
Family-friendly vacation rentals in Grey Highlands
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Top-rated family-friendly rentals in Grey Highlands
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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...

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

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.

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.

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.

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.

"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.

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!

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🌿

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.

Shipping container getaway in small country town
Walnut Grove is a 20-foot shipping container that has been lovingly assembled to showcase the restful, unhurried country life of small town Berkeley. Located two hours north of Toronto, this tiny home has plenty of natural light and all the amenities for a modern glamping experience. An ideal space for couples to unwind and explore the local lakes, rivers, waterfalls, and hiking trails (feel free to borrow our complimentary canoe!). Wi-Fi, fire pit, and free parking are available.

Natural Mongolian Yurt on Biodynamic Farm and Spa
The yurt is located on our 200 acre biodynamic farm in beautiful West Grey. Guest are welcome to walk around the property and enjoy being in nature. A cozy insulated space available all year round. This accommodation is rustic with outhouse (composting toilets), an outdoor shower and wash basin. Farm experience is also available. Snowshoeing or skiing trails are nearby or on the farm. The Spa (hot tub and sauna) is only available for private bookings for an additional fee.
Popular amenities for Grey Highlands family-friendly rentals
Family-friendly home rentals with a hot tub

Blue Mountain Getaway at North Creek Resort

*Blue Mountain Village* Pool, Hot Tub, WalkToBlue

Blue Mountain Condo. The perfect staycation!

Boho Beaver Cabin 1 with saltwater hot tub

Glamping Dome Riverview Utopia

Cozy Studio Mountainside stay in Blue Mountains

JJ’s small town country retreat

Sunset Cottage on Lake Eugenia -Hot Tub-4 Seasons
Family- and pet-friendly home rentals

Whispering Pines Cabin in Woodland Acres

Beautiful Riverside Country Apartment

Pine River Bunkies: Owl’s Roost Off Grid Cabin

The Scarlet Yurt Cabin, stay cozy w/warm fireplace

1BR Boutique Suite #6 - The Lake at Blue Mountains

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

Base of the Mountain, 2 Bedroom Loft Condo.

Tiny Home for 2. Hot Tub, Outdoor Shower, Outhouse
Family-friendly home rentals with a pool

Woodski Retreat w/Heated Pool on 3+ Private Acres

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

3BR Sierra Scandi Chic - Closest to Village

Evergreen Studio-KingBed/Pool/HotTub/Shuttle

Sunshine Summit - Outdoor Pool / Shuttle to Blue

Hidden Haven - Shuttle to Blue / Private Patio

Highlands Lodge & Loft - Shuttle to the Village

Cozy & Charming Retreat at Blue Mountain
Quick stats about vacation rentals that are family-friendly in Grey Highlands
Total rentals
970 properties
Nightly prices starting at
$56 CAD before taxes and fees
Total number of reviews
56K reviews
Pet-friendly rentals
420 properties allow pets
Rentals with a pool
350 properties have a pool
Rentals with dedicated workspaces
580 properties have a dedicated workspace
Destinations to explore
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- Blue Mountain Village
- Cobble Beach Golf Resort Community
- Horseshoe Resort
- Snow Valley Ski Resort
- Beaver Valley Ski Club
- Osler Bluff Ski Club
- Craigleith Ski Club
- Devil's Glen Country Club
- Hockley Valley Resort - Golf, Spa and Ski
- The Georgian Peaks Club
- TPC Toronto at Osprey Valley
- Mount St. Louis Moonstone
- The Club At Bond Head
- Caledon Country Club
- Barrie Country Club
- The Georgian Bay Club
- Alpine Ski Club
- Toronto Ski Club
- Mansfield Ski Club
- Legacy Ridge Golf Club
- Heritage Hills Golf Club
- Inglis Falls
- National Pines Golf Club
- Horseshoe Adventure Park