Kid-friendly holiday rentals in Dutchess County

We felt right at home at this fabulous find. Just 8 minutes from CIA. Cynthia was super friendly and helpful. We are so happy we found this place!

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!

We stayed here for our wedding weekend and couldn’t have asked for a better experience! The house was cute, clean, and comfortable - exactly what we needed during such a busy and exciting time. We especially appreciated how close it was to everything; it made it so easy for us to get around without stress. Eva was wonderfully responsive and kind, answering any questions quickly and making sure we had everything we needed. It truly felt like a home away from home. We’re so grateful to have had such a great place to stay during such a special moment in our lives!

We truly enjoyed our stay at Daniele’s during a weekend ski trip! The home was exactly as described and we did not run into any major issues. The only thing I’d note is for a group of 8, we did not have enough toiletries (i.e., shampoo, body wash) or household supplies (i.e., paper towels) near the end. Aside from this minor concern, we had a wonderful stay; Daniele was extremely responsive and accommodating with our requests. Thank you so much!

What a beautiful location to work for a week. Gorgeous views of the wetlands and birds from the porch and the WiFi kept up with video calls from there as well. House was exactly as described and very comfortable.

We had the most peaceful and rejuvenating stay here! The views were absolutely breathtaking — waking up to such natural beauty each morning was pure bliss. The entire place had a calming, serene atmosphere that made it so easy to unwind and truly relax. My pup loved the large yard. What made the stay even more special were the thoughtful little gifts left for us — such a sweet and personal touch that really made us feel welcome and cared for. Highly recommend for anyone looking to escape, recharge, and soak in some stunning scenery. Can’t wait to come back! Thanks again Sarah and Jonathan

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!

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!

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 absolutely loved staying here! The home is so cozy and had so many nice touches. Highly recommend, and will definitely be back!

Adorable apartment which was perfect for a girls weekend. Beds were super comfortable, everything was very clean, and all instructions were clear. Would love to stay again and enjoy the outdoor area!

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

Very nice place close to restaurants and coffee shops. Very clean and neat. Responsive host

Marks place was perfect for going to a concert at the KPAC. It is walking distance. There are also cute breweries shops and restaurants nearby. A great location and a great host!

Ann Marie’s place is a true gem! This was my first stay, and I already know it won’t be my last. The apartment was spotless, beautifully decorated, and stocked with everything I could possibly need—including a serious coffee setup (bless) and the sweetest wind down: a bottle of moscato and a charcuterie plate, which this tired teacher truly appreciated. Ann Marie’s hospitality goes above and beyond—she’s warm, thoughtful, and incredibly responsive. Every detail was so intentional, it made the entire stay feel personal and special. The location is perfect, close to everything in the Hudson Valley/Beacon area, but quiet enough to relax and recharge. I can’t recommend this place enough. Five stars don’t quite cover it—thank you so much, Ann Marie! I’ll absolutely be back!

We stayed here for our daughter's graduation at the Culinary Institute. It was a beautiful 30 min back and forth from the campus. There are great restaurants all around within a short drive. We couldn't have felt more at home. Peaceful location and fully stocked with anything you could possibly need for your stay. We highly recommend staying here for any trip near or around the Hudson Valley.

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!

Absolutely loved staying in this cozy place. It’s such a vibe, so comfy and cute. Dan was an excellent and responsive host, made it so easy. I whole heartedly recommend staying here, I definitely will again.

Could not recommend this place enough! Darla and Matthew are extremely communicative, sent lots of great recommendations, the house is very cozy and well-stocked, the neighborhood is walkable to lots of great shops and food, and the check in and check out process was a breeze! Would definitely stay again. An amazing value for the price.

This is a wonderful stay in a cozy private room. The hosts were incredibly kind and welcoming and made me feel right at home. The room itself was very comfortable and well-appointed. I was encouraged to use the shared spaces, such as the living room and kitchen, which added to the warm and inviting atmosphere. I’d recommend this listing if you’re looking for a friendly and comfortable stay.