Family-friendly vacation rentals in Grey Highlands

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Grey Highlands

  • Total vacation rentals

    Explore 1,070 vacation rentals in Grey Highlands

  • Nightly prices starting at

    Grey Highlands vacation rentals start at G$8,361 GYD per night before taxes and fees

  • Verified guest reviews

    Over 60,210 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 430 rentals that welcome pets

  • Vacation rentals with a pool

    380 properties feature pools

  • Rentals with dedicated workspaces

    560 properties have a dedicated workspace

  • Wi-Fi availability

    1,010 of Grey Highlands vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Grey Highlands rentals

  • 4.8 Average rating

    Grey Highlands stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated family-friendly rentals in Grey Highlands

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

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Top guest favorite
The exterior of a charming tiny house is showcased, featuring a rustic wooden design and a welcoming deck. Large windows allow for ample natural light, while a pergola extends over part of the deck, creating a shaded area for outdoor relaxation amidst a lush, green landscape.
Tiny home in Kimberley
4.98 out of 5 average rating, 182 reviews

Hand-Crafted Cabin in Stunning Beaver Valley

Lovingly designed and built tiny house in the heart of the beautiful Beaver Valley. 2 Double beds, small kitchenette, rustic deck & living area with a gorgeous outhouse. The property has extensive edible landscapes & greenhouse filled with seedless grapes & edible perennials. Beautiful views of the escarpment, close to the Bruce Trail & Beaver River access point for canoeing and kayaking. Shop at the achingly charming Kimberley General Store. Close to Blue Mountains, Thornbury & Collingwood

KitchenIndoor spacesNearby

Top guest favorite
Farm stay in Kimberley
4.96 out of 5 average rating, 134 reviews

Valley View Farm Retreat ~ Family, Pets, Hiking

Enjoy this unique 4 bedroom Farm House as a gorgeous space to gather with family or friends. -Ideal location to come together, relax, & connect. -Central heat & AC. -Take in the spectacular views of the Beaver Valley. -Explore the Niagara Escarpment and lookouts of the Bruce Trail. -Relax and read by the fireplace. -5 min walk to our swimming pond with dock & beach -Convenient drive to groceries and local villages. -25 min drive to the Blue Mountains. -Reliable, consistent high speed internet.

Indoor spacesFamilyPool

Top guest favorite
A modern cottage features a stone exterior with a sloped roof, harmoniously blending into the surrounding forest. A cozy propane fireplace is visible on the patio, which overlooks a gently flowing stream bordered by smooth stones and lush greenery.
Cottage in Southgate
4.98 out of 5 average rating, 195 reviews

Luxurious Creek Retreat With Hot Tub

Welcome to this luxury cottage on the water. The perfect place to relax and unwind while listening to the waterfall and babbling brook flowing past only a few feet away. If you're looking for privacy and tranquility along with all the pleasures of a luxury stay then look no further. This property boasts a propane fireplace inside as well as one outside, in-floor heat and A/C. Fully equipped kitchen, two bedrooms with hotel quality mattresses and a bathroom that exudes high-end style and decor.

KitchenIndoor spacesTV

Top guest favorite
The rustic exterior of High Pines Cottage is highlighted by large, floor-to-ceiling windows that allow natural light to fill the interior. Surrounding the cottage, a well-tended garden features a variety of plants, stones, and landscaping elements, adding to the inviting allure of the property.
Chalet in Flesherton
4.97 out of 5 average rating, 102 reviews

Cozy cottage in the woods near trails & waterfalls

High Pines Cottage is a spacious yet cozy, pet friendly retreat. Located on a beautiful 1.8 acre lot that hosts a variety of large pines and other beautiful trees, it offers privacy and relaxation. It is perfect for any season with many activities from hiking to skiing and has a home gym. Whether you are looking to curl up by the fireplace or enjoy the trails with your pup, our cottage offers what you need to unwind or connect with friends and family. Check out Instagr. @high_pines_cottage

FamilyKitchenQuiet

Top guest favorite
Chalet in Meaford
4.97 out of 5 average rating, 138 reviews

Sundance of Blantyre Lodge +Hot Tub +Sauna +Pond

Welcome to Sundance of Blantyre! Step back in time in this historic yet modernized Lodge! This 3600 sq. ft retreat on the Bruce Trail has Breathtaking Valley Views from your own Private Hot Tub & Fire Pit all the Way to Georgian Bay. We invite you to enjoy our truly unique and tranquil getaway with 6 bedrooms + Private Sauna House! With 3 firepits, swimmable/fishing pond, hiking, cross country skiing and snow shoeing + snowmobile/ ATV trail access at your door, Your adventure awaits!

