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Family-friendly vacation rentals in Whitchurch-Stouffville

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Whitchurch-Stouffville

  • Total vacation rentals

    Explore 60 vacation rentals in Whitchurch-Stouffville

  • Nightly prices starting at

    Whitchurch-Stouffville vacation rentals start at ﺩ.ﺇ 110 per night before taxes and fees

  • Verified guest reviews

    Over 1,480 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Whitchurch-Stouffville vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Whitchurch-Stouffville rentals

  • 4.8 Average rating

    Whitchurch-Stouffville stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated family-friendly rentals in Whitchurch-Stouffville

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

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Top guest favorite
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.
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...

KitchenFamilySolo travel

4.97 out of 5 average rating, 503 reviews
Top guest favorite
A charming cabin is nestled among tall evergreen trees, surrounded by well-maintained landscaping. Stone steps lead to the entrance, illuminated softly by exterior lights. The lush green lawn flows gently, creating a serene outdoor setting.
Cabin in Whitchurch-Stouffville

Lakefront getaway for two on Musselman's Lake

An amazing getaway space for two and your dog on beautiful Musselman's Lake, close to Toronto but feels like you're in the Muskokas. This rustic designer one-bedroom cabin is the original attached cottage that our house grew from. Sit at the dock or on your patio to watch the spectacular sunsets. Have a coffee in the backyard and watch the sunrise over 160 acres of trails out your back door. This is your retreat with high-speed internet, full-size kitchen & dining area to enjoy cottage life.

KitchenIndoor spacesHiking

4.99 out of 5 average rating, 146 reviews
Guest favorite
A covered patio area features a hot tub alongside a glass-topped table with comfortable seating. The peaceful lakeside view showcases expansive green space and a row of chairs positioned along the shore, framed by trees lining the property.
Cottage in Georgina

Sunset Shores Lakehouse- Hot Tub, Wet Bar & Games

Welcome to Sunset Shores Lakehouse! Nestled in a tranquil bay on the shores of Lake Simcoe, this spacious family lake house is the perfect escape in all 4 seasons with many indoor and outdoor activities to enjoy! This peaceful waterfront retreat boasts 4 bedrooms + Wet Bar + Patio Oasis with lakeside Fire Pit + 6 person Hot Tub overlooking the lake and spectacular daily sunsets and sunrises you wont want to miss! Only 1 hour from Toronto and close to many Georgina attractions and adventures!

Indoor spacesFamilyAccuracy

4.96 out of 5 average rating, 106 reviews
Top guest favorite
Cottage in Georgina

Resort-Style Luxury Waterfront Cottage

Experience luxury at our 5-star, Superhost-rated waterfront cottage on Lake Simcoe, just 80 KM from Toronto! A guest favorite, it offers breathtaking sunsets and sunrises from the living room and loft. Relax on the sandy beach with waist-deep waters, and enjoy the patio, BBQ, bar, lounge, kayaking, and fishing. With a fully equipped kitchen, 3 bedrooms, and 2 bathrooms, it comfortably accommodates up to 8 guests. Book your dream getaway today for the perfect blend of relaxation and adventure!

KitchenFamilyAmenities

4.96 out of 5 average rating, 144 reviews
Top guest favorite
A spacious living area features a variety of seating options, including a cozy couch and rocking chairs. Large windows allow natural light to enter, illuminating the lush indoor plants. Decorative rugs and artwork add character to the eclectic decor, creating a relaxed atmosphere.
Farm stay in Uxbridge

Private Loft w Sauna, Fireplace, Wi-Fi & Projector

Welcome to the LOFT - A private, eclectically designed spa-inspired unique stay in the historic Webb Schoolhouse, less than an hour from Toronto. Featured in TORONTO LIFE, this private loft includes your own sauna, unique hanging bed, wood stove, kitchenette and is filled with art, and huge tropical plants as well as a projector & giant screen for epic movie nights. Relax and recharge, roam the grounds and enjoy the beautiful outdoor spaces, the permaculture farm, animals, and fire pit.

Indoor spacesKitchenAccuracy

4.98 out of 5 average rating, 365 reviews
Guest favorite
A modern kitchen space is showcased, featuring white cabinetry and a sleek red refrigerator. Essential appliances, including an oven and microwave, are easily accessible. The area includes a dining table, and the light tile flooring reflects the bright ceiling lights, creating an open and inviting atmosphere.
Apartment in Stouffville

New Contemporary Comfort: Your Stylish Retreat

Welcome to brand new 1 Bedroom, 1 Bathroom and Sofa Bed located in quiet neighbourhood. This private unit is equipped with queen size bed, kitchen, full bathroom and access is available through separate entrance. It is fully inclusive of everything you might need, such as a hot water kettle, microwave, oven, stove, dishes and silverware, and coffee maker. Access to downtown Toronto is only 40 min drive. Located near 407 ETR. 10 min to downtown Stouffville with all amenities nearby.

