Kid-friendly vacation rentals in Dutchess County

The home perfectly met our expectations and needs. It was very clean and comfortable. Would stay here again.

We had a great stay at Jodi and Jim's Hobbit House. It was the perfect place for our family to escape from the city and spend a few days in the world of Tolkien. The house was spacious, comfortable and both the interior and the grounds were decorated with great attention to detail. Jodi and Jim were wonderful hosts who made us feel welcome and were very responsive. I highly recommend the Hobbit House to anyone looking for a getaway with a fantastical theme.

Beautiful home. Highly recommend booking both sides of the home for additional space during your stay!

Had a lovely stay, felt very much at home. Beautiful space, you can tell this is a home that has been loved and taken care of.

Sarah and Jonathan- We enjoyed a lovely weekend at The Beech House! The home was so cozy and in a beautiful setting. We looked forward to sipping our tea each morning while admiring the view of the snow-capped Catskill Mountains. Also - appreciated the mid-mod aesthetic and all the natural light pouring into the main level kitchen, lounge and dining spaces! And as Texans - it was a real treat to spend time in the snow 🥰. We will definitely look for more reasons to visit Millbrook and stay at The Beech House again. Thank you! Amy and Ray

Bessie’s place was perfect for a winter getaway with friends! It’s spacious, clean & even better than the photos. There were plenty of games and everything we needed in the kitchen. The fireplace was such a nice touch! The house is located uphill & driveway fit both cars comfortably.

I chose this lovely home to host a teacher training gathering for a few days after a conference in the area. It was a perfect size for our small group. The barn acted as a nice meeting space, and felt spacious with the big doors open! The home is tucked away on some beautiful land, with a waterfall and a pond in walking distance. Cool art all around and eclectic furniture. Would highly recommend!

Margarita’s house is lovely! Great location within walking distance to the village, restaurants, and grocery store. We felt right at home and would definitely stay again. I highly recommend this gem!

Super charming place with lovely details throughout. Very comfortable and well appointed. We didn’t spend much time in the immediate neighborhood but it’s very centrally located and there’s a great coffee shop just down the street that we loved stopping at on our way out for daily adventures.

Nicely rebuilt top (3rd) level of an older home. Easy access via outdoor stairs to 2nd level then enter inside & one more flight to top. Newly constructed private outdoor patio looked great but the weather didnt allow us to enjoy it. Superhost immediately replaced broken coffee maker, caffeine addicted guests were very grateful! Hope to return to the area & will rebook if available.

Mark’s place was wonderful! It was the perfect place to stay for a trip to both get into the Catskills mountains and have the accessibility to the city of Kingston. Great coffee shops and restaurants a close walk away! Would definitely stay.

Ann Marie provided a stocked fridge with juices and water. There are so many little details that made this stay so comfortable. I added some photos of the items she stocks her place with. Thanks again!

Dave and Trish were such excellent and friendly hosts! Always responsive and always helpful! A wonderful place to stay. The entire place was easy to feel at home in. A thoroughly enjoyable stay. We will definitely return!

We had a relaxing stay at Vicky’s place. It is tucked away from the bustle of downtown Rhinebeck, but a 15 minute walk allows easy access to all the great shops and restaurants! We found the location to be a great jumping-off point for anyone looking to explore the Hudson Valley region. The unit had everything we could need, and we felt comfortable and cozy. We would highly recommend. Thanks, Vicky!

Susan was a lovely host. The apartment was very clean and there were lots of small, thoughtful touches that we enjoyed, especially the basket of snacks. This was a great location for the Rhinebeck Sheep and Wool festival. It's not in town, but the little town is a short drive away.

I had a lovely in Miryan's home - the unit was very spacious and equipped with everything I needed, and so well located! I was able to hike Mount Beacon everyday and enjoy all the shops and restaurants, and didn't miss having a car at all. Really would have loved to stay longer, and can't wait to come back. Miryan was very responsive, and the neighborhood felt safe and easy to get around. I also appreciated use of the washing machine and the local coffee she provided, as well as the well equipped kitchen!

Andrea was a great and super responsive host. We loved her apartment and it was a quick walk to downtown Beacon and our pup felt right at home. A perfect spot to explore Beacon without having to do much driving at all. Would stay again.

I had a lovely stay! The Airbnb was spacious and the bed was extremely comfortable. Thanks, Michelle!

We absolutely loved staying here. Great communication and directions. Really appreciated how everything was meticulously labeled, making it easy to figure out where to park and how to find our way inside and to know what light switches turned on what. From the moment we stepped in the door until we left we kept finding fun and quirky decor items to love. Very cozy and comfortable furniture. The bathroom was fantastic, especially the deep spa tub. Close to all the fun downtown Beacon shops and restaurants. Don't miss Barb's Butchery, walkable just up the street. Fantastic breakfast items! Thanks for sharing this great space. We hope to come back for a visit!

I always love staying at Henry & Jorge's place. Great hosts! Very friendly, always responsive and extremely accommodating. The bedroom is cozy, clean & comfortable! It's attractively furnished and include many amenities. Love that they have Netflix and Prime Video for guests now!! Convenient location, easy parking and the seamless check-in are all a big plus.. Highly recommend a stay here!