioned on the ground floor, complemented by a textured area rug. A compact kitchenette area is present, along with a sleek electric heater.

Tiny home in Erin

Bright and Cozy Tiny Pine House

KitchenFamilyView

Family-friendly home rentals with a pool

4.99 out of 5 average rating, 203 reviews

The exterior of a cabin is depicted, featuring wooden siding and a stone base. A small wreath decorates the entrance, which is flanked by a snow-covered landscape. Tall trees stand in the background, hinting at the surrounding nature.

Cabin in Hamilton

The Fox's Retreat - A Cozy Cabin for Two

KitchenIndoor spacesParks

4.96 out of 5 average rating, 123 reviews

Home in Erin Mills

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

KitchenFamilyBackyard

4.95 out of 5 average rating, 356 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)

KitchenIndoor spacesAccess

Guest suite in Mississauga

Full apt on Upper floor near HWY - S Mississauga

Indoor spacesFamilyAmenities

4.92 out of 5 average rating, 174 reviews

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.

Sunny Pines Farm Studio Tennis Court/Bruce Trail

KitchenFamilyComfort

4.96 out of 5 average rating, 404 reviews

4.88 out of 5 average rating, 137 reviews

A serene view of the villa is captured from the edge of the natural spring-fed pond, showcasing its spacious, multi-level design. Surrounding greenery, including trees and landscaped gardens, adds to the tranquility of the setting. Fluffy clouds drift across a bright blue sky.

Villa in Cambridge

Luxury Villa for Accommodation

Indoor spacesFamilyComfort

5.0 out of 5 average rating, 126 reviews

A backyard seating area is viewed, featuring a dark outdoor sectional couch with a black coffee table placed on a striped rug. Surrounding the heated saltwater pool are lounge chairs and lush greenery, creating a serene outdoor space.

Guesthouse in Brampton

Bright and Airy Guest Suite with Pool

Indoor spacesFamilyCleanliness