FamilyKitchenCheckout

Top guest favorite
A tranquil cabin is nestled among tall trees in a lush forest. A clear path, lined with smooth stones, leads to the cabin's entrance, which features a welcoming front porch. Sunlight filters through the trees, illuminating the natural surroundings.
Cabin in Kimberley
4.98 out of 5 average rating, 429 reviews

Kimberley Creek Cabin

Kimberley Creek Cabin is located in Kimberley, Ontario on a 2 1/2 acre lot surrounded by an old growth forest with a stream running through the property. If you are looking to connect with nature and you enjoy upscale facilities, then this special vacation spot gives you the best of both worlds. Nightly rate includes HST. We are close to hiking, cycling, canoeing, golfing, winter sports, spas, art studios, and fine dining, or simply relax by the firepit or on one of two private decks.

Indoor spacesFamilyAir conditioning

Guest favorite
A charming A-frame house is set among lush greenery, elevated on a deck that offers outdoor seating. Vibrant pink flowers are visible in the foreground, with a backdrop of tall trees and a clear blue sky. The architecture features large windows allowing for ample natural light.
Cabin in Kimberley
4.96 out of 5 average rating, 102 reviews

Beaver Valley Escape - HotTub & Outdoor Pizza Oven

Beautiful country house on 12 acres, 4 bedrooms and 3 bathrooms. 2 bedrooms are en suite. Vaulted ceilings with light streaming in. Fully stocked kitchen, large hot tub, Weber BBQ, wood burning stove and yoga loft. Beautiful views of the valley. Tranquil setting with gardens and trails out the door. Come and enjoy this area perfect for active families. Minutes from award winning restaurants and the Bruce Trail. Starlink has been installed so internet is fast if you need to connect.

KitchenFamilyNearby

Top guest favorite
A rustic wooden bridge spans a gently flowing stream, surrounded by lush greenery and tall trees. A manicured lawn is visible in the background, featuring multiple seating options. The water reflects the natural landscape, enhancing the serene ambiance of the setting.
Cabin in Kimberley
4.99 out of 5 average rating, 109 reviews

Private Luxury Creekside Cabin with Sauna

Exclusive luxury retreat! Creekside Cabin is the perfect couples escape to nature! This newly renovated gem is nestled in the forest calling you to unwind, refresh and to rejuvenate. Creekside is a fully licensed private property will instantly welcome you with peaceful sounds of cascading streams and waterfalls. Surrounding the beautiful pond, the forest setting is home to an array of wildlife including spotted deer, blue heron and even the beautiful snowy owl casually passing through.

Indoor spacesKitchenSleep quality

Top guest favorite
An open-concept living room and kitchen area is highlighted by a cozy gas fireplace and a cathedral ceiling. Light-colored walls complement the stylish green cabinetry. Two barstools are positioned at the kitchen island, with natural light streaming through the window.
Apartment in Nottawa
5.0 out of 5 average rating, 120 reviews

The Nottawa Nest

Spacious loft apartment, nestled in the heart of Nottawa, a quiet and friendly village just 5min. south of downtown Collingwood and 15min. from Blue Mountain and Wasaga Beach. Enjoy next door the local pub restaurant, cafe, bookstore & LCBO variety store. This beautifully finished getaway has two comfortable bedrooms, laundry room with daybed, dedicated work space, open concept living room & kitchen with cathedral ceiling & gas fireplace. Perfect for two couples, small family or group.

Indoor spacesKitchenNearby

Guest favorite
A hot tub filled with clear water is positioned in the foreground, with steam rising gently. In the background, a cozy seating area surrounds a fire pit, set against a backdrop of lush greenery and a sunset sky.
Guest suite in Kimberley
4.94 out of 5 average rating, 864 reviews

The Post Office Motel & Spa in the ❤️ of Kimberley

*NEW HOT TUB* Located in the center of Kimberley downtown, a scene straight out of a hallmark movie. Watch the seasons come & go while taking in mtn views and soaking in the hot tub as stars line the night sky.Enjoy marshmallows by the 🔥, amidst this whimsical fortress.Walk to the General Store pick up fresh baked goods and breakfast supplies. Then the dinner choice is yours; Hearts Tavern or Justin’s Oven both just steps away. Bruce trail access at the door. The perfect slow down🌿

FamilyKitchenCondition

Guest favorite
Cottage in Flesherton
4.95 out of 5 average rating, 159 reviews

All-Season Cottage on the Lake

An entire cottage all to yourself right on the water of Lake Eugenia in the Grey Highlands. This fully furnished 3-bedroom cottage is equipped with a brand-new kitchen, appliances, wood burning stove, furnace and water heater. You'll also have FREE access to unlimited WiFi, so you can work or stay in touch, when needed. Our cottage is suitable for a great get-away with any group, family or friends who are looking for a peaceful and enjoyable holiday from their busy lives.

