Family-friendly holiday rentals in Monticello

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!

We had a great time fishing and going to local farms! The hosts were great! They even got us some night crawlers and helped find a hat we left & ship it back!

This was a nice AirBnB for the area, cozy and felt somewhat secluded despite being viewable from the main road. Perfect for a small dog to roam around on the grassy area, and the hot tub looking out into the back was a nice touch and enjoyable to sit in. We were looking for a relatively short get away from the city, quiet and close enough to things in the area to enjoy, and this fit the bill perfectly. The house was very clean with very clear instructions, and nice touches that made it feel cozy. Highly recommend for 2-4 people, particularly with small dogs.

beautiful place, friendly owners, everything you need to disconnect from a crazy world

We had a nice time staying. It has a Well stocked kitchen. It is near to grocery and shopping in Stone Ridge. It has Great fireflies at night and a good view of the sunset.

Beautiful inside and out — a peaceful oasis & retreat from everything! Nearby restaurants and hikes but also so quiet and private. Great weekend we will be back!!

The house is spacious and elegant. The wooded lot has a pretty creek a little way from the house. We took some walks through the snowy woods and roads beyond the house and could have kept going for a long time - the mountain is peaceful and beautiful. The owners live a few doors down and came by to help set us up before a major snow storm. We had a really nice time.

Great few days out of the city. It feels like the middle of nowhere but it’s 5 minutes away from center of Jeffersonvile’s main streets. Clean, spacious cabin was way larger than expected. Hot tub was private and great to unwind. Stephen was a great host who couldn’t have been more accommodating. Will book again!

It’s a really sweet location on a working organic farm. The stairs to get to the loft are definitely for the agile, but otherwise it’s a nice little lay-out.

This place is an absolute gem. From the moment I arrived, I felt a deep sense of peace—it’s incredibly tranquil, surrounded by beautiful natural scenery, with a running stream just steps from the front door. The home itself strikes the perfect balance between rustic charm and modern comfort. Inside, the decor is thoughtful and unique: a nostalgic mix of vintage childhood sports photos, striking modern art, and beautiful antiques. It all blends together to create a space that feels both stylish and deeply personal. The fireplace is a centerpiece—warm, inviting, and stocked with enough firewood to last all summer. This isn’t just a house—it’s a welcoming home. You can feel the care and intention behind every detail. Located just 15 minutes from Bethel Woods, it’s the ideal escape from NYC. I can’t wait to return.

We had the best time staying at this cozy cottage, very comfortable with an awesome view! Kitchen had everything we would need. Great hospitality from Wayne and Renee! We can’t wait to come back again soon

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.

Jane’s Old Schoolhouse is awesome. Whimsical, relaxed, well equipped kitchen, loved all the little knooks to curl up with a book & cup of coffee or wine. Would love to enjoy the porches, however both visits offered us rain & cool weather. Great for doing puzzles & enjoying the wood stove.

Great place to stay after seeing a show at Bethel Woods. Easy to find and less than 15min drive to catch the show. Erik was easy to work with as well. We will def book his place again when we come back for another show!

The cabin is beautiful and the perfect place to disconnect any time of year! It truly feels like a home away from home. We did run into a water issue during our stay, but Danielle took quick and thoughtful steps to resolve it and offered a very customer-centered solution. That really showed us how much she cares about her guests and takes her hosting responsibilities seriously. We had a wonderful time and definitely plan to be back soon!

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!

We loved this place and would recommend to everyone! Jennifer and Jose were so kind and communicative and so helpful! It was such a beautiful place and we would definitely book again! Thank you for everything!!!

We had a wonderful stay at this house. It was clean, spacious, very warm despite the cold, and had a terrific pool table and air hockey table. Our family relaxed and spent good time together.

This is a beautiful place. Second time we’ve stayed there and I would like to come again next year!

Paul's place was just as described. My husband and I had difficulty figuring out the thermostat and he was quick to reply to our request for help. The pool and hot tub were great! Very comfortable bed.

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 loved this cute studio cabin at the end of a quiet lane in the woods. The host was accommodating and left a welcome basket with tea & muffins for our arrival. The whole unit was clean and well maintained with basic equipment for cooking. We enjoyed sitting on the veranda watching the wildlife. Convenient location for Woodstock for coffee and food, & Ashokan reservoir for walking and cycling. There were a few potholes on the access road to the property which deer use to drink from (☺️). We loved that the cabin was bug free and did not have any trace of bug spray! (We get very bad reactions to that stuff). Thank you for hosting & being respive. Recommend for a weekend 👍🏼