Family-friendly vacation rentals in Wilton

Great location. Easy check in and out.

This home was perfect for my siblings and their kiddos to meet up for a nice long weekend. Kerry made us feel very welcomed and was super responsive when we had questions. The sunroom was one of my favorite places in the house. The kids enjoyed playing both outdoors and indoors. The neighborhood was quiet and the kitchen was stocked. Just a short drive to the mall and plenty of places to eat. We would gladly stay again.

Paula and her place are absolute gems. Communicating with her felt like talking to a friend whose place I was going to be staying at, and it felt like that when we arrived as well. I loved the art and thoughtful touches in each room, and our large group felt cozy yet everyone had their own privacy. The space is actually much larger and more beautiful than the photos even convey! The private trails were stunning and magical— I walked barefoot on the carpet-like moss covered forest paths leading to a Stonehenge-esque clearing with giant boulders. The deck and outdoor space is lovely and has stunning views. So peaceful and quiet with some surprise owl and hawk sightings.

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!

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!

It was great. Everything was the complete opposite of what I expected

We had a lovely weekend at Claudine's. The property is serene. The house is very well equipped and comfortable. We also loved having the sauna. We wanted to grill, but propane was not included in the grill and incurred an extra cost or we had to bring our own tank. For the price and nature of the house, including something like this seems fair. All in all we had a wonderful stay.

Noel was an incredibly gracious and friendly host, providing us with everything we needed for a great stay in her apartment. The apartment itself is so cozy; we particularly enjoyed the library room and exploring the hundreds of titles Noel keeps there. I would recommend Noel’s apartment to anyone that is making a trip to New Haven.

Viviana's place was the perfect stay. It was incredibly clean and included everything you could need. We traveled with our 1-year-old and there was a pack-n-play already setup for him. We felt safe, welcome, and really enjoyed our stay. We appreciated the private entrance, private parking, and clear/detailed instructions. I cannot recommend it more.

Jonathan's place is great. It is historic while having all the modern convenience. Jonathan was a great communicator prior to arrival and with local recommendations once we were there. We had a great experience.

The place is wonderful, had a great cozy stay, the beds are comfortable. Would recommend if you’re looking for a place that’s close by all the restaurants and attractions.

Great place to stay while visiting West Point Military Academy. Highly recommended. Great host

Perfect place to stay in for the weekend. Beautiful view, terrace is one love. The house is even better than at the pictures. Definitely would love to come back again. Thank you for flexible check in and check out.

I chose Marlene’s lovely spot primarily because it was in a location convenient for short trips to visit family and friends in Wallingford, Middlebury and Middletown while on my way south from New Hampshire. The peaceful, quiet surroundings along with a spotless, well-appointed accommodation made it very appealing: highly recommended.

My husband and I had a great stay. James and Rose are super helpful hosts. It’s a great place to relax and enjoy nature. Walking distance to a lovely park they recommended with tons of hiking trails and very quiet.

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! ☺️

Robert was an awesome host! Super easy to communicate with and made check-in and check-out a breeze. We even got to meet him he made balloon animals and did magic tricks for our kid, which was the sweetest thing ever. Seriously such a down-to-earth, kind person. The neighborhood was quiet, cute, and felt really safe. The house was beautiful and way bigger than we expected! We had everything we needed and felt totally at home. Definitely planning to book with him again!

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

Gaby’s place was clean and comfortable! She is very kind and it was exactly what we needed for the week. Her check in instructions and directions were thorough and the home is in a beautiful area. Already have our next stay booked :)

Truly home sweet home. Just walk in and relax. Fully stocked kitchen including milk, eggs, butter and pastries so no need to rush out to go grocery shopping. Convenient to New Haven yet completely quiet neighborhood for resting and taking walks.

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!

The space is adorable, and we loved the history of the rental and the community. The location was perfect for us—close to everything and secluded all at the same time. Also Jeff is an amazing host and made us feel welcome/at home. The next time we have to head to NY for a family visit we will definitely try to stay here again.

Great home and host. Responsive to inquiries. Would recommend!