Family-friendly vacation rentals in New Windsor

We had a wonderful time at this place for our mini moon. It was relaxing, beautifully decorated, well stocked with everything you need! The hosts were very responsive. We would stay here again in a heartbeat! For anyone coming from NYC we stoped at Pho Tibet in New Paltz for lunch on the way home and the food was amazing!

My family of 8 adults needed a place to stay near a wedding at Glynwood. This wonderful spot was minutes away from the farm and town. The number of bedrooms and bathrooms gave everyone the privacy desired while the well equipped kitchen and living rooms had plenty of space for gathering. The house and land are beautiful, including the trail. Paula was easy to communicate with and my whole family felt comfortable and happy with the spot. Highly recommend!

Abagail was very helpful in getting settled. The house is full of interesting antiques and paintings. There was a wonderful view of the Litchfield Hills and a lot to do outside. It is rustic but it has every convenience of home. Great shower. Must have been a barn but now it is a museum of Art Nueveau treasures and stained glass. Very peaceful and slept great.

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.

Surprised my girlfriend with a weekend get away for her birthday and she was thrilled. Evelina and John are great host and their place is warm and welcoming. We loved the lake, and the quiet serenity of the location is perfect for a weekend trip from the city. Also loved the kitchen which made cooking in a breeze because how thoughtfully organized it was. Although our stay was short we did find time to take the canoes out explore the lake and take a refreshing dip. Our only complaint was that our stay wasn’t longer, and we’re both looking forward to coming back !

Great location on the lake. House has all you need. Boat dock, several decks and chairs, ping pong table, kayaks and option power boat rental. Only issue for perhaps the elderly and handicapped would be the amount of stairs required for entry and lake access.

The Barnhouse was very beautiful and cozy! Comfortably sleeps 8 with enough bathrooms for all to share. We especially loved all the plants and how easy it was to entertain a group of 8. The only qualms we had were the shower in the master bedroom and that there were quite a few lights out around the house which was especially challenging in the kitchen.

We had such a great stay at Eugene’s place! The house was perfect for our group — spacious, comfortable, and full of fun things to do. We especially loved the private theatre, the hot tub, and especially the sauna — such a great touch! The volleyball net was a hit, and there were tons of games in the closet that kept us entertained. The kitchen was well-stocked and roomy enough for us to cook meals for our large group, and there were plenty of different areas to hang out in, everyone could find their own space to relax. The towels were plentiful (huge plus) and having access to the washer and dryer came in handy during our stay. Eugene was a fantastic host — super friendly, very responsive, and just really helpful all around. We also got to enjoy a few deer sightings right in the yard, which felt magical. We visited the nearby alpaca farm and did the Beer Mountain hike, which was a nice outing. All in all, a wonderful stay. Would absolutely come back. Thank you Eugene!

Jacquelyn was very responsive, proactive, provided clear instructions and her place and linens were very clean! If you love farm animals, you’ll enjoy this place even more as she allows you to visit her farm.

Jonathan and Amy were the perfect hosts. Super friendly and resourcesful. The property is beautiful and so peaceful which was perfect for our down time as we were in town for a three-day wedding. We enjoyed breakfast with the family of deer that live in the back field and so many beautiful birds. The apartment is so quaint, very clean and has everything that we needed. The beds were super comfortable. It was decorated to the age of the property which we loved! It was a great find and we highly recommend the apartment and will surely book again if ever in the area.

We had a really lovely stay at this cabin in Boiceville. It rained every day during our trip, but honestly, we didn’t mind—it made the space feel extra cozy. We spent our time relaxing indoors, reading, cooking, and just enjoying the slower pace. The cabin was clean, comfortable, and had everything we needed. It was tucked away enough to feel peaceful, but still a short drive to Esopus Creek and Phoenicia, which we enjoyed exploring when the rain let up. The host was helpful and easy to communicate with, and everything about the stay went smoothly. If you’re looking for a calm, quiet retreat in the Catskills—even on rainy days—this spot is a great pick.

