Family-friendly vacation 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!

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.

Gorgeous house, super clean and tidy inside, with comfy and modern furniture. The hot tub was fantastic, make sure you turn off the lights so you can see the stars! The only other heads up I’ll give is that the way to get in is through the back entrance! We tried the front door for like 5 minutes until the electronic lock blocked us from continuing haha. Great location to get away from the city for a weekend and go hiking. Lots of great trails really close by.

What a hidden gem. Cozy, clean cabin feel with enough privacy from other houses. Great amenities like a hot tub, fireplace, walkable backyard, comfy outdoor seating, nice mountain views, ample toiletries, and 2.5 convenient bathrooms. The hosts laid out everything we needed to know clearly and it was such an enjoyable, stress free vacation. We also enjoyed Roscoe's diner and the convenient Tesla charger. Overall an excellent house to stay in with everything you would need. The cats enjoyed their stay as well. 😺

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!

We enjoyed our stay at Caitlin’s cabin! Communication was great. The place was spotless. I loved the many plants inside and the peaceful surrounding area filled with many deers visiting the yard. Soaking in the hot tub was so relaxing at night. And the fire pit outside was a really nice touch to our stay. I recommend this cabin and host! We didn’t get to enjoy the kayaks because of the weather, but it’s really nice that it was an option! Thank you!!

Funky little artistic apartment was perfect for our graduation festivities.

We enjoyed the lovely cozy, private cottage with our family. It was a pleasure to have the animals nearby for the kids to interact with, a safe environment to roam in the woods, and very convenient to have the farm shop a few steps away for local eggs, meats, etc. The cottage was stylishly modern with a clean aesthetic and modern conveniences. Josh was very accessible via text/phone and checked in with us during our stay. We enjoyed ourselves thoroughly and would recommend to nature lovers, families, and those looking for a getaway in the woods!

Another great stay at Alex’s place, we’ll stay again if we’re back in the area!

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.

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.

My boyfriend and our 2 pups enjoyed our time here! The place was mostly stocked with what we needed (no lighter for fire pit or coffee filters that we could find (but it rained and k-cups were provided), which neither are a big deal, but things we didn’t think to pack - so pack those if you’d need them!), it was clean, and we enjoyed the location for hiking / fishing and good food! We’d stay here again!

We had an amazing time! Danielle and Ely were very accommodating and went out of their way to make our stay special. They answered all our questions, helped us book a table at Matilda, and even surprised us with complimentary wine. It was so thoughtful!

Karina’s place was perfect for our family getaway. The spacious home comfortably fit all five of us, and the kids especially loved the large backyard with a creek. The neighborhood was peