Family-friendly vacation rentals in New Canaan

Captain Dan's artists retreat is a one of a kind, beautiful space to unwind. We celebrated New Years here and had a truly special time. Highly recommend to all those looking to take a few days away from the hustle and bustle to reconnect with nature, art, & a hot tub!

This is the 2nd Thanksgiving weekend we spent at Deeanna's. Her home is beautiful, comfortable and each detail is thought though in the best way. Deeanna went above and beyond to accommodate my family and we are so grateful to her. The kitchen is perfection and the bedrooms are lovely and comfortable. The scenery and views are breathtaking. Overall, this home is a total gem. Thank you, Deeanna! We hope to come back next year!

This getaway was very last minute and there was huge importance on it because I needed some time away and because I had never booked an Airbnb before. I wanted to make sure that my family and I were able to be someplace peaceful and have a really good time and Brian’s home provided just that. The stay was so much more than we expected and Brian was absolutely amazing. He’s super responsive and accommodating. Hoping to stay here again in the near future!

I went for my boyfriends 25th birthday it was absolutely stunning from all of the art everywhere in the house and outside! We stayed in the sauna from when we got there till late at night it was an absolutely wonderful experience even just for a night!

This is a beautiful place and exactly what my wife and I needed for a long weekend away! The barn is so cozy and we felt right at home . The hot tub was a nice treat on the cool evenings and the beautiful view. But by far the best part was the animals living below us that we could give snacks to throughout the day and see through the living space windows. Would definitely recommend this to anyone that loves horses and donkeys!

We enjoyed a beautiful early spring stay on the farm with a group of 7 ladies, gathering for a chill bachelorette weekend in Cold Springs. The farmhouse was super cozy; great for cooking, crafting, games, tea time, outdoor wine picnics, star gazing at night in the hot tub and making friends with the chickens! A great retreat spot for groups with all the amenities!

Perfect location — it’s directly in the middle of Minnewaska State Park and downtown New Paltz. Stargazing in the hot tub was a perfect way to relax after a long hike.

This was such a nice space and Lisa was a nice and accommodating host. This place is full character and wonder. Very artistic color energy in this place. We started my daughter’s 18th birthday celebration here with what is her last sleepover with friends. The hot tub, steam room and sauna were the first things and last things used. They enjoyed it so much! Thanks for your hospitality Lisa. If we ever need something like this again. We will be sure to look you up! Blessings

The Farm House was adorable! The beds were very comfortable and it was very clean! Great history of the home and farm too! Rescued and restored and saved the land from condos! ❤️

What a perfect place to stay! We were very comfortable in Hazel’s little retreat… we slept well in the king sized bed, had plenty of hot water, loved the bucolic green space and the creek nearby. Our dogs had great walks under the canopy of huge trees surrounding the property. I especially enjoyed watching and hearing the ducks, geese and swans across the street as they paddled to the pond! Thank you, Hunter for providing a perfect getaway spot for your guests!

Mahmoud's accommodation was more than we could have wished for, it was perfect and had the most incredible views of the Hudson River and surrounding mountains. Mahmoud was very responsive and was able to answer all of our questions and fulfill our requests. We highly recommend his home to anyone else that's interested and we would love to make a trip back sometime in the future!

Erik's place is a Gem. It is located in a beautiful area close to New Paltz and Gardiner. The home was amazing, clean and well equipped. Erik and his father George were very responsive from the booking process, follow-up, directions to the place and took care of our requests promptly.

Was in the area to visit family and this was a perfect location for me. Had just what my family needed to have a great weekend

Very nice place and location is amazing. We were grateful that our host provide some basic amenities - coffee, shampoo and condtuoner, etc. Made our visit easy and very pleasant. Thank you!

Our stay in the Fairfield University area was absolutely delightful! The home was cozy, impeccably clean, and filled with thoughtful touches that made us feel welcome from the moment we arrived. The location was perfect, close to family and friends yet wonderfully quiet and peaceful. Bill & Lois went above and beyond to ensure our comfort, I especially enjoyed the chocolates (shhh) just don’t tell my cardiologist. Sheila loved the ceramic dish. We couldn’t have asked for a better experience and look forward to returning. Thank you

The house was absolutely beautiful well cap very clean and organize. I rented this place for Christmas so there was ample items that we found usable to make a beautiful Christmas table presentation. I would highly recommend this place again. Thank you Martha for your hospitality.

We had an amazing stay at Sally’s place in Bethel! My fiancé and I visited CT for the first time to celebrate my birthday and go to a convention nearby. This cottage was perfect for the two of us. The host was very responsive and accommodating as well! The cottage was in pristine condition, the house manual was very easy to follow, the recommendations were great, the scenery was out of a movie, and my favorite part was the hot tub in our restroom which was perfect after a long day! We had a great time and would love to come back again! Thanks for your hospitality Sally! ☺️

Place was perfect! Clean & made our Holiday stay in the beautiful Hudson Valley a wonderful experience. We loved the personal touches the house offered and we will be back

We had a wonderful stay. Cute and comfortable house in an amazing location. Very comfortable for a family of 4.

Susan’s home is wonderful. The layout of the house was perfect. We had my elderly parents with us and we did not feel at all as if we were on top of each other. The kitchen was also perfect for a small group to entertain and was loaded with amenities! Everything was spotless and exceptionally clean. It’s very close of the village of New Paltz (3 min. car ride) where the restaurants and shopping is located. We also had a nice view of Mohonk Mountain! All in all it was a perfect and peaceful getaway weekend in the mountains!

Michael was a great host, friendly, flexible and helpful. The house is beautiful and has all the amenities you would expect. We loved staying there and would definitely like to stay again.

We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!

Had an absolutely wonderful stay! Location is perfect and Jaime was incredibly friendly throughout!! He let me know that they had everything we would need.. but as a self-described obsessive packer I didnt listen. He wasn't kiding! They had beach chairs, umbrellas, and everything else you need for the perfect beach day. I brought an entire wagon of stuff and used one bag. It really is an awesome little find!!

This wonderful antique home is in a Beautiful spot in the heart of Litchfield CT, and a delight early spring when the fields of daffodils awake! This unique 1793 house has a great view & sunset, fireplace, simple spa/gym making it a gem even when the pool is closed. Nearby the town with lots to offer and local farms for food shopping too. What’s not to love 💛 Bonus is a great host offering a home that is in touch with the realities of rentals, pets and people -not picky, precious or punitive. Happy to recommend and return! Thank you Elizabeth!