FamilyIndoor spacesBathroom

4.89 out of 5 average rating, 158 reviews
Guest favorite
An open living area is visible, featuring a dining table set with plates and utensils. The kitchen area displays modern appliances against a patterned backsplash. Natural light brightens the space, highlighting the wood-like flooring and neutral walls.
Apartment in Stouffville

New Stylish/Cozy Getaway with Home Office Retreat

Welcome to this cozy basement apartment, combining the comfort of a 1-bedroom layout with the added convenience of a separate office space. As you step inside, you'll find a well-designed living area that seamlessly integrates with the kitchen creating an open and inviting atmosphere. Located in the heart of Stouffville, Ontario, close to all amenities such as Highway 404/407, Stouffville GO, Musselman's Lake, golf courses, hiking trails, grocery stores, bars, and restaurants.

Indoor spacesFamilyParks

4.91 out of 5 average rating, 103 reviews
Guest favorite
A wooden dining table is set with plates, bowls, and glasses arranged neatly along a light-colored table runner. A framed artwork depicting kitchen elements decorates the wall above. Two chairs are positioned at the table, creating a comfortable dining area.
Apartment in Whitchurch-Stouffville

Lucy's Place: Country living near the city

License #PRSTR20241573 Private apartment, self check-in. A cozy and comfortable space with Kitchenette, Ensuite/3 piece bathroom, Queen size bed, Pull out couch and enclosed laundry room. Free parking, 3 Minutes to Hwy 404 or Bloomington Train/Bus station. Spacious backyard and relaxing walks around the quiet and picturesque neighborhood . Immerse yourself in Canadian nature. Minutes to Golf Courses, Hiking Trails, Lakes, Wineries, Skiing (Lakeridge) is 1/2 hr. away.

FamilyKitchenOutdoor spaces

4.88 out of 5 average rating, 148 reviews
Guest favorite
Dome in Zephyr

Glass Dome - Sleep Under The Stars- Free Sundays

Discover this new, stunning 22ft Glass Geodesic Dome nestled in the heart of Uxbridge. Imagine waking up surrounded by 360-degree panoramic views of the natural landscape Please note... its FULL WEEKEND STAYS ONLY - BOOK FRIDAY AND SATURDAY-SUNDAY IS FREE. This allows guests to fully enjoy their Sunday without feeling rushed to check out at 11am. Enjoy all day Sunday with option of staying the evening. 8X12 BUNKIE NOW AVAIL. SLEEPS 4 ( 2 bunk beds) $100 flat fee

Indoor spacesKitchenNearby

4.92 out of 5 average rating, 207 reviews
Superhost
The geodesic dome features a modern white exterior, set against a backdrop of trees. A wooden deck extends from the dome, leading to a covered gazebo, with a pathway of wood chips guiding the approach. Soft sunlight filters through the branches, creating a serene atmosphere.
Dome in Uxbridge

The Bubble Glamping Dome

Escape to a luxury geodesic dome on our scenic farm, nestled at the edge of the forest. Fully equipped with heating, cooling, a private washroom, deck, and hot tub, it’s the perfect blend of comfort and nature. Explore the farm, meet our sheep, chickens, and livestock guardian dog, or hike over 100 acres of connected regional forest. Whether you’re relaxing under the stars or adventuring outdoors, this unique glamping retreat promises an unforgettable experience.

KitchenIndoor spacesWifi

4.86 out of 5 average rating, 156 reviews
Guest favorite
A cozy living area features two brown sofas adorned with colorful cushions. Soft lighting is provided by two lamps flanking the seating. A vibrant artwork hangs on the wall, and light-colored curtains frame the window, contributing to the welcoming atmosphere.
Farm stay in Whitchurch-Stouffville

Orchard cottage, experience the farm in the city

Beautiful country home nestled in an apple orchard surrounded by nature with private access to walking forest trails and set back off the road with beautiful idyllic views. Close to highway 404 and to all amenities-Walmart, Best Buy, etc. 45 min to downtown Toronto. Property has friendly dogs. **discount for 5 guests or more on a long-term stay. Response time up to 3 hours. Town of Stouffville appoved short-term rental permit # is PRSTR20250480

