
Family-friendly vacation rentals in Grey Highlands
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Top-rated family-friendly rentals in Grey Highlands
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Popular amenities for Grey Highlands family-friendly rentals
Family-friendly home rentals with a hot tub

A Cozy Country Retreat *Indoor Hot Tub* Ski* Wi-Fi
Thank you for the wonderful stay! Our group loved our stay! Would highly recommend.

Trenanthia "Cahoots" Cottage: HotTub,Sauna,GamesRm
Christine & Rebecca were very kind and always provided quick and useful answers to all our questions. 5 stars landlord The house is super big, organized and has so many amenities to entertain yourself, no matter how is the weather outside. Would definitely consider to return in a near future for a gateway with my friends.

Chalet At Blue - Private chalet with hot tub
Great communication with Shawn from start to finish, the home was what we expected and equipped with almost everything we needed. Lots of parking available, great spaces for groups to hang out, easy to host team meals. We were there for a ski trip and got pounded with snow, burying all sidewalks and making the walk to villages and chairlifts more difficult - but doable.

Lake Simcoe-3bdr,hot tub,sauna,swim,play,hike
Nice home in a quiet and safe feeling neighbourhood. Easy to find and access. Big back yard for kids and dog (although not fully fenced, which was fine as we brought our own leash). We arrived from out of province (via flying) and were surprised to find the beds already made with the necessary linens (we had packed our own via suitcase as per the ad details). But we appreciated the kind gesture had we somehow failed to bring our own! The kitchen is updated (so different from pictures) but still has all the appliances and cooking items a family would need for their stay. Lots of stores (grocery, banks, restaurants, Canadian Tire etc) are within a 10 min drive or less, making “going into town” to grab stuff a breeze. Plus having access to a hot tub, sauna and BBQ are a very nice treat :) We had a very comfortable stay and appreciated Tamila’s prompt responses for any questions we had. Would happily stay again!

Heart of Kimberley - with views and a hot tub
Thanks for a great stay!

Century Home in downtown Owen Sound - Hot Tub
Excellent place to stay. Very clean. Very accommodating.

Rustic Spanish Chalet inthe Heart of Nature/hottub
We booked this home for a family and friends cottage weekend and the place was exactly as described. It is a beautiful home very close to the slopes with lots of things to do (billiards, board games, hot tub, TV, BBQ). The host was very kind and responsive and was very flexible with out checkout time, which was very nice. Our group of 11 people all had a great weekend and we would definitely book this place again :)

ReLive Hilltop Chalet w/brand-new hottub, sunrises
We had a great stay in this cabin on a GORGEOUS wooded property. Awesome to watch the snow fall against the old pines. I took my dog on the snowshoe trails. Very cozy and it was great to get out of the city.
Family- and pet-friendly home rentals

Luxury, Waterfront, 4 bdrm Bungalow in Sth Muskoka
Even with a series of unfortunate weather events the stay was great! Do and family are responsive and kind and the place was fantastic! We will be back!

Country Cabin Escape | King Bed | Pet Friendly
one of my all time favorite places I've stayed. there was nothing even remotely sub par about the location or accomodations. beautiful and quiet. great communication and easy check-in and out. 10/10 fabulous

The SEED lodge: A Rural Retreat & Gathering Place
Awesome place for our friend group to get together (families with kids ages 3-11) Tons of cooking spices, bowls, plates, mugs. Sauna is a nice touch and so is the fire pit. Large property for the kids to run around. I wasn't sure about the single beds but they were very comfortable. Nice bathroom/shower set up. Perfect for a large group. Would go back!

Entire House w/ Games Room- by Beaches & Downtown
Great place, will stay again

Luxury 5 beds, 6 Baths custom home
Jay’s place was great for our family. Big space, lots of rooms, nice big kitchen. Bring more towels if you’re a big group. One of the showers was leaking to the floor below (Jay was really responsive to get this fixed, which he said he’d do after our visit). Kitchen is huge and definite plus if you’re with a big group, was a nice place to gather each morning and make breakfast together! Well stocked, though missing a basic frying pan. If you have elderly family, the stairs are a bit difficult to navigate. And lots of sharp edges around if you have little kids. Overall worked out well for our multi generation family trip!

