Family-friendly holiday rentals in Grey Highlands

Jason had a beautiful home that we were grateful to spend our Christmas holidays at. When there was an issue with electronics that we needed help with, not only did he respond rapidly but also came in person to help rectify the issue. A beautiful home and a wonderful host. :)

This place was perfect for a blue mountain get away. We had 8 adults stay here for a ski trip and we all were comfortable and had a wonderful time. The kitchen is well stoked so we were able to make large communal meals with no issues. I'll definitely look into coming back next year.

Had a wonderful stay at this beautiful Muskoka cabin. Great views of the lake and was really fun to go out on the canoe and kayaks. The cabin was cozy and nice with a great kitchen and awsome living room for hanging out and relaxing. Host was extremely responsive and nice. She provided helpful clear instructions and information. Would love to go back.

Sara’s place was absolutely spectacular! Every little detail was thoughtfully considered, making it perfect for a big group or family. From an abundance of towels, blankets, and dishes to a well-stocked kitchen with spices—you name it, they had it! Our family frequently rents large homes, and it's usually hard to please everyone, but this time, not a single person had any complaints—only praise for how much they enjoyed the stay. The amenities were top-notch! We made great use of the sauna, red light bathrooms, and hot tub. Plus, the home offered plenty of gathering spaces for both adults and kids to relax and enjoy. It was truly a comfortable and welcoming experience. We would absolutely stay here again and highly recommend it to anyone looking for a well-equipped, thoughtfully designed getaway!

Our host was very respectful, responsive, and helpful throughout our stay. The cottage was well-equipped with everything we needed and offered great amenities. The location was also convenient and pleasant. Overall, we had a wonderful time here and would definitely recommend this place to others!

We had a wonderful time in Steve and Jane's quaint and cozy cottage! The beautiful view and the sound of the water made our time spent there enjoyable and peaceful. The cottage was clean, instructions were clear and they had everything you might need to make your stay a wonderful one. Steve and Jane were also quick to respond to any questions we had prior to and during our stay. Amazing hosts!! Thank you for a great time!

Amazing cottage and host. All amenities are/were in perfect condition and the property looks just as it does in the photographs, if not better. There are flat lawns in the front and back for a game such as croquet. It is also about fifteen minutes away from Georgian Bay. I have bookmarked this cottage for future visits! 10/10!

my group had such a good time at this cabin. it’s a beautiful area super close to the blue mountain village. we felt right at home and taken care of. the host is quick to respond to any questions we had and would message to check in with us every so often.

Another prefect stay at DJs place. We will definitely be booking again next time we are in the area.

I can’t say enough good things about the lodge! First of all, Esther is an amazing host and the space is so conducive to group trips. We went for a bachelorette with a “retreat” theme. Esther offers classes and we did the breathwork class, it was so calm and peaceful — the birds were singing while we did the class in the loft and Esther was a very effective facilitator! All the girls loved doing the sauna in the morning and we had a campfire in the evening. In terms of things to do near the lodge, it was also only a 20 min drive to Georgian hills winery, and 30 min from the water where we took Collingwood charters for a live music boat cruise. Tons of sleeping space at the lodge, was initially nervous that single beds wouldn’t be comfy but we all slept very well and the bedding was lovely. Lots of washrooms/showers which again was amazing for a large group of ladies, especially when we were all getting ready together for the day! Decor and overall vibe of the lodge is unique & cute!!

This was our second year at Carrie and Dan's cottage and once again my family and I had a fantastic time. The house is perfectly situated on the river with a nice beach and it has all of the amenities needed. Dan communicated regularly and checked in with us to ensure we had everything we needed. This is a beautiful property which anyone would have fun at.

Condo was beautiful, relaxing and everything was walkable. Will definitely be back!

Our stay here was fantastic. The house is big with plenty of rooms for a big group. It was clean and orderly. There is a beautiful dock with a canoe, kayak and life jackets. Our host Fred was very kind and accommodating. I would recommend this to anyone looking a cottage getaway.

My boyfriend and I rented Steve’s cabin for a birthday weekend and loved our stay. It was both recharging and relaxing. Being surrounded by nature all weekend felt grounding and the quiet was just what we were looking for. The bed was so comfortable and the whole cabin was so clean. Communication with Steve was great and he was so nice to chat with when we arrived. Although his home is just next door you’d never know he was even on the property unless you needed him. We did quite a bit of fishing during our stay and caught a pike on the first night! Thanks for a great stay!

Great little cottage. Its a beautiful spot. My only critique would be we could have used an umbrella for sitting outside, howver it was a heat wave and may not have helped! And only comment maybe is bring your own dishclothes and tea towels. I know it says towels and bedding but i wasnt thinking specifically these items. Well worth the $$.

We absolutely loved our 4 night stay! The space was spotless, and steps away from the ski hill as well as the village. Everything was as described, lots of room which was ideal with a toddler. The kitchen was stacked with all of the essentials and more for cooking which isn’t always the case. Lovely energy from the hosts as well. Would absolutely return! Thank you Amir and Ulana for the perfect accommodation :)

Susan’s place was clean, well-equipped and pristine. It was indeed a beautiful retreat, complete with hot tub and a pool. Communication with her was always pleasant and accommodating. Everything was well thought-out.

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!

Would recommend this property for its space and proximity to the village! Jonathan is attentive and very responsive. Our family enjoyed our stay

10 STAR!!! Amazing property! Impeccably maintained gorgeous cabin (rustic/modern and very classy) and surrounding grounds. So lovely! The hosts have thought of absolutely everything. I didn't want to leave! Now on my bucket list to return, hike Mono Cliffs then relax by the sparling clean pool. The Trails Retreat Cabin is an affordable deluxe property that you really should treat yourself to!

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!

We stayed here over the long weekend and absolutely loved it! The place was gorgeous—cozy, clean, and the view of the mountains from the Airbnb was stunning. The beach just two minutes down the road was also beautiful and made the stay even better. We’ll definitely be booking this place again whenever we return to Blue Mountain!

Jason and Tanya saved our trip after the first Airbnb we checked into was dirty and had mice! They had a last minute cancellation and allowed us to check in right away! They were super helpful in getting us moved over to their place. When we got inside it was beyond clean and comfortable. The kitchen was the best of any airbnb I've stayed in with spotless dishes and useable pots/pans and appliances. The unit is spacious and the beds & linens were extremely comfortable. A million thanks for saving our trip for us! Would highly recommend to anyone.

Richard was an extremely gracious and helpful host who responded immediately upon my reservation request. He answered every question I had in a very timely manner and helped me to get in contact with Airbnb when I had a separate issue that had nothing to do with his booking. When we arrived at the bnb, there was a complimentary bottle of white wine waiting in the fridge for us. Shortly after we checked out, he reached out to let me know that I had left one of my belongings in the closet and offered to return it to me. He also gave me a discount for our stay due to an unforeseen circumstance that was beyond his control. He was very generous and helpful and went above and beyond to accommodate us! Our stay was quiet, clean, comfortable and cozy! We will stay there again when we visit Collingwood and highly recommend it!