Holiday rentals with outdoor seating in Dufferin County

To say we lucked out finding this home and its owners is a massive understatement. From the moment we booked to the day we departed—and even after—Mike and Kim went above and beyond to make our multi-generational family stay and 50th anniversary celebration a complete success. We’re so grateful to have found them. Initially, we were just planning to enjoy their beautiful, well-appointed stone farmhouse, set on immaculate grounds with a stunning saltwater pool. Then we learned we could rent a separate event space for the celebration—a gorgeous greenhouse at the top of the vineyard. To top it off, Kim and her family offered to cater the event. Everything was flawless. The guests were overjoyed with the food, the setting, and the whole experience. Most importantly, our parents had the most epic anniversary we could have imagined. Thank you for making it all possible. We’ll be back any chance we get—and we’ll be recommending you to everyone we know! !

This was a wonderful place to stay and was exactly where I needed to be after long, hectic days. Sherry is a great host - very friendly, accommodating and making sure I was comfortable. Her gardens make it seem like paradise when you walk from the driveway to the private entrance - love love love the lilac trees beside the parking space ❤️ This felt like I was staying with a friend rather than in a stranger’s place. Thanks Sherry for all your hospitality!

We had such a wonderful time staying at John’s place—it honestly couldn’t have been better. The home was gorgeous, spotless, and felt so warm and inviting. You can tell a lot of care went into making it a space where guests can truly unwind and feel at home. The private pool was a dream. Surrounded by trees and completely peaceful, it felt like our own hidden escape. We spent hours swimming and lounging by the water, and since it was deep enough to dive, it added that extra bit of fun we didn’t expect but absolutely loved. John was an incredible host—super responsive and kind. Any time I had a question, he got back to me right away and made sure everything went smoothly. It was so reassuring to know he was just a message away. If 10 stars were an option, we’d give them in a heartbeat. This stay set the bar so high, and we’re already talking about coming back. Huge thanks to John for making it such a memorable getaway!

My family (5 adults, 1 child, 1 infant) came to town for a wedding and were So Lucky to have stayed in this Beautiful home for 5 days last month. The house is spotless, modern, well maintained, and so spacious with plenty of very comfortable, well appointed rooms (4 upstairs, 2 basement) and bathrooms (2 upstairs, 1 basement, 1/2 main floor). The cozy living room is equipped with ample seating and board games. The dining room is large with a great table easily accommodating 10 people. The kitchen is huge and we found all we needed there. There is also a laundry room and mud room leading to the Fabulous hot tub in its own "house" on the outside deck. This Beautiful house is situated on a Gorgeous piece of property with Incredible views all around. The co-host, Brendan, was easy to communicate with and gave us clear instructions. This was the Perfect place for our day-trip into Toronto, "hiking day" in the Island Lake Conservation area, and relax-at-home day, before the wedding.

We had a wonderful stay at Jeff’s lovely Airbnb over the weekend for my friend’s son’s wedding. The home was spotless, beautifully decorated, and had everything we needed to feel comfortable and relaxed. The host was incredibly welcoming and responsive, which made the experience even better. The location was perfect—close to the wedding venue and local amenities, yet peaceful enough to unwind after the celebrations. We especially appreciated the cozy touches that made it feel like a home away Thank you for helping make such a special weekend even more memorable. We would absolutely stay here again!

I recently stayed at Jer’s Airbnb with a group of seven friends, and we had an incredible experience. The amenities truly made the stay unforgettable. We spent hours enjoying the pool table, foosball, darts, and old-school arcade machines. The private sauna and jacuzzi were perfect for unwinding, and the outdoor BBQ and fire pit setup created the ideal space for evening hangouts. Everything was spotless, well-organized, and located in a quiet, safe neighborhood. Jer was an excellent host, very responsive and clearly committed to providing a top-tier experience. I highly recommend this property to anyone planning a getaway with friends or family. We had an amazing time and would absolutely stay here again. Thanks, Jer! One thing worth highlighting is that the pictures don’t do this place justice. As great as it looks online, the property is 100 times better in person — more spacious, more comfortable, and filled with thoughtful touches that aren’t fully captured in photos.

It was a great location and hosted a large group. Very nice place in a remote area, giving us the feeling of an outdoor oasis.

We had a great experience renting this home. We stayed for 2 months. A lot of space for entertaining/ bonding with family. Really enjoyed having 2 separate kitchens. Very spacious house and huge backyard. Everything was perfect.

Great place, very peaceful and clean. Home from home. Great hosts who couldn’t have been more helpful.

Colin met us when we arrived and gave us a thorough tour of the rental unit which was exactly as advertised with lots of natural light. The location is out in the country in a beautiful rural setting and only 10 minutes outside of Orangeville and access to restaurants. Unit is very well equipped and Colin and Beverley graciously provided us with a bottle of wine to enjoy! We stayed two nights and while we didn’t have a chance to take advantage of all the amenities and hiking trails on the property we certainly hope to in the future.

This was the second time we stayed at one of their listings and again, it was a lovely stay (stayed in the basement unit previously). The home was beautifully furnished and offered enough space to be comfortable in. The extra little things they do (providing a few toiletries, a welcome sign, and chocolate) adds an extra level of consideration I appreciate as a guest. We enjoyed our time and the space we had. All the kudos to the hosts, Andrew and Amee; we would choose to stay again at any of your listings!

Stacy’s L&S Comfy Suite was perfect as a base for some Bruce Trail hiking. It was welcoming, spotless, well equipped, and good value. We would highly recommend.

I loved my stay in Orangeville. This airb&b was clean and spacious. The host was proactive in the communication and made sure to help in anyway. Thank you!!

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! 😊😍

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!