Family-friendly vacation rentals in Highland Falls

Captain Dan's artists retreat is a one of a kind, beautiful space to unwind. We celebrated New Years here and had a truly special time. Highly recommend to all those looking to take a few days away from the hustle and bustle to reconnect with nature, art, & a hot tub!

Michael and Enrique were excellent hosts, and left me and my girlfriends ice cream in the freezer to enjoy! They responded quickly when we had any questions. The view from the hottub looking out onto the woods is beautiful and the hottub was just what we needed to relax. A beautiful, cozy getaway, and so close to Rhinebeck!

We had such a nice stay in Olivebridge. Wray’s home is beautifully decorated and extremely private, and just a half hour drive to Woodstock, where there are plenty of shops and restaurants to explore. The hot tub was a bonus, as was the very eclectic DVD collection. Highly recommend! Thanks again for having us!

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!

Evalina and John were the best hosts we’ve ever had! There was a big winter storm during our trip and the power in the area went out briefly and John was over at our place turning on the generator right away. Highly recommend staying here

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!

Perfect location — it’s directly in the middle of Minnewaska State Park and downtown New Paltz. Stargazing in the hot tub was a perfect way to relax after a long hike.

This was such a nice space and Lisa was a nice and accommodating host. This place is full character and wonder. Very artistic color energy in this place. We started my daughter’s 18th birthday celebration here with what is her last sleepover with friends. The hot tub, steam room and sauna were the first things and last things used. They enjoyed it so much! Thanks for your hospitality Lisa. If we ever need something like this again. We will be sure to look you up! Blessings

The Woods House was even better than the photos and description make it out to be. The location was perfect- close proximity (10-15 minutes) to nearby towns, but far enough away that it felt secluded and peaceful. There are tons of good restaurants in the area along with great hiking. The home itself was sparkling clean when we arrived and was super cozy. We particularly enjoyed the wood stove, the beautiful tile shower and the kitchen. The appliances and cookware were modern and clean, and the kitchen was stocked with any and all tools you would need to cook a meal. The loft bedroom was beautiful as well, with huge windows looking out to the forest. We received a significant snowfall on our third night at the house and it was a beautiful scene. Despite the large amount of snow, the driveway was plowed and the walkways were shoveled by early the following morning, which we were extremely grateful for! We enjoyed our winter getaway immensely and would recommend it to anyone!!

Peter's place is THE perfect stay for a couple (plus dog) planning a visit to Rockland County. The cottage is extremely clean and incredibly cozy. The surroundings are beautiful, with the property well set back from the road and bordering Harriman State Park. Suffern and its restaurants aren't far and there's easy access to the Palisades Parkway to go anywhere else nearby. I grew up in the county and visit my parents on a regular basis. Any time I can't stay at their home, Peter's place will be my go-to from now on.

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!

Where to begin...Joshua's Outlier Inn microcosmos is really the loveliest place and has such variety of things to see and do. About half of the compound is little cottages and bungalows that are fully winterized and with all modern conveniences, including wifi. We staid in the bungalow for 5 nights and loved it. The other half is a summer-only "glamping" setup with a variaty of geodesic domes, tiny homes and cabins, with shared outdoor kitchens and showers and with outhouses. Communal year round sauna and hot tub. The place has sheep, chickens and alpacas, a great little farm store with local products to eat, read or wear. Meticulous recycling and composting. Great hikes, eats and breweries are nearby. We had such a wonderful time and were able to come with three dogs, who loved every minute as well. There is no doubt that we will be coming back, and soon.

Mahmoud's accommodation was more than we could have wished for, it was perfect and had the most incredible views of the Hudson River and surrounding mountains. Mahmoud was very responsive and was able to answer all of our questions and fulfill our requests. We highly recommend his home to anyone else that's interested and we would love to make a trip back sometime in the future!

Erik's place is a Gem. It is located in a beautiful area close to New Paltz and Gardiner. The home was amazing, clean and well equipped. Erik and his father George were very responsive from the booking process, follow-up, directions to the place and took care of our requests promptly.

Three of my friends, and I were traveling to NY for the weekend. Even though this place is old, it has a lot of beds and plenty of space and amenities. We were comfortable and it was a great place to stay for our group or even larger. But the host, Brandon, made for the best experience. He had clear communication, and it was always accurate. I felt like he wanted us to have a good time and was supportive. I would definitely stay in one of Brandon’s units again. I highly recommend.

Really cute place. Comfortable beds and Sofas. The propane fire place was ideal. It was cold and icy when we stayed and we pretty much stayed in the whole time. It felt very warm and cozy. John was very responsive and helpful, he made the whole experience very easy for us.

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

Susan’s home is wonderful. The layout of the house was perfect. We had my elderly parents with us and we did not feel at all as if we were on top of each other. The kitchen was also perfect for a small group to entertain and was loaded with amenities! Everything was spotless and exceptionally clean. It’s very close of the village of New Paltz (3 min. car ride) where the restaurants and shopping is located. We also had a nice view of Mohonk Mountain! All in all it was a perfect and peaceful getaway weekend in the mountains!

I had a lovely stay at Sherrill and Clark's! I stayed for a month while working a job in the area, so I wasn't around much, but the space was a very cozy and homey place to come back to at the end of each day. Sherrill and Clark were very kind and welcoming. The bed was big and comfy! If you live in a city and need some time away New Paltz is adorable. Being from Chicago, it was a great change of pace.

We had an absolutely wonderful stay at Hava’s Airbnb! From the moment we booked, Hava was an incredible host—warm, welcoming, and unbelievably reachable. She responded to every question we had almost instantly, whether it was about check-in details or local recommendations, making the entire experience seamless and stress-free. The place itself was spotless, cozy, and exactly as described, with thoughtful touches that made us feel right at home. Hava’s communication stood out—she checked in to ensure everything was perfect without ever being intrusive. Her suggestions for nearby spots were spot-on, and it’s clear she genuinely cares about her guests’ comfort. We couldn’t have asked for a better host, and we’d love to stay here again. Highly recommend Hava to anyone looking for a fantastic Airbnb experience!

was a great stay loved the room.

We had a great stay and wonderful family time together. Once at the destination, there really was no need to leave if you bring everything, including groceries, that you want for the stay. It was amazing to get away and enjoy the quiet tranquility.

We had a wonderful stay at Diane’s. We were looking for a weekend away without the kids to recharge. We were able to do just that. We enjoyed the hot tub, and curling in front of the fire with a book. It was a snowy weekend but that just added to the charm. Diane’s scones are also amazing!! Diane made sure to communicate clearly and we were given all the info we needed to have a great time.

We had a peaceful and relaxing stay at Shawna’s beautiful Cold Spring country-style home. We were in town for a family gathering and accommodations, cleanliness and Shawn’s communication were five star. We absolutely recommend the house and Shawna as a host for you to stay with!