SNAKE CABIN(rustic, 'off-the-grid')
Exactly as advertised - Beautiful property, cozy and comfortable off-grid cabin and super friendly hosts. Would absolutely come back and recommend to a friend!

All-Season Cottage on the Lake
Great place in a beautiful location! Perfect for our two families to get together and enjoy the outdoors in winter. The kitchen is well-supplied and it’s great to have towels and sheets provided. Carrie is friendly, flexible and well organized. Thanks so much!

Blue Barn Bed n Bale / Blue Mountain
We really enjoyed our stay in Kim’s spacious barn, with friendly horses and great views right outside the front door. We have loved exploring the area over the years and this is one of our more unique experiences.
Family-friendly home rentals with a pool

The Snowbridge Lookout on Monterra Golf Course
Beautiful condo, very clean, the most comfortable beds. Only downside is there is no bathtub We will return forsure

HotTub & Cozy Getaway - Headwaters Retreat
Had a great stay! The place was clean, comfortable, and exactly as described. The host was friendly and responsive. Would definitely recommend!

Luxury Vacation Home at Blue Mountain Village
This was a beautiful place with great views, only a 5 minute walk away from the village. It was clean with an organized bathroom and kitchen amenities. We weren’t missing anything. There was a nice fireplace with a lot of board games. Super cozy, and a great place to take photos. You also had access to a shared hot tub. Sometimes other people got rowdy at the hot tub, but that is to be expected. Overall this is a great place for families or get togethers for skiers and people that like great restaurants and social events. Thanks, Adam!

Your Peaceful Santuary in Nature
Would highly recommend! A very spacious spot with lots of activities and lovely surroundings. The place is very cozy with the wood burning stove and plethora of candles. Annette was very pleasant, responsive and accommodating! We had a great time playing with her dogs in the snow. We will be back!

Sunny Pines Farm Studio Tennis Court/Bruce Trail
What a gorgeous place to get away from the city for a few days. The comfortable studio has everything you'd need during your stay. The fields are great for walking (especially if you have a dog), and there are all kinds of magnificent hiking trails nearby. My arrival coincided with a massive ice storm and Vince and Miranda were in touch every step of the way, keeping me updated on conditions and options. They were a pleasure to deal with. I look forward to returning next time I need a taste of the country.

Stonehaven - large country retreat, with pool*
We struggled to find a place for our group of 17 and Stonehaven was an amazing find! The beds were comfortable, we loved being able to have meals all together in one spot, and there was lots of space for people to do different activities inside since it was winter. Outside, we enjoyed tobogganing, snowshoeing and cross country skiing on the property. Steve was quick to communicate and provided clear instructions and maps. We were already talking about going back so we can enjoy the property in the summer! Thank you for a memorable and fun weekend!

2 Bedroom, 2 Level Condo on Blue Mountain!
It was the best location in the village, and it was quiet and the sound of the stream was friendly. If you are skiing during the ski season, it would be very convenient because the bottom of the slope and the entrance to the building are in contact. The interior was clean and well-organized. Thanks, Richard.

Cozy Sleep 10 ,Hot Tub & BBQ, Steps to Blue Mtn
A lovely stay in Blue Mountain with my family for new years! Greg was extremely communicative and was always quick to respond with any inquiries. The location is walking distance to the village and the neighbourhood had the most friendliest people. We felt right at home and Greg's place had all the right amenities for our family's needs. We will definitely come back here for our next stay in Blue!
Quick stats about vacation rentals that are family-friendly in Grey Highlands
Total rentals
1K properties
Nightly prices starting at
ﺩ.ﺇ147 before taxes and fees
Total number of reviews
53K reviews
Pet-friendly rentals
450 properties allow pets
Rentals with a pool
340 properties have a pool
Rentals with dedicated workspaces
600 properties have a dedicated workspace
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- Blue Mountain Village
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- The Georgian Bay Club
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- Caledon Country Club
- The Georgian Peaks Club
- Inglis Falls
- The Club At Bond Head
- Shanty Bay Golf Club
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- The Pulpit Club
- Mad River Golf Club
- Springwater Golf Course