Family-friendly vacation rentals in Grey Highlands

4.98 out of 5 average rating, 181 reviews

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

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

Indoor spacesFamilyWifi

4.95 out of 5 average rating, 131 reviews

Farm stay in Kimberley

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 spacesFamilyBackyard

4.98 out of 5 average rating, 193 reviews

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

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.

FamilyKitchenLayout

4.97 out of 5 average rating, 100 reviews

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

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

Indoor spacesFamilyComfort

4.82 out of 5 average rating, 125 reviews

A wooden cabin is set against a backdrop of greenery, featuring large glass windows that invite natural light indoors. The structure displays a combination of rustic wooden siding and a red-painted section, while the landscaping is dotted with small plants and rocks.

Chalet in Flesherton

The Red House – Private Wooded Oasis & Hot Tub

Unplug in our private 3-acre forest retreat. Wake up in a king bed, brew coffee in the fully-stocked kitchen, then step onto the wrap-around deck surrounded by cedar forest. After hiking the Bruce Trail, skiing at Beaver or Blue, paddling Lake Eugenia or enjoying a foodie-road-tour, sink into the sparkling hot tub. Evenings end around the wood stove or the outdoor fire-pit under a star-filled sky. Fast Wi-Fi, cozy beds and thoughtful touches make every stay easy, relaxing and memory-filled.

KitchenFamilyGrill

4.87 out of 5 average rating, 451 reviews

An aerial view of the tiny house surrounded by lush greenery and trees. The rustic wooden structure features a slanted red roof and an inviting porch area with seating. A clear view of the grassy land leads to the house, emphasizing its quaint and natural setting.

Tiny home in Meaford

Tiny Home Nestled between Thornbury & Meaford

Tinyhome situated 10 min to Thornbury and Meaford, and 20 min from Blue Mountain Village, nestled a country/residential area so it is quiet and dark at night. Has all the basic comforts including spacious 3 piece bathroom. Close drive to beaches and many hikes and cross country ski trails in the area. It is also a 15 minute drive from Beaver Valley Ski Club and a number of different cideries. Shared heated pool available for the summer months. Window Aircon/pool opens end of May or June.

FamilyKitchenSleep quality

4.98 out of 5 average rating, 427 reviews

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

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.

KitchenFamilyBathroom

4.97 out of 5 average rating, 137 reviews

Chalet in Meaford

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!

FamilyKitchenAccuracy

4.99 out of 5 average rating, 106 reviews

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

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 spacesKitchenCleanliness

4.93 out of 5 average rating, 860 reviews

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

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🌿

Indoor spacesKitchenHospitality

4.94 out of 5 average rating, 144 reviews

A charming A-frame cabin is surrounded by tall trees, featuring a triangular roof and wooden siding. The entrance includes a white door with a window above, complemented by a small wooden deck with stone accents.

Cabin in Clarksburg

Tiny A-Frame near the Bruce Trail

Find yourself nestled among pines trees just steps from the Bruce Trail! This 100 sq. ft. tiny A-Frame offers cozy comfort with two stackable twin beds that convert into a queen (side-by-side) when desired. Amenities include the essentials: BBQ, drinking and dish water, power box to charge devices and a small light, plus an outhouse with a composting toilet. Centrally located near Old Baldy Lookout, Beaver Valley, Blue Mountain and Duncan Caves. The perfect spot to relax and unwind!

Indoor spacesFamilyValue

4.95 out of 5 average rating, 159 reviews

Cottage in Flesherton

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.

FamilyKitchenAccuracy

Popular amenities for Grey Highlands family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.96 out of 5 average rating, 101 reviews

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

Beaver Valley Escape - HotTub & Outdoor Pizza Oven

FamilyKitchenHospitality

4.83 out of 5 average rating, 103 reviews

A modern kitchen features a large island with a sleek countertop and ample storage below. The space includes stainless steel appliances, a geometric tile backsplash, and warm wood accents. Natural light floods in, highlighting the open concept layout that connects to the dining area.

Cottage in Flesherton

Lake Eugenia-Private, Quiet Retreat

KitchenIndoor spacesLayout

Chalet in The Blue Mountains

A warm living area features leather sofas adorned with soft throws, along with a daybed lined with colorful cushions. A cozy wood stove is positioned nearby, providing a focal point. Natural light streams through the glass doors, complemented by rich purple curtains.

Stylish Log Chalet w/ Hot tub Minutes to Village

KitchenFamilyOutdoor spaces

4.91 out of 5 average rating, 112 reviews

4.98 out of 5 average rating, 116 reviews

An open game room features a polished wooden pool table at its center, surrounded by exposed timber beams and vibrant green walls. Large windows provide natural light, while a television is mounted nearby. Additional seating is available, enhancing the space's social atmosphere.

Home in Meaford

Birdsong, the perfect Blue Mountains getaway

KitchenFamilyDecor

4.97 out of 5 average rating, 114 reviews

Home in Meaford

Stonefox Retreat: Acerage, Pond, Hot Tub & Sauna

Indoor spacesKitchenSleep quality

A spacious open-concept living area is highlighted, featuring a large dining table set for meals. The kitchen is equipped with modern appliances and black cabinetry. Natural light enters through multiple windows, enhancing the inviting atmosphere of the space.

