Family-friendly holiday rentals in Dutchess County

Loved this house! We have stayed in many places all over the world for both business and pleasure. This was a business trip. House was great, location was great. It was cold and rainy so we didn’t get to enjoy the porch, deck or hot tub . Even without these amenities we totally enjoyed the house. Hoping to stay again next time we are in the area. We are in Rhinebeck twice a year for the antiques show in the Fairgrounds . Instructions on house were easy to understand and concise. Great job guys!

Billy and Rhobin were so helpful and easy to communicate with. The house was so comfortable and peaceful. The property was lovely! 5 Stars all around! Thank you for a fantastic stay!

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.

What a gorgeous stay. My partner and I celebrated our five year anniversary here and each detail was perfect. The home is wonderfully curated, with stunning art, decor, puzzles, plates, you name it! And by the window, the feeders attract all kinds of birds that I’ve never seen so up close. Woodpeckers, cardinals, chickadees. You hardly need the TV, it’s so entertaining. The place is spotless and serene. And Rosy is so responsive while giving you complete privacy! You can tell she really cares about the experience she provides. If you’re looking to stay in an artfully cozy home, this is the place.

We had such a lovely time staying at Scott’s house recently. The house is wonderful and you can tell the owners have really put a lot of care into making it special. The amenities are awesome - the hot tub, sauna and steam shower were so relaxing, and there were also lots of things like games, toys, etc that were perfect for kids. We also really appreciated how thoughtful all of the recommendations were for places to shop and things to do in the area, and Scott was super responsive. All in all, a perfect retreat to get away from the city and enjoy all the Catskill area has to offer. We definitely hope to visit again soon!

We keep coming back to stay here because the house is so cool and has everything you could need! A great getaway outside of nyc anytime and we always recommend to others.

Just what we needed for a relaxing weekend. Place was clean and comfortable. Situated in the woods- scenic, quiet and relaxing with the sound of the creek down below. Rainy weekend but it was dreamy looking out the large floor to ceiling windows. Highly recommend this place if youre looking for a quiet getaway. Rhinebeck Village and Red Hook shops are within 20-30 min drive.

Dana was beyond amazing!!! Super helpful and super nice! Went for a weekend getaway with my husband. The house was so fun we ended up staying there all weekend making s’mores at the fire pit and going in the hot tub! Definitely would want to stay there again !

My wife and I had a great time. Amazing house right outside of town. Huge yard which our dog loved! Hopefully we will be back.

Tim! Our stay was Beyond my expectations! Many many thanks, appreciation and affection. Be well~ Jen, Lucia and Jack

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!

Location was great and close to town. The home was very clean and fully stocked. Annemarie was very responsive and accommodating. Great stay!

This was a 12/10 experience! My girlfriend and I both brought out two pups and loved every second of our stay. Every corner we turned was a new decoration in the house that caught our eye, so creative and fun!! Soaked up the back yard, fire pit, and water! We will definitely be returning!!

This place is tiny and wondrous! So well-thought out and decorated, it is comfy and tasteful, clean and beautiful. The large trees and bubbling creek were magical and I walked through the town many times a day to get coffee or dinner or to look at the history of the area just blocks away. It is a partially below ground space with two windows. It stays cool and has fans if needed. You can hear the tenants upstairs as it is a shared house which was fine by me. It is rural ish so you hear the birds constantly and see the trees swaying but also bugs live in the country, so they coexist with you. It is a dreamy place at the edge of town.

This is a lovely stay nestled in the heart of Dutchess County. It is a short drive to Millbrook and not too far to Poughkeepsie and other surrounding towns. The home was clean and well kept. It has all the items you may need. The yard and spacious and surrounded by mature nature on a quiet road. An alpaca farm is just up the road and Zoe's Ice Cream Barn is around the corner. We would surely stay here again.

Skye was really helpful and always responded quickly. This is a private location but if you're looking for stuff to do, Carmel is a short drive to Beacon and Cold Spring. It is very pretty in this area and very woodsy. The space is in the lower level and cool and opens to a private yard with seating.

This beautiful property has a special place in our hearts. We stayed in the A frame during COVID and we always wanted to come back. This time we stayed in the main house and it was phenomenal. Wish the weather was better for us to use the pool, but next time! It well worth the price. Only an hr from the city and it feels like a full vacation. Wonderful way to lose time time for a few days. We will be back!

Debora’s house was perfect for a weekend trip out of the city. There was plenty of room for our group, and we had a great time in the pool and in the backyard. The kitchen and grill were easy to use and it was great having a full dining table and multiple indoor spaces to hang out in.

Ileana was great with getting back to questions we had and making sure that we were able to get into the place seamlessly. It was the perfect weekend get away.

Kathleens place was perfect for our friends and family weekend vacation upstate. The house and property was absolutely stunning and fit our group of 10 so comfortably. We were talking about our next stay there before we even left. Highly recommend!

My family had a great stay at Veronika’s home. It was comfortable, spacious, and conveniently located. The home had everything we needed, including essentials for our toddler. Veronika was easy to communicate with and responded promptly.

Absolutely stunning home, even better than the pictures. Feels like a place that is truly cared about. Furnished beautifully. The yard was also much bigger than we expected and beautifully kept. Pool was beautiful. Surroundings were all lovely rolling hills and farm country. Fully fenced yard was nice with the dog. There is a fence also separating the pool from the rest of the yard which is nice if you have young kids. A very relaxing stay. Keep in mind: no AC and no microwave. In May, we were able to cool the home off by the windows at night but it could be a little toasty in the evenings.

The most beautiful home and view. The most gracious host. We couldn’t have asked for more!