KitchenIndoor spacesPets

4.82 out of 5 average rating, 308 reviews
Guest favorite
Cottage in Innisfil

Utopia villa and spa

✨ Welcome to Utopia Villa & Spa — a private retreat with 3 bedrooms & 2 bathrooms, thoughtfully designed for comfort and connection. Enjoy a seasonal outdoor pool, year-round hot tub, sauna, game room, and cozy spaces for family and friends. 🏡🤍 Just 7 minutes from the beach, with a fresh seasonal look every visit. Ready for your next getaway? Book Utopia today and make memories that last! ✨

FamilyKitchenHot tub

4.91 out of 5 average rating, 291 reviews

Popular amenities for Whitchurch-Stouffville family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favorite
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

FamilyKitchenCondition

4.99 out of 5 average rating, 187 reviews
Superhost
Home in East Gwillimbury

Animal Sanctuary 10 Acres W/Trails/Sauna/Hottub

Indoor spacesKitchenBathroom

4.86 out of 5 average rating, 125 reviews
Superhost
A bright sunroom is showcased with a glass ceiling and walls, providing expansive views of the surrounding nature. A glass dining table is surrounded by black chairs, resting on a soft area rug. The space offers a connection to the outdoors while remaining sheltered.
Home in Scarborough

Ravine Paradise ! heated pool and hot tub!

KitchenFamilyWalkability

4.92 out of 5 average rating, 125 reviews
Guest favorite
A cozy living area features a brick fireplace with a warm flame, complemented by soft lighting from decorative lanterns. A coffee table is adorned with candles and a chilled bottle of champagne, while comfortable seating invites relaxation.
Guest suite in Pickering

* HOT TUB* Guest Suite - Minutes to the Beach!

KitchenFamilyAmenities

4.88 out of 5 average rating, 826 reviews
Top guest favorite
Dome in Utopia

Glamping Dome Riverview Utopia

FamilyKitchenWalkability

4.96 out of 5 average rating, 207 reviews
Guest favorite
A private outdoor space features a hot tub positioned beside a blue swimming pool. Surrounding amenities include a charcoal grill, dining table, and lounge chairs set on a wooden deck, with trees providing natural shade and decorative lighting enhancing the evening atmosphere.
Home in Toronto

Toronto Pool Retreat

KitchenIndoor spacesHot tub

4.86 out of 5 average rating, 111 reviews
Top guest favorite
The exterior of a modern home is highlighted at sunset, showcasing large windows that reflect warm interior lighting. A spacious backyard features green grass, a dining area under a gazebo, and a hot tub on the deck, creating an inviting outdoor space.
Home in Barrie

Waterfront Home, City/Sunset View & Steps to Beach

FamilyIndoor spacesOutdoor spaces

4.98 out of 5 average rating, 161 reviews
Top guest favorite
A spacious lake house exterior is set against a cloudy sky, featuring large windows that allow natural light to enter. The surrounding yard is adorned with fallen leaves, while a deck with outdoor furniture and a hot tub enhances the outdoor space.
Cottage in Innisfil

Spacious family cottage 45 mins from GTA!

FamilyKitchenAir conditioning

4.88 out of 5 average rating, 166 reviews

Family- and pet-friendly home rentals

Guest favorite
A comfortable seating area is presented with two light-colored armchairs, each adorned with decorative pillows. A low, round coffee table features a small vase of flowers. A floor lamp stands beside the seating area, and natural light streams in through a large window.
Townhouse in Markham

*BRAND NEW*Perfect 4 BR Townhouse Markham *Sleep 8

Indoor spacesKitchenParking

4.89 out of 5 average rating, 146 reviews
Guest favorite
A cozy living and dining area features a wooden dining table set with plates and glassware. Two plush sofas surround a glass coffee table in front of a television, while bright yellow flowers add a pop of color to the space. Light-colored walls enhance the inviting atmosphere.
Apartment in Markham

Spacious 2BD 3-6 ppl homestyle BSMT mansion with window basement 130sqm

KitchenFamilyDecor

4.86 out of 5 average rating, 545 reviews
Guest favorite
The exterior of the house displays a stone facade, framed by trees and greenery. A large deck extends from the structure, featuring outdoor seating and a BBQ setup. Nearby, a driveway accommodates several vehicles, with spacious lawn surrounding the property.
Cottage in Georgina