4.99 out of 5 average rating, 231 reviews

Lovely 3 Bedroom Condo with Stunning View and Pool

Indoor spacesFamilyCheck-in

4.85 out of 5 average rating, 384 reviews

An indoor hot tub is surrounded by wooden paneling and large windows that allow sunlight to fill the space. Natural stone accents and a serene greenery image on the wall enhance the calming atmosphere. Two wooden chairs are positioned nearby for relaxation.

Cottage in Kimberley

A Cozy Country Retreat *Indoor Hot Tub* Ski* Wi-Fi

FamilyKitchenParks

The living area is designed with a cozy sectional and an armchair, accompanied by a coffee table. A television is mounted above a stone fireplace. Large windows provide ample natural light and views of the surrounding hills and golf course.

4.95 out of 5 average rating, 1021 reviews

Maple & Mountain | Pool/Hot Tub/Shuttle/WalkToBlue

KitchenFamilyHot tub

Family- and pet-friendly home rentals

4.96 out of 5 average rating, 128 reviews

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

MapleHaven Cabin @ Lake Eugenia

KitchenFamilyPets

4.99 out of 5 average rating, 154 reviews

A log cabin exterior showcases a blend of rustic charm and natural surroundings. The structure features various window styles, allowing light to enter, while green grass and garden elements enhance the peaceful ambiance. Surrounding trees create a serene and private setting.

Cabin in Holstein

Kettle Creek Cabin

Indoor spacesKitchenParking

4.96 out of 5 average rating, 177 reviews

A peaceful beach scene captures the soft sand shoreline leading to the water's edge. Gentle waves lap at the shore, and the sky is filled with warm sunset hues. A cottage is visible in the background, nestled among trees, enhancing the serene atmosphere.

Cottage in Tiny

Ultimate Georgian Bay Vacation Getaway

Indoor spacesFamilyOutdoor spaces

Cottage in Grey Highlands

A wooden deck connects two buildings, featuring outdoor furniture including two lounge chairs and a blue plastic chair. A picnic table is positioned in front, and a grill can be seen nearby. Lush greenery surrounds the area, providing a calm outdoor environment.

Private 5 Acre Chalet with Bunkie & Sauna

Indoor spacesKitchenCleanliness

4.95 out of 5 average rating, 163 reviews

4.97 out of 5 average rating, 174 reviews

A charming century home features a blend of red brick and light siding. The entryway is highlighted by a covered porch and decorative star. Lush greenery surrounds the property, adding to its inviting appeal under clear blue skies.

Home in Meaford

Beach & Hiking Nearby • Large Private Fenced Yard

FamilyKitchenAccess

Home in Blue Mountain Resort Area

The living area features a modern design with a stone fireplace and a mounted TV. Large windows allow natural light, while a spacious coffee table sits between a sectional couch and a sleek armchair. A neutral color palette is complemented by decorative plants.

Mountain Cedar Chalet! Across from The Village

KitchenFamilyCheck-in

4.97 out of 5 average rating, 432 reviews

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.

Beautiful Riverside Country Apartment

KitchenFamilyGrill

4.96 out of 5 average rating, 345 reviews

Townhouse in Blue Mountain Resort Area

A clear, inviting outdoor pool is surrounded by landscaped greenery and stone seating areas. The pool features a curved shape with steps leading in, and two poolside lounge chairs are visible. Mature trees provide shade in the background, enhancing the serene environment.

Walk 2 Village, Great Kitchen & Beds, Summer Pool!

KitchenFamilyParks

4.96 out of 5 average rating, 372 reviews

Family-friendly home rentals with a pool

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.

4.93 out of 5 average rating, 312 reviews

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

Indoor spacesKitchenCheck-in

4.98 out of 5 average rating, 252 reviews

The entrance showcases intricate woodwork and architectural details, with a grand staircase leading to the upper level. A large door opens to the outside, and a vintage chandelier illuminates the inviting foyer, highlighting the craftsmanship of the historic home.

Home in Owen Sound

Butchart Estate: Breathtaking Victorian mansion

FamilyIndoor spacesPool

Apartment in Blue Mountain Resort Area

An open layout of the studio unit is displayed, featuring a modern kitchen with a breakfast bar and sleek cabinetry. The cozy living area contains a pullout sofa with decorative cushions, and a spacious king bed is situated in the corner, complemented by subtle green accent walls.

Evergreen Studio | King Bed/Pool/Hot Tub/Shuttle

Indoor spacesKitchenLayout

4.96 out of 5 average rating, 258 reviews

The living area features large windows providing natural light and views of the outdoors. A comfortable sofa and armchair are arranged around a round coffee table, while a gas fireplace adds warmth. A TV is positioned for easy viewing, creating a welcoming space for relaxation.

4.94 out of 5 average rating, 177 reviews

Three Suns | Pool, Hot Tub & Shuttle

FamilyKitchenBackyard

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.

4.92 out of 5 average rating, 201 reviews

Blue Mountain condo in Historic Snowbridge

KitchenFamilyParking

A bright kitchen and dining area feature a modern white countertop with seating, complemented by a wooden table surrounded by dining chairs. Natural light enters through several windows, and a clock adorns the wall, enhancing the space's functionality and warmth.

4.95 out of 5 average rating, 184 reviews

Rustic Chic Renovated 2Bd Condo by Village

KitchenIndoor spacesLong stay