Family-friendly vacation rentals in Grey Highlands

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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

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

4.93 out of 5 average rating, 152 reviews

Whispering Pines Cabin in Woodland Acres

Experience this nature retreat just 60 km from Toronto and feel like you’re thousands of miles away. The perfect glamping experience for any nature lover looking for a relaxing getaway. There is power in the bunkie which offers the convenience of lighting, cell phone charging, an electric fireplace, a kuerig coffee maker and mini fridge with freezer. Pursue your favourite outdoor activities during the day and then return to your cozy queen size bed and sofa bed just steps away from the bonfire.

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, 166 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

Top guest favorite

An inviting outdoor space features a cozy fire pit surrounded by gravel and wooden seating. Soft lighting from above highlights the stone wall and enhances the serene atmosphere. The area provides a perfect spot for relaxation and outdoor gatherings.

Barn in Eugenia

4.98 out of 5 average rating, 193 reviews

Blue Barn Bed n Bale / Blue Mountain

2 q beds. Main bunky bed, 1 bedroom (please inform if second bed is needed) A relaxing, peaceful farm stay on a working farm with or without your horses. Bright clean bunky built in 2016 in our 160 year old barn. The space is new, cozy and offers a chance to spend hours of time with your horses or ours. Nothing like having coffee with the horses.We back on to 30,000 acres of trailed crown land and the Kolapore Trails lending itself to horseback riding, hiking, snow shoeing, mountain biking.

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, 127 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.

Top guest favorite

The entrance of a yurt is featured, showcasing a wooden deck with a decorative orange door. The circular structure is surrounded by lush greenery, highlighting the natural setting. Soft light filters through the trees, creating a peaceful outdoor environment.

Yurt in Meaford

4.99 out of 5 average rating, 153 reviews

Quiet Retreat for Two

Spend a starry night in the country with the comfort of a soft bed, a wood stove, and plenty of space both indoors and out. Our yurt is located in a pocket of trees next to rolling farm fields and beautiful conservation land that the Rocklyn creek meanders through. You can prepare your meals in a sweet outdoor kitchen that is entirely screened in- or choose to sit by the fire. Bruce Trail access is just around the corner, and the towns of Meaford and Owen Sound are a short scenic drive away.

Guest favorite

A modern living area features a cozy brown leather sofa complemented by black accent pillows. A large flat-screen TV is mounted above a fireplace, and a wooden coffee table displays a decorative tray. Natural light streams through sliding glass doors leading to a patio area.

Condo in Blue Mountain Resort Area

4.88 out of 5 average rating, 251 reviews

Northern Peaks - Outdoor Pool / Shuttle to Blue

Northern Peaks is an updated loft located in North Creek Resort at the North Base of Blue Mountain. Ideal location for those seeking easy access to the ski hills and hiking trails but still within minutes to Blue Mountain Village. North Creek resort offers a free shuttle service to Blue Mountain Village, an outdoor swimming pool open in the summer months, two hot tubs year round, tennis courts with night lights, charcoal grills and community picnic tables that you can use during your stay.

Guest favorite

The exterior of the chalet features a two-story structure with large windows providing ample natural light. A small balcony is visible above the lower level, accompanied by a natural gas BBQ. Colorful adirondack chairs in red and blue are placed on the patio, surrounded by green shrubbery.

Chalet in Blue Mountain Resort Area

4.91 out of 5 average rating, 402 reviews

Modern Ski In/Out Mountain Side Ground Floor

SKI IN AND SKI OUT from the back deck (snow dependent)!! Notice the amount of comfortable seating for NINE PEOPLE around the TV that many other places are without. At the end of a long ski day having a comfortable place for everyone to sit is what most Chalets are missing. Enjoy our family’s beautiful renovated GROUND FLOOR chalet with 2 Bedrooms, 2 Baths, 6 Beds conveniently located next to the Blue Mountain Inn. Blue Mountain Village is a 7 minute walk away. Location, Location, Location

Superhost

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

4.85 out of 5 average rating, 378 reviews

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.

Top guest favorite

A serene outdoor space features four wooden chairs arranged around a fire pit on lush green grass. Behind, two vibrant autumn trees stand beside a tranquil lake, framed by a white fence and scenic hills in the background.

Guest suite in Kimberley

4.96 out of 5 average rating, 243 reviews

"Wine Down" in Scenic Grey Highlands

Join us at “Wine Down”, our beautiful property located on the highlands of the Beaver River Valley, just minutes away from all that Georgian Bay and the Blue Mountains have to offer. It is a very private 1 acre property with an incredible view of water, escarpment and wildlife. Enjoy more than 1,000 sq. ft. of living space including beds for 5, fully equipped kitchen, dining area, living room with large screen TV and full bathroom. Your hosts live on sight in the main level of the house.

Guest favorite

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

4.97 out of 5 average rating, 115 reviews

Tiny A-Frame near the Bruce Trail

Find yourself nestled among white pine trees just steps off the Bruce Trail! This tiny A-Frame is 100 sq.ft providing enough room for cozy comfort. The cabin is equipped with 2 stackable twin beds converting into a queen bed when desired. Our amenities contain all the essentials, including a BBQ, drinking and dish water, and an outhouse with a composting toilet. Centrally located to Old Baldy Lookout, Beaver Valley, Blue Mountain and Duncan Caves. The perfect spot to relax and unwind!

Guest favorite

A serene backyard features a glowing hot tub and a cozy fire pit surrounded by colorful chairs. Soft string lights create a warm ambiance against the night sky, highlighting the green lawn and wooden fencing that offers privacy.

Guest suite in Kimberley

4.94 out of 5 average rating, 738 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🌿

Guest favorite

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.

Chalet in Grey Highlands

4.95 out of 5 average rating, 143 reviews

Private 5 Acre Chalet with Bunkie & Sauna

An enchanting, private, 4 season retreat in the escarpment atop Beaver Valley, metres from a beautiful section of the Bruce Trail. The property has nearly 5 acres with cut trails, hammocks, and a sports field. It has two buildings connected by a large deck that has outdoor furniture and a BBQ. The sauna is just feet away. The buildings are fully outfitted offering a comfortable base for daily adventuring, or a stay put retreat. This spot is ideal for a family, or a couple's getaway.