Apartment holiday rentals in Grey Highlands

This was my wife and I’s second time visiting Midland to attend the annual butter tart festival. Our previous rental unit last year was great as were the furnishing so the bar was high for this year’s Airbnb rental. In fact, the “Home in Midland” rental unit and the hosts exceeded our expectations. The rental unit's location was only minutes from the festival and most amenities such restaurants, waterfront and stores. We never moved the car during our stay since everything was within a short walk. About the hosts welcoming attitude and hospitality: Upon arrival, we requested an early entry which was granted without hesitation. We were also fortunate enough to meet one of the hosts (Shelby) she was extremely pleasant and assisted us in making sure we were in the right parking spot, which was well indicated. We walked up 2 flights of stairs to get to our unit and were pleasantly surprised at the space of the rental . The pictures online were absolutely on point and matched expectations.

Just what I was looking for. A peaceful stay close to nature. The train tracks right beside us was powerful. Caused me to stop and take it in. My wife said it was a reminder to stay present in the moment when a train passed. A lot of fun!

We enjoyed our stay very much. Great location, quiet and equipped with everything we needed. Jo took very good care of us. Will be back.

⭐️⭐️⭐️⭐️⭐️ One of the Best Airbnb Stays Ever! This was truly one of the best experiences I've ever had with Airbnb. From the moment we walked in, everything felt special — the apartment was beautifully designed, warm, and welcoming, with softly lit scented candles already creating a cozy atmosphere. We were also greeted with thoughtful touches like a complimentary bottle of wine, cookies, and yogurts for breakfast — such a kind and generous gesture! The place itself is quiet and peaceful, and enjoying morning coffee by the little lake with the fish was simply magical. This stay made our weekend unforgettable. Huge thanks to Adele, our wonderful host — your hospitality and attention to detail were incredible. I wish you continued success with your business, and I’d return in a heartbeat. Hands down, the best Airbnb experience I’ve ever had! 💫

Great apartment! Very modern and clean. The bed was extremely comfortable! Loved the bathroom with the double sinks. Everything I expected it to be and more!

This was one of the most beautiful places I've ever stayed! I attended a wedding in the area and my only wish is that I had more time on the property. I would recommend this place to anyone and I hope I can stay again.

Ana was an amazing host. She was very responsive and helpful. My friends and I loved the location and space. It is even better in person. The unit is private with a beautiful view of the grounds and ponds. We enjoyed walking the property and being close to town for dinner. Ana also left us some delicious Portuguese tarts, which was a lovely, unexpected touch. We highly recommend her place and are already planning our next visit. Thank you, Ana, for a fantastic stay!

This was our second stay. The Snug is a lovely place. The hosts are very accommodating. Perfect, comfortable location in downtown Orangeville. Very clean and has all the amenities you could need. The shower is fabulous. We've already booked our next stay! 😊😍

Hands down the best Airbnb we’ve ever stayed in After almost three years of Airbnbs around the world, this one in Canada tops them all. We stayed in both the Lookout (the little house) and the Pine Lodge (above the store)—and didn’t want to leave. The Lookout felt like a cozy sanctuary: garden, sauna, spotless, fully equipped. The Pine Lodge had a steam room (huge bonus!), comfy couches, a big dining table, and a fire always going. But what made it truly special were Krystal and Madison—the kindest, most caring hosts we’ve ever had. It felt like arriving at friends’, not strangers’. During a freak ice storm, they moved us to a backup-powered house and even brought us food. Just wow. Local tips: • Cawaja Store: best coffee, insane ice cream, and local broths, pies, soups. • Mums Restaurant: old-school diner, fresh, cooked-to-order food. • The Friendly Corner: lovely for sunny outdoor meals.

It’s a great unit, clean, has everything you need and walkable to downtown. Thank you!

Catherine’s place was just as expected; beautiful decor, clean, and spacious. It’s walking distance to the trail and dog park. Catherine was friendly and quickly responded to my inquiries. She also accommodated a late check out, which allowed my husband to continue working from home on the day of our check out. We highly recommend Catherine’s place!

Jessica’s place was incredibly spacious and featured a beautiful balcony overlooking the lake. The beds were very comfortable, and the home was well-equipped with everything we needed—including a patio barbecue. We stayed during a heat wave, and the air conditioning kept the space perfectly cool. The hosts were attentive and responsive throughout our stay. Overall, excellent value for the money—I would highly recommend this place and look forward to coming back!

Lissette was very considerate of our time and cared about our say. The unit was very clean, well decorated and nice personal touches to make it feel like a home which made our stay very comfortable.

love the location, very cozy felt at home. lots of amenities. Love the rain showers. washer and dryer a plus

We had a great stay! The place was spotless, the check-in process was super easy, and the location was perfect—just a short walk to the harbour. The host was very responsive and made sure everything went smoothly. We would definitely stay here again!

We stayed for two nights at Tarik's place, very close to downtown and we were able to walk to just about everything we needed. The place is super clean and also much larger than it appears in photos - there were 4 adults staying and we did not feel cramped at all. Tarik is quick to respond and reached out quickly when our power went out during an ice storm. We would definitely stay again.

Nice property, great location, Huong is a very responsive

We celebrated my daughter’s birthday at Ilyia’s place. She was very responsive and really tried to accommodate all our requests. The basement is spacious and the kitchen is lovely. I also really appreciate the painting that she made for our daughter. Thank you Ilyia! Few things I would comment is that the hot tub isn’t very clean. Lotss of dirt and leaves floating which we cleaned before use but we also found a bunch of hair at the bottom of the tub. The backyard chairs and table also need some cleaning. The bedsheets and blankets smelled musty/old which I don’t mind but my kids tend to smell everything and a bit bothered. However overall, we had a fun birthday weekend and I still give it a 5 star. Perfect for small event/gathering. Thanks again Ilyia and Larissa!

We absolutely loved our stay at Chantal and Sylvain’s place! From the moment we walked in, we were very impressed by this clean, cozy, and beautifully-furnished home-away-from-home. Our hosts thought of everything, and were friendly, responsive and helpful. Their place is complete with everything you could need for a comfortable stay, in addition to some additional thoughtful, special touches. We had fun playing some of the many available board games, and found it so peaceful to sit in their quiet backyard, surrounded by trees. We LOVED lounging in the beautiful hot tub. Next time we’re in Coldwater, we would definitely stay at Chantal and Sylvain’s place again! Highly recommend!

Sean is very Friendly and Professional. He responds to messages quickly. He is an amazing host where he is checking in on us ensuring if we needed anything he is only a phone call away. We have been going to the Resort for years. Easy to get too, very peaceful and the Units are so simple but nice. Not many places take pets but Sean's does which helped us alot. The beds are super comfortable, probably the best sleep I have had in a long time. Kitchen was equipped with everything we needed for our Stay. The Kids loved the gym to work out and then we spend quite a few hours at the pool. The fire pit was nice to sit at especially with the chilly weekend we just had. We will be back for sure to be Sean's Guest.

We had a great stay! very peaceful environment..

Sandra’s place is just like the pictures super cute, clean and private. The place has everything you need for a great stay. She’s very responsive to messages. It was our 2nd time enjoying her place and we’d look forward to booking with her again!

This was our second time staying at Julie’s place and it was great! Will definitely be going back.

Beautiful place definitely will be returning in the summer friday harbour is a must visit !!