FamilyIndoor spacesLocation

Top guest favorite
The log cabin is surrounded by vibrant autumn foliage, with a large front deck and stairs leading to the entrance. The natural wood exterior is complemented by a gabled roof. Softly illuminated lanterns are positioned by the door, enhancing the inviting appearance.
Cabin in Flesherton
4.96 out of 5 average rating, 128 reviews

MapleHaven Cabin @ Lake Eugenia

A rustically elegant log cabin sitting on an acre of beautiful mature maple trees on a quiet dead-end street. Find peace and tranquility in the rustic atmosphere the log cabin setting provides, but enjoy all of the comforts of home. Enjoy 3 bedrooms ,2 baths with a master bedroom that features a coffee bar and covered balcony . Located at Lake Eugenia, in the heart of the scenic Beaver Valley, a 4 seasons playground. Walking distance to public beach/boat launch.

FamilyIndoor spacesLocation

Popular amenities for Grey Highlands family-friendly rentals

Family-friendly home rentals with a hot tub

Family-friendly home rentals with a pool

Guest favorite
Townhouse in Blue Mountain Resort Area
4.89 out of 5 average rating, 162 reviews

Mountain Hideaway | Games, Sauna & Summer Pool

FamilyIndoor spacesHospitality

Guest favorite
A spacious living area features tall windows allowing natural light to fill the room. A large screen TV is mounted above a gas fireplace, surrounded by comfortable seating. Decorative pillows enhance the sectional sofa, and an elegant coffee table sits centrally, adding to the inviting atmosphere.
Townhouse in Blue Mountain Resort Area
4.96 out of 5 average rating, 271 reviews

Après Blue- 2bed2bath w/Pool 6 min walk to village

Indoor spacesKitchenLayout

Top guest favorite
A cozy living area is presented with two sofas and a fabric armchair, arranged around a wooden coffee table. A gas fireplace sits beneath a wall-mounted television. Large windows allow natural light, offering views of the surrounding landscape.
Condo in Blue Mountain Resort Area
4.93 out of 5 average rating, 318 reviews

The Blue Mountain's Dream Escape | Pool | Hot Tub

KitchenIndoor spacesAmenities

Superhost
A spacious seating area features a dark brown leather couch adorned with decorative pillows. Light streams through white, wooden shutters, illuminating the room. A wall-mounted TV and air conditioning unit are visible, along with a bunk bed situated in the background, enhancing the family-friendly atmosphere.
Loft in Blue Mountain Resort Area
4.88 out of 5 average rating, 192 reviews

Fox Ridge | Hot Tub & Shuttle w/ Patio

FamilyKitchenValue

Superhost
Cottage in Meaford
4.91 out of 5 average rating, 140 reviews

Cottage w Heated Pool & Hot Tub Near Blue Mountain

KitchenFamilyCleanliness

Top guest favorite
A cozy living area features a plush sectional couch and a wooden coffee table. Large windows provide views of the golf course, allowing natural light to brighten the space. A modern fireplace adds a welcoming touch, complemented by soft curtains and decorative wall accents.
Condo in Blue Mountain Resort Area
4.94 out of 5 average rating, 657 reviews

Blue Vista | Pool/Hot Tub/Shuttle/WalkToBlue

FamilyKitchenOutdoor spaces

Guest favorite
An open-concept living area showcases a modern kitchen with stainless steel appliances and a large island. A cozy seating area features a dark sofa and an armchair, positioned near a stone fireplace. Natural light fills the space through multiple windows.
Condo in Blue Mountain Resort Area
4.92 out of 5 average rating, 201 reviews

Blue Mountain condo in Historic Snowbridge

FamilyKitchenCheckout

Guest favorite
A private outdoor pool surrounded by a spacious patio is showcased, featuring colorful lounge chairs in shades of pink. Lush trees and greenery border the area, contributing to a serene setting under clear blue skies.
Chalet in Blue Mountain Resort Area
4.85 out of 5 average rating, 104 reviews

7BR Chalet | Hot Tub + Seasonal Heated Pool

Indoor spacesFamilyCheckout

When is the best time to visit Grey Highlands?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$49,332 GYDG$52,886 GYDG$42,225 GYDG$34,491 GYDG$36,372 GYDG$36,999 GYDG$44,734 GYDG$49,123 GYDG$34,700 GYDG$36,163 GYDG$34,073 GYDG$55,813 GYD
Avg. temp-7°C-6°C-1°C6°C12°C17°C20°C19°C15°C9°C3°C-3°C

Destinations to explore