Cottage vacation rentals in Grey Highlands

Our stay was absolutely perfect! The house was beautiful, exactly what we had hoped for, and even better in person. It was clean, comfortable, and had everything we needed for a relaxing getaway. David was incredibly responsive and made the entire process smooth and enjoyable. We couldn’t have asked for a better experience and will definitely be making this an annual trip. Highly recommend!

We had an amazing winter stay at this cabin! While the driveway was a bit tricky due to the winter conditions, the host was extremely responsive and gave us helpful instructions to navigate it. The cabin itself was cozy and well-equipped, making it a great place to unwind after a day of skiing. We especially loved the hot tub, it was the perfect way to relax after hitting the slopes! The space is peaceful and private, and we enjoyed exploring the walking trails and the pond. The cabin was well-stocked with everything we needed, including coffee, spices, and even a Roku TV for when we wanted to unwind indoors. Overall, it was a fantastic getaway, and would visit again!

We had a wonderful time staying at this Airbnb last weekend! The location is unbeatable, just 10 minutes away from the ski resort, making it incredibly convenient for anyone looking to hit the slopes. It was the perfect place to relax after a day of skiing. The space was comfortable and well-maintained, and everything we needed was provided. I highly recommend this place to anyone planning a ski trip. We’ll definitely be back next time!

We stayed at Shahrzad’s place during the big snowstorm on Family Day weekend. We were a bit worried about what would be available for us to use but when we pulled in, the driveway and pathways were shovelled for us so it was easy to drive in and walk to the games room and hot tub. They also provided a shovel if needed too. The place was absolutely wonderful and so cozy. You can really tell they put thought into designing the space. My partner and I had a great time staying here. There is plenty to do, we loved the hot tub! It would’ve been even better in the summer I’m sure! The place was spotless and we had everything we needed in the kitchen as well. The bed was super comfy as well. There are 3 fireplace going so it was super toasty despite being snowed in. We will definitely be back again! 😊

This was my third stay at Kris's Airbnb, and I’ve always appreciated the place and overall experience. The home is comfortable, well-equipped, and in a great location, which is why I’ve returned multiple times. The outdoor hot-tub and sauna, home layout and multiple bedrooms & bathrooms are a big plus for our family.

Beautiful property on Lake Simcoe with more than enough room for everyone we absolutely loved our stay and requested to stay longer but unfortunately it was committed to other guests. Great hosts, great communication. This property is the place to stay if you are looking for a spacious, lakefront property with privacy in Innisfil which is very hard to find. Highly recommended!

This place was over and above what we had hoped for. The amenities were great. We didn’t have to go anywhere. The entire family was entertained with all that was provided at this location and we thoroughly enjoyed a little family getaway. The pool table, air, hockey table, indoor sauna, and outdoor hot tub plus all the games provided. The house was very clean the kitchen had everything you needed. It was wonderful.

The cottage is so beautiful and has so much space. Many outdoor activities to do nearby, but we mostly stayed in, the place is equipped with all the things you need to have the perfect getaway. We loved the hot tub and sauna! The hosts were amazing, always proactive and responsive! Will definitely be back! :)

We had an amazing stay at this cozy cottage for the weekend! It was beautifully decorated, super clean, and had everything we needed. The peaceful location was perfect for relaxing, yet close to nearby attractions. Our host was thoughtful and communicative, making sure we had a great experience. We can’t wait to return!

My group and I had an excellent stay at the cottage. The lake is beautiful and the property is as well; inside and out. The location is quiet, yet not too secluded, making the overall experience very peaceful. The home was also very clean, functional, and had even more amenities than we were even expecting! Definitely would visit again. Thanks Jenny and Bob!

Our family had an enjoyable Thanksgiving weekend at Carol's property. The cabin was cozy and charming, the bunkie was super cute and the deck and fire pit were amazing spots to hang out at. It's a short walk to the water and a convenience store/lcbo. Our only issue was that we didn't stay long enough!

