Family-friendly vacation rentals in New Canaan

We loved staying at this home - it was the perfect place for our group of ten. The outdoor space was definitely the highlight, with the pool & spa being our favorite part of the trip. The only thing to note is that we weren’t supplied quite enough toilet paper or paper towels, though I did not reach out for more - It was the last evening when we ran out and we were leaving early the next morning. The trash requirements were a surprise after booking, but going to the transfer station was easy enough, and it is listed on the house rules. Overall, an excellent stay and would absolutely return!

We loved our stay. They provided everything you need plus more. So comfortable, lovely ambiance and the sauna and hot tub were fantastic. We came on a rainy day and still had a great time. Location is 10/10. Loved the calmbucha. Highly recommend!

We had a fantastic girls weekend in Southampton and loved Anthony's cottage. It was so beautifully decorated and cozy. We throughly enjoyed mornings with coffee and books in the sun room.

Victoria's place was wonderful! It was spacious and comfortable and gave our family plenty of room to spread out and enjoy our visit. Victoria was a very responsive host and made check in and check out stress free and easy! There was ample parking for our cars and the house was private - it was the "house behind the house" so we weren't subject to busy traffic noise on the street. (Got a little confusing for DoorDash drivers but we worked it out :D). I will book this same place next time I am up for an extended weekend with the family. Highly recommend!

My family of 8 adults needed a place to stay near a wedding at Glynwood. This wonderful spot was minutes away from the farm and town. The number of bedrooms and bathrooms gave everyone the privacy desired while the well equipped kitchen and living rooms had plenty of space for gathering. The house and land are beautiful, including the trail. Paula was easy to communicate with and my whole family felt comfortable and happy with the spot. Highly recommend!

Abagail was very helpful in getting settled. The house is full of interesting antiques and paintings. There was a wonderful view of the Litchfield Hills and a lot to do outside. It is rustic but it has every convenience of home. Great shower. Must have been a barn but now it is a museum of Art Nueveau treasures and stained glass. Very peaceful and slept great.

My fiancé and I stayed at Lambs hill to celebrate our anniversary. We had the most wonderful time. The views are breathtaking. The wrap around deck with jacuzzi and hammock made our stay calming and serene. I loved seeing the horses and donkeys throughout the day. They made the experience even more special and unique. Charlotte was super responsive and accommodating. We took cabs to Main Street at night for dinner and drinks and it was so close and convenient. I left my heart in lambs hill and can’t wait to return one day.

Roma was very sweet and welcoming showed us where everything was. We even got to meet beautiful grandchildren. The space was very beautiful and glad it offered parking. This will definitely be saved as s favorite for future bookings

We had a lovely stay at the Milk Barn property. We loved the authenticity and sustainability that were thoughtfully incorporated into this place. The peaceful, serene atmosphere and greenery made our stay very tranquil. We had a chance to chat with the owner—what a lovely couple! We will definitely recommend this place.

Our stay here was excellent. The guesthouse is beautiful and very conveniently located. It is a short walk to the train station and near many restaurants and a grocery store. Also, the host was very responsive. If I return to Yonkers, I would happily stay here again.

Kate and Daniel are wonderful! Their beach cottage is a must for all families. The farmers markets within 2 miles have all the produce you need, while the fish markets within 5 miles have all the fresh caught seafood you need! There are several New York vineyards nearby and I’d recommend traveling to all the local towns like Greenport, Shelter Island, West/East/South Hampton, and Montauk to see how each one has its own identity. Overall, my wife and I loved our stay at the cottage and we spent most are days laying on the back porch with the beautiful views! Also, great kitchen for cooking and backyard grill with a view.

We absolutely loved our stay ay Susan's place. We were celebrating our ten year wedding anniversary with our dogs and it could not have been more perfect! The private pool setting, access to the rail trail that leads directly into town, the giant windows bringing the outdoor greenery inside, the Frida Calla 500 piece puzzle, the I pad hooked up to a lovely sound system, I could go on and on. We rarely visit the same place twice, but we made need to break that streak with this place.