Pearl by Lake Simcoe - with sauna and steam room

Indoor spacesKitchenOutdoor spaces

4.92 out of 5 average rating, 209 reviews
Guest favorite
Guest suite in Innisfil

Beautiful 2BR Apt | Playground + Fire Pit + BBQ

KitchenFamilyWalkability

4.94 out of 5 average rating, 187 reviews
Guest favorite
A tree house is nestled among tall trees, featuring a wooden structure with a balcony and staircase. Soft sunlight filters through the branches, highlighting the natural wood finish and the serene forest surroundings.
Treehouse in Port Perry

Treehouse on private, isolated forest (300 acres)

KitchenIndoor spacesComfort

4.98 out of 5 average rating, 567 reviews
Top guest favorite
A spacious dining area features a large wooden table surrounded by black chairs. A clock with a white face is mounted on the wall, and natural light fills the room through large windows. A view into the living area is visible in the background.
Home in Bond Head

3BR Spacious Home - KING BED

Indoor spacesFamilyHospitality

4.97 out of 5 average rating, 116 reviews
Guest favorite
A spacious backyard features a fire pit surrounded by four adirondack chairs. The cottage showcases large windows and a deck with outdoor dining furniture and an umbrella. Two kayaks are stored nearby, adding to the lakefront atmosphere.
Home in Kawartha Lakes

Cozy Lakeside Cottage on Lake Scugog

FamilyKitchenPets

4.93 out of 5 average rating, 141 reviews
Superhost
An outdoor seating area features a circular arrangement of comfortable furniture, including a low table and spacious couches with light-colored cushions. Black wooden chairs provide additional seating. The background shows a grassy area leading to the water, with trees and a trampoline visible in the distance.
Cottage in Gilford

Lake Side Manor With Games Room

FamilyIndoor spacesValue

4.88 out of 5 average rating, 100 reviews

Family-friendly home rentals with a pool

Guest favorite
The exterior view of the two-story house is framed by lush trees, showcasing large windows that allow natural light to filter inside. A balcony extends from the second floor, providing outdoor space. The structure features a blend of wood and siding materials.
Home in Uxbridge

The Ridge Roost - Uxbridge Township

Indoor spacesFamilyHiking

4.86 out of 5 average rating, 103 reviews
Top guest favorite
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

FamilyKitchenPool

5.0 out of 5 average rating, 206 reviews
Top guest favorite
An aerial view of the rustic chalet reveals a warm wooden exterior complemented by brick accents. A fenced-in yard features a heated, welcoming saltwater pool. Two cars are parked in the driveway, and greenery from surrounding trees enhances the serene atmosphere.
Guesthouse in Barrie

Warm rustic luxury chalet near lake and trails

Indoor spacesKitchenGetting around

4.98 out of 5 average rating, 105 reviews
Superhost
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.
Guesthouse in Mississauga

“CasaDeLeon”- Modern and cozy Lakeview guesthouse

Indoor spacesKitchenLocation

4.89 out of 5 average rating, 116 reviews
Top guest favorite
A swimming pool is featured in a serene outdoor space, surrounded by lush greenery and tall trees. The circular pool is complemented by a stone wall background. A shaded seating area with a table and chairs is nearby, promoting relaxation and enjoyment.
Home in Don Mills

Casa Meya - Toronto Poolhouse Villa

FamilyKitchenParking

4.91 out of 5 average rating, 106 reviews
Superhost
The entrance features double doors in a dark finish, adorned with elegant seasonal wreaths. Flanking the doors are decorative wall art pieces. A small bistro table with two chairs is positioned on a stone patio, complemented by potted snake plants and decorative pumpkins.
Home in Barrie

Luxurious 4BDRM-King Bed-Barrie-near Snow Resorts

KitchenIndoor spacesQuiet

4.9 out of 5 average rating, 145 reviews
Guest favorite
Camper/RV in Lisle

Givi’s Cozy Camper: Warm & Welcoming

FamilyKitchenTV

4.92 out of 5 average rating, 128 reviews
Top guest favorite
Condo in Innisfil

Stunning 1BR w Pool ~ Free Parking & Self Check-In

FamilyKitchenCheckout

4.98 out of 5 average rating, 131 reviews

When is the best time to visit Whitchurch-Stouffville?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 477ﺩ.ﺇ 386ﺩ.ﺇ 430ﺩ.ﺇ 455ﺩ.ﺇ 555ﺩ.ﺇ 602ﺩ.ﺇ 580ﺩ.ﺇ 544ﺩ.ﺇ 474ﺩ.ﺇ 474ﺩ.ﺇ 474ﺩ.ﺇ 477
Avg. temp-3°C-3°C2°C8°C14°C20°C23°C22°C18°C11°C5°C0°C

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