We absolutely loved the cottage it was perfect for our week at the beach. The beach itself was just steps away and was absolutely beautiful with calm,clear water and friendly neighbours. There is a strong sense of community in the area. We really loved the outdoor shower which was a family favourite. We will defiantly come back to this cottage again and again if we can.

We had an amazing Christmas stay at Amanda’s beautiful cottage! The snow made the experience even more magical, though we can imagine it being just as stunning in the summer. The heated jacuzzi overlooking the serene view was a highlight for us—it was the perfect spot to relax and unwind. The cottage is incredibly private and exclusive, offering the peaceful retreat we were looking for. The house itself is spotless, cozy, and well-maintained. Amanda’s detailed instructions made navigating everything in the home so easy, and we appreciated how thoughtfully everything was prepared. The place had everything we needed and more. We highly recommend this cottage for anyone looking for a perfect getaway. Thank you, Amanda, for hosting us!

Second time staying at Rachel's- lovely cottage and a great location. Rachel was extremely helpful and easy to communicate with. Thanks again!

It was a great stay with family! We got to walk around, get in the hot tub and play games. The place was clean and comfortable. Great for a winter getaway but I'm sure it's beautiful all year round.

We really enjoyed our stay, the cottage was really clean and loaded with all amenities needed. Would definitely stay again

We had a wonderful stay! The cottage was so cute and cozy and had everything we needed! We had lots of snow during our visit, and loved getting to enjoy the peaceful and private property. We even dug out the campfire pit for a winter fire! Even with all the snow, we were warm and comfortable, with the portable heater coming in handy to warm up after trekking through the snow! Jaclyn was so thoughtful and helpful as a host! We were very well taken care of! I would highly recommend staying here if you want a relaxing, peaceful, and cozy getaway surrounded by nature!

From the moment we entered Haolin’s cottage, we felt like we were home. The place was spotless, the kitchen had everything you would require, and the sofa and chairs were very comfortable for lounging. It is very close to the Wasaga Nordic Centre (3.2 Kms), which has cross country skiing and snowshoeing. The wonderful Baker’s Bench is only 1.5 Kms away and a Tim Hortons is almost beside it. Coffee, sweets and outdoor sports are a heartbeat away from this beautiful cottage. We had a perfect time and will definitely be back.

It was such a nice place. It was very homely and spacious. The kitchen was so well equipped. The host was very responsive, helpful and accommodating. I would love to come back in summer as well.

My wife and I had a beautiful, peaceful weekend. Fere is a delightful host and the property is gorgeous. Close enough to Orangeville but a silent oasis. Thanks again!

We had a lovely stay. The cottage was clean and well cared for, and the beds were comfortable. Beautiful view and the hot tub was great after a day of skiing! The hosts were very responsive and answered any questions we had. We would recommend to anyone staying in the area.

The cottage was absolutely worth it - a great price for a great find. It's a private place, very spacious with lots of amenities. Our hosts were very clear with what is included versus what we need to bring and extremely responsive. They were nice enough to let us check in a little earlier as well which was very helpful. I would recommend this property for a weekend getaway.

The place was absolutely wonderful cozy, beautifully designed, and incredibly inviting. The interior was aesthetically pleasing, making it feel like a home away from home. The kitchen was well-stocked with everything we needed, and there were plenty of games and movies to keep us entertained. The attention to detail and thoughtful touches made our stay even more enjoyable. I truly loved this place and am already looking forward to coming back in the summer! Only thing I had an issue with is the poor signal and a bit of a scary location at night.

We enjoyed everything about our stay! The location is beautiful with so many options to explore - canoe, kayaks and paddleboards, and also relax - indoor sitting area with a great view, back deck, dock and fire pit. The cottage is incredibly clean and comfortable with everything you need (and then some) provided. Highly recommend booking this cottage!