Family-friendly vacation rentals in Wellington

We had a wonderful stay for 5 nights at Cheryl & Kyle's. Beautiful sunsets, dips in the lake, hot tub, sauna, well equipped kitchen, AC, ... A great perch to enjoy what the county has to offer! Hosts were quick to respond to any questions we had. Highly recommended!

Carola was very responsive whenever we needed to message her, which wasnt often. Her air b&b had everything we needed for a comfortable stay while we were 4 hours away from home. The grounds are beautifully landscaped and show her passion and pride for her property. There were a couple minor hiccups that were out of anyones control during our stay and she rectified them right away while also keeping us informed, and were not inconvenienced by the hiccups at all. The condition, location and her communication made our stay totally worth it. We rented the hot tub and it was a beautiful treat with the typical May 2/4 weather fluctuating. Carola added in thoughtful comforts hanging at the entrance to make our stay that much more enjoyable, it was thoughtful, sweet and appreciated. This is a must stay at location. We will definitely be back!

Our stay was great and Fedora got back to us very quickly about any questions we had! Very great space and property, would definitely return :)

We stayed at the house for a family long weekend in May 2025. The property was as described and well appointed. A great base to visit the County.

We stayed a weekend in May. The place is immaculate and the view is beautiful, exactly like the pictures! Because it rained intermittently and cool we didn’t get to use the outdoor amenities including the firepits. The trail towards the back of the property around the pond was washed out due to the amount of rain we have been getting. It didn’t dampen our weekend though but we look forward to coming back and explore. We enjoyed outings like brunch in Sterling and a water buffalo farm 3 minute drive from the house which had great gelato. We also walked around the main road the house was on and met a few friendly neighbours. The hot tub was great and so was sitting on the deck having a drink and taking in the beautiful scenery. The beds were comfortable and each bedroom had their own bathroom. All amenities were there including the kitchen - we cooked 2 dinners and found everything we needed. Overall a great choice if you are looking for a place to relax with a view, this is it.

Excellent accommodation. Beautiful property.

We had a great weekend stay! Josh’s place had lots to do and offered a great amount of space for board games and meals! Great location and very close to stores and the downtown core. Would highly reccomend!

what a beautiful place! it was so welcoming as soon as we drove up the drive way, opened the door and WOW! it was more than we expected with the wonderful large bedrooms, gourmet kitchen and large gathering area to enjoy a meal,play games or lounge on the recliners not to mention the peaceful lakeview right outside the back door to enjoy a morning coffee and just breathe. It was very relaxing and a wonderful time with good friends. We hope to be back one day soon.

We absolutely loved our short stay at Matthew and Natalie's place. It was a beautiful, peaceful environment that really provided a relaxing vacation. Everything in the house was thoughtful and lovely, from the decor to the well stocked kitchen. Would highly recommend and hope to return!

We really enjoyed our short stay in the rather large apartment in Picton. The location could not be better. The view out the kitchen window was lovely with the fall color and the little hint of the harbor that was visible. We enjoyed watching tv in the evenings in front of the fireplace. Definitely recommend!

Lovely little private cabin on the side of Lake Ontario!

Such a cozy space that accurately reflected the Air BNB listing! The location was approximately 15 minute away from downtown Picton by car which was a major plus for us. Sally was proactive with her communication with us and always quick to respond to our messages. We arrived late in the evening and there was limited lighting along the long driveway which made it slightly more challenging when we first got there but this wasn't a huge deal. Sally has a large sign with arrows indicating for you to follow to the cabin & where to park your vehicle which was helpful. The cabin was well-furnished and clean. The bed and seating were very comfortable. Mother nature wasn't completely on our side for our weekend getaway as it rained and was slightly too cold for us to make use of the beautiful screened in porch, the fire pit or explore down by the water on the property. The cabin has a nice remote controlled fire place that adds an extra cozy touch. We would definitely recommend!

We had a great experience at Zev’s place. It was nice and cozy and central to everything that we planned to do in PEC. It was perfect for what my husband and I needed for a weekend getaway. Zev was even kind enough to gift us with a bottle of wine. We would love to return again.

We absolutely loved our stay! The location is perfect, close to services and all the activities around Sandbanks. The property is spotless, very well maintained, spacious and peaceful, ideal for relaxing by the water. The sunsets are absolutely stunning, no need to go anywhere, the show is right there. The hosts are extremely kind and helpful if you need anything. The cottage is super clean, well equipped, and the beds are very comfortable. We’ll definitely be coming back!

Daryl & Karen are wonderful hosts. We enjoy visiting their cabin and bringing our dog with us - there are many options for day trips from there, but this time we just relaxed and enjoyed the serenety of the cabin, the waterfall across the street, going for local walks, throwing balls in the open field for our dog & the fire pit during the evenings. We highly recommend the cabin for anyone looking to get away from the business of daily life for a while, &/or for those looking for a serene visit to the country. Many thanks to Daryl & Karen for helping us have another great stay! We are already looking forward to our next visit!

The coach house was a perfect size for two people. Very quaint. It was pretty well as described, but not quite walking distance to Main Street in my opinion. But it was less than a 5-minute drive to the free parking lot on Mary Street and easy walking to the shops on Main St. From there. Lovely shops & restaurants in Bloomfield & Wellington and wineries all about 20 minutes away. Love the County for a short getaway.

It was a great stay and very accommodating. Kids enjoyed the pool table and foosball indoors as well as the pool and lake outside. The kitchen and view of the lake was amazing. Lots of fishing was done from the docks and petal boat and some paddling from the kayak and paddle board (we brought this).

We just returned from a weekend with our extended family at Crossroads of the County. The home is beautiful, extremely clean and has everything you can think of. Kitchen is stocked with utensils and spices making it easy to make your own food there. The location itself is also a quick drive to anywhere you want to go in the area. We loved how kid friendly the location was with toys for the kids, and even plates and cups + playpen and high chair making it a lighter packing trip for us. We would definitely (and hope to!) return again!

Our stay at the Oasis was wonderful! Tons of space and great pool area. The kitchen is fully stocked and Laura was very responsive. We would stay here again and highly recommend it.

This home is stunning ! Full of country cozy charm with some upscale conveniences and an amazing water view. We booked for a girls weekend away and could not have been more pleased. The location was great! Grant was welcoming and easy to communicate with and the home a beautiful. Would highly recommend!

Heather’s house was a fantastic place to spend the weekend in PEC! The house and property were beautiful, spotless and came stocked with any and every amenity you might need. The location was also great as it was private but still close to many wineries. Heather was friendly, informative and responsive and made the entire process easy. We would highly recommend this property for anyone looking for a getaway in the county!

Kerry and John's airbnb is amazing. It is even better than the pictures. We had an amazing time with 4 adults and 2 kids. We were greeted with welcome wine and a sweet note from them. We all enjoyed the pool and the kids loved the huge backyard to run around. The place was cozy, clean and had everything we could have asked for. communication was a breeze. We would love to return some time.