This was our FOURTH stay with Erik at his place. That should say something right there. It's our go-to hideaway when we head for the Hudson Valley. The location can't be beat, right alongside the Wallkill River just outside of New Paltz. We've spent hours outside by the water sipping our coffee and sharing a glass of wine. We've experienced perfect Fall weather, really hot days and some rainy days, and it's still the place to be. The view is literally a million-dollar view, and you can see the tower at Mohonk straight down the river from the house. Erik is very quick to respond, the interior of the house has been consistently immaculate and exudes coziness. During hot weather, the AC is more than adequate and the hot water in the shower perfect for two demanding runners. We look forward to our next stay here! Brad & Jane

I loved my stay here!! The backyard area is absolutely stunning!!

We had such a great time that we ended up booking another stay on our very first day! We came for Father’s Day weekend and were really impressed by how many thoughtful touches and recommendations were listed in the guest handbook. The dog beach was a huge hit with our puppy, and we had a blast. Thanks for helping make our vacation so special!

We really enjoyed our time at Elizabeth Jane's place. The home is spacious and quaint, with nice furnishings, a tasteful colonial feel and easy access to downtown Litchfield and the Berkshires. The bucolic setting is lovely - scenic, relaxing and peaceful.

The Barn was very nice and peaceful. It was close to restaurants and family. Suited us and our dog very well. The property is right next to a golf course and there is a deer living on the property. We saw a fox one morning as well. We really enjoyed staying at the barn.

Fantastic property that is both in a quiet area but you can easily get to almost anywhere in 20 min or less! Had a fantastic time despite the weather. Wish the pool was heated and that there was a larger TV upstairs and in the bedrooms (on rainy days and at night it would be nice to unwind to a show). Great acoustics in the house for the bose sound system and wonderful home layout. Could use some new pillows throughout, especially on the beds, but none of this impacted my stay in such a way that it still wasn't fantastic! Michael was always there to answer any questions or deal with concerns and I certainly felt taken care of and treated like family. This home is larger than most, but feels like you are right at home. I would love to stay here again next summer!

The pool house is so cute and the outdoor patio is gorgeous and the perfect place to relax. Great place to stay if you want to stay near New Haven but also want to enjoy quiet away from the city. Sue is a responsive and very generous host!

Fantastic absolutely amazing experience. Jaime was beyond great when it came to professionalism and kindness and responsiveness. Super clean beautiful apartment didn’t miss a trick when it came to anything you might need. This was a top-notch experience. Amazing customer service, beautiful location. Beautiful pool and spa overlooking the ocean We will definitely be back.

Christine's place was nice and clean! We especially loved the fire pit and the pool. Upon arrival of the AirBNB Christine was waiting to meet us and show us around. This was something that was new to me in my AirBNB experience, but it was honestly so nice and so was she! Christine let me know that I could communicate with her for anything that was needed and asked for recommendations to make her place better. This place was so well-equipped, close to everything and it comfortably fit me and my 6 other friends! I would definitely book again with Christine.

We had a lovely stay at Roger and Amy’s place. The location was great - close to Southampton, a short drive from Sag Harbor etc. The home is charming and comfortable. The kids loved the heated pool and spent hours in it every day. Roger and Amy were also super responsive, with advice and help when we needed it including with a very sweet gift for our 3 year old whose birthday we were celebrating. All in - a phenomenal time!

Alice’s place was great! We’ll be back again for sure.

We had a lovely stay at Eric's home. The home exceeded our expectations and we felt right at home. The decor was warm and inviting. Everything you could possibly need was in the stunning, modern kitchen. The beds were all comfortable and we slept very well. The property was very peaceful. We enjoyed seeing deer, turkeys and hawks each day. The fixtures in the home were modern, clean and high-end. It was great being so close to Greenport with it's wonderful restaurants and shops. We can't wait to return.