Would absolutely stay again! Really loved the way they've updated the space but kept the classic touches of the house. Huge well appointed kitchen with everything you could need. Peaceful outdoor space with lots of privacy. And overall a very spacious house that feels like you could have a big group without getting in each others way. Ryan & Lauren were super on it. Will definitely recommend to friends.

Very nice house, good fishing and wildlife nearby. A little closer to the neighbors than expected, but overall a great place and would love to come back

This place is truly a gem! We enjoyed swimming in the waterfalls and relaxing under the trees. We can’t wait to return. The house is also lovely with lots of interesting and quirky touches that we enjoyed. Incredibly well stocked kitchen and everything we could want!

Dan's place was lovely. Lots of light, beautiful views of the Hudson River and dog friendly. Dan himself was responsive, flexible and helpful. I don't think I'll stay anywhere else when visiting family.

We had such a great time that we ended up booking another stay on our very first day! We came for Father’s Day weekend and were really impressed by how many thoughtful touches and recommendations were listed in the guest handbook. The dog beach was a huge hit with our puppy, and we had a blast. Thanks for helping make our vacation so special!

Everything was exactly as was stated and it met the expectations and more. Would recommend anyone to stay and if I ever return will definitely rebook.

This A-frame escape was exactly what I needed — the perfect break from the city. The place is beautifully designed, cozy, and filled with thoughtful touches. The jacuzzi was absolutely incredible, especially under the stars at night, and the A-frame structure made the whole stay feel like a peaceful retreat.

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!

We had an amazing stay at the cottage! It's modern and thoughtfully designed, but still feels cozy and inviting. It’s tucked away in a peaceful spot surrounded by trees, yet only a 3-minute drive from town. You feel totally removed and relaxed, but everything you need is right nearby. I worked remotely for part of the trip, and the setup was perfect. There’s a dedicated desk with a view of the mountains, and the Wi-Fi was fast and reliable. Natural light poured into the cottage through the skylights. It was spotless and comfortable. The bed and linens were top notch, water pressure was great and hot—little details that make a difference. The pool was a highlight. It’s heated, with plenty of loungers and umbrellas, and it felt totally private and calm. We ended up spending an entire day out there just soaking it in. The hosts were lovely. They were helpful when we needed them, but also gave us complete privacy. We’d absolutely come back and highly recommend this place to anyone!

We truly enjoyed our stay at Wilderkill Barn. Maria Cristina and William were exceptional hosts—warm, attentive, and genuinely committed to making our visit special. They went above and beyond to make us feel welcome. The home was a haven, with a hot tub, sauna, pool, fire pit, pool table, and immersive sound and movie systems—all of which made our stay delightful despite the cold, dreary May weather. We can't thank them enough. ***That said, we feel it's necessary to address a serious issue with Airbnb itself that arose while booking this property, unrelated to the property itself. An unexpected tax was added after booking, and Airbnb has yet to provide a clear explanation. After years of loyalty, we were disappointed by their evasive and unhelpful customer support. This experience has made us reconsider using the platform in the future. We urge potential users to scrutinize all fees carefully and be aware that Airbnb’s support may be difficult to navigate if problems arise.***

Three friends met at this beautiful carriage house with the feel of a French chalet! We stayed two nights with varied weather conditions. The house, grounds and location was perfect. Hot tub was used and so relaxing. The surroundings were beautiful and peaceful. The host, Diane was very helpful and friendly. What host makes scones each morning and delivers them warm?! Visited the Ashokan Reservoir trail, Opus 40, and Woodstock. Recommend this home highly. You won’t be disappointed!

We had a beautiful stay in Kerhonkson for a relaxing bachelorette weekend! Lillian’s place is absolutely beautiful and was so comfortable for my friends and I. Everything was as described, extremely clean, plenty of linens and had everything we needed in the kitchen to cook a few meals. We enjoyed sitting by the pool when it was sunny. Lillian was very communicative and flexible with check in time. Thank you!

It was comfortable, very roomy, and cozy. There was good shared space and good privacy. The grounds were lovely, there was a great pool, and it was very convenient to so many good things to do in the area. It's one of our favorite rentals to date!