Kid-friendly holiday rentals in Dutchess County

My stay at Cynthia‘s house was wonderful! It was a perfect small private getaway after going to a conference each day for long hours. The snacks were such a sweet touch and much appreciated as I had very early mornings and didn’t have a lot of time to make breakfast. I will definitely be staying there again if I’m in the area for work in the future.

Nestled on a quiet road, you’ll find your little hobbit hole. This property is beautiful. Cozy and comforting. If you’re a fan of the LOTR, then I highly suggest staying here. It has everything you need and amazing attention to detail and the series. Your adventure awaits!

Traveled back to this area for several New Year’s celebrations. Extremely convenient to Buttermilk Falls Farms and nearby restaurants. Will stay here again in the future.

This was a great location and great stay for my weekend getaway with friends for my birthday. The layout was not what I expected but overall worked for our purposes. Location was most important and this definitely delivered! Overall really great stay and Eva was very responsive!

Great stay! Our host was very responsive and easy to work with. Everything was as expected and we are so grateful to have stayed so close to our son’s boarding school.

We had an absolutely wonderful time. The house is beautiful and full of so much character and charm. So many lovely touches by the hosts leaving us a generous and lovely gift basket upon arrival. Communication with hosts was amazing and they ensured that everything was perfect for the entire weekend. The home was comfortable and a perfect place to relax and just a short drive or walk to Millbrook which had everything we could need. Definitely would recommend and hope to stay again myself.

The long table and open living room was the perfect place to catch up with a group of old friends. We loved the space so much we decided to stay in and enjoy each other’s company, instead of going out. The place was beautifully decorated and spotless, and we caught a gorgeous sunrise off the deck!

Words simply cannot describe how magical this Airbnb experience was. a group of friends and I passed the hours marveling at the gorgeous art and curated knick-knacks - the home itself an endless source of fun. - like an interactive museum! Thats without even mentioning the property, the pond, the waterfall, the chickens, tire swings and HOT TUB! Truly a miraculous experience, would highly recommend and we will absolutely be returning.

Chris' place was even more beautiful than in the pictures. Location is perfect, within easy distance of the beautiful Kingston waterfront and nice restaurants. The area is quiet at night and felt very safe. Check-in was smooth and we had everything we needed. We'll definitely be staying there again on our next trip to Kingston.

We stayed at Michele's quaint Poughkeepsie condo for two nights while our daughter was checking out Marist University. Fit our family of four perfectly. Beautifully decorated in antiques and art and felt like you were staying with a friend in the area. Whole place was very clean and the kitchen was well stocked with whatever you might need to cook. Michele even left some snacks for us when we arrived, which were invaluable after traveling all day and arriving super late with two hungry teens. Only downside is I didn't realize Poughkeepsie's downtown is not a thriving one. Most restaurants and shops are not nearby; they are scattered throughout the city (Check out Kelly's Bakery for sure!). Nice to have a car and there is easy free parking on the side of the house. There are a couple hotels in the area, but also not near much, so Michele's place was perfect as we were not looking for hotel vibes.

lovely place in great location. stream just behind the house. really easy instructions to get in. a bit of road noise in the front bedroom but not too intrusive.

A home away from home. A lovely stay as always.

Lynn’s home was cozy and beautiful on a quiet street right next to the main street through Beacon. A great stay 💚

We had such an amazing weekend, the house is perfectly located, so comfortable and beautiful.

We had an amazing time at Ann Marie’s place! The apartment was spotless, beautifully decorated, and had everything we needed for a comfortable stay. Snacks and beverages were provided and the fridge was stocked completely. The location was perfect. It was extremely close to the main attractions. Ann Marie was so welcoming and responsive, making sure we had everything we needed, and even provided great local recommendations. Highly recommend staying here, and we’ll definitely be back the next time we’re in town!

We have been to Dave and Trish’s several times. It is our go to place when we are in the area. Always clean, always welcoming and always just right. The home is spacious and the neighborhood is lovely. All of the amenities listed or hallways available. A welcoming and wonderful Airbnb.

This was the second time my wife and I have stayed at Michelle's apartment and we were both very happy with our experience. It is one of the cleanest Airbnb's I have stayed in and Michelle is a really responsive and thoughtful host. We would certainly stay here again!

Dan's place is the most thoughtful airbnb we've ever stayed in. He's literally thought of everything and provides answers before you've even thought of the question. Made it a wonderful weekend. Thank you!

We originally booked the cabin in Accord, but due to the extreme weather and cold the pipe frozen and we ran out of water but Matthew and Darla were quick to find a solution and move us to their other location in Kingston. It was not exactly the "in the woods" feeling we wanted but also we have 2 small kids so it was best to stay in Kingston and make sure we had all we needed for our stay. The communication was extremely good and quick, they were on top of everything. The place in Kingston is actually quite nice, it was quiet, close to the water and some nice places we love to go like Rosie and Half Moon donut. The house had everything we needed including kids plates, bowls, cuts, a high chair and GAME!!

Henry and Jorge could not have been friendly and more accommodating! The location of their place was extremely easy to find and super convenient to Saugerties, Kingston, Catskill, Woodstock, etc. Their bed was super comfortable and the room was well equipped with everything we needed. Would definitely stay here again!