Family-friendly holiday 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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Guest favourite
A spacious living area features a comfortable brown sofa positioned near a glass coffee table. Natural light pours in through large windows with blinds, illuminating a dining area with seating for four. A modern kitchen is visible in the background, equipped with sleek appliances.
Guest suite in Moonstone
4.86 out of 5 average rating, 284 reviews

RELAX @ our HOT TUB and SAUNA in the woods

PLEASE READ! Mt. St. Louis & Horseshoe Valley at doorstep! This is a bright, large and private walk-out GUEST SUITE (basement apartment). Hot tub, patio, fire pit & secluded path in the woods to enjoy nature. Kitchen is equipped with an induction cooktop and all things necessary, even wine bottle opener:) Open concept living room/kitchen/dining room with TV & Roku. Bedroom is a work of Art: dark, mysterious and romantic! Custom Queen bed made from weathered barn wood salvaged from our property.

Guest favourite
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
4.96 out of 5 average rating, 414 reviews

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...

Top guest favourite
A rustic bunkie is nestled among lush trees, featuring a wooden porch with steps leading to the entrance. Two outdoor chairs are positioned beside a circular stone fire pit, creating a relaxed atmosphere for gatherings. A variety of greenery surrounds the area.
Guest house in Neustadt
4.93 out of 5 average rating, 410 reviews

Bunkie in the Country

Last day of season Nov.28th The bunkie has a great view of the sunrise. It's a quiet rural area (please note it is a GRAVEL road). Good for couples, solo adventurers, hunters, someone looking to be outside of town. The bunkie is located approx. 30 feet behind our home. We have 1 large dog on site (lives in the house). For allergenic reasons and safety of other animals, we do not allow pets. May not be suitable for those with mobility issues (small hill & stairs). The bunkie has heat and A/C!

Top guest favourite
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, 167 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

Guest favourite
A cozy sleeping area is highlighted by a black wooden bed frame with a crisp white bedding set. Decorative pillows are arranged on the bed, while a framed image of a bear adorns the wall. Soft bedside lighting is provided by sconces, complementing the mirror opposite.
Flat in Blue Mountain Resort Area
4.9 out of 5 average rating, 164 reviews

Blue Mountain Studio Retreat

Our cozy studio is located at the base of Blue Mountain at the North chair lift, with ski in / ski out access. Perfect for 2 or a couple with small children, this newly renovated Studio has 1 bedroom, 1 bathroom and sofa bed; fully stocked kitchen, electric fireplace and flat screen T.V. Only 1 km from the Village with many restaurants, shopping and activities. Enjoy a short trip to the Scandinavia Spa or many close by beaches. Blue Mountain is a great place for the whole family to enjoy.

Guest favourite
An industrial-style apartment features a spacious open living area with a dark leather couch and a wooden coffee table. A staircase leads to an upper sleeping area, while concrete walls provide a modern backdrop. Natural light enters from nearby windows, enhancing the interior space.
Farm stay in Township Of Southgate
4.85 out of 5 average rating, 179 reviews

Loft Where City Meets Country With Hot Tub

This unique place has a style all its own, while situated on a very private 39 acres where city style meets country living. The industrial apartment has been designed inside of a driving shed and offers all the luxuries of real glamping. Comfort and style throughout, complete with hotel quality mattress and linnens. The forested trails and beautiful property are a nature lovers paradise. You will find everything needed for a perfect getaway rather walking the trails or relaxing by the pond!

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, 394 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 favourite
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, 250 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 favourite
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, 761 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🌿

Top guest favourite
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, 150 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.

Top guest favourite
An outdoor space features a picnic table with an umbrella, set near a tranquil pond. A stack of firewood is positioned beside a large tree, with a fire pit nearby. Lush greenery surrounds the area, creating a peaceful atmosphere.
Guest house in Southgate
4.93 out of 5 average rating, 216 reviews

Cozy, quiet, clean cabin with wi-fi and fire pit.

Welcome to Penny Creek. A simple cabin just south of Durham. A private location surrounded by ponds, streams and forest - yet close to many day adventures should you want to explore beyond the property. Nearby amenities include restaurants, grocery, lcbo, fuel, coffee and shopping . An open concept space that offers one queen bed and a pull out sofa. Full kitchen and bath. Picnic tables, Fire pit and bbq. Excellent hiking trails nearby. Easy access to ofsc (snowmobile) trails!

Top guest favourite
A spacious building is seen with a large deck overlooking a tranquil pond. A canoe rests on the grassy bank, with a stone waterfall nearby. Bright seating areas are arranged on the porch, surrounded by lush greenery and well-maintained landscaping.
Farm stay in Fergus
4.96 out of 5 average rating, 294 reviews

Waterpark Acres

Waterpark Acres offers a unique country experience to relax with spectacular views from the balcony. You have complete privacy in this separate building. No other rooms are rented out while you are here. See farm animals ( horses, llama's, dogs, sheep, pheasants and other birds. Also some out of the ordinary animals including kangaroos, lemurs, kinkajou's, parrots etc. ) Please note : WEDDING EVENTS are not hosted on this property

Popular amenities for Grey Highlands family-friendly rentals

When is the best time to visit Grey Highlands?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$257 SGD$277 SGD$237 SGD$205 SGD$229 SGD$241 SGD$277 SGD$305 SGD$215 SGD$224 SGD$198 SGD$293 SGD
Avg. temp-7°C-6°C-1°C6°C12°C17°C20°C19°C15°C9°C3°C-3°C

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

  • Total holiday rentals

    Explore 970 holiday rentals in Grey Highlands

  • Nightly prices starting at

    Grey Highlands holiday rentals start at $52 SGD per night before taxes and fees

  • Verified guest reviews

    Over 56,110 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 420 rentals that welcome pets

  • Holiday rentals with a pool

    350 properties feature pools

  • Rentals with dedicated workspaces

    580 properties have a dedicated workspace

  • Wifi availability

    950 of Grey Highlands holiday rentals include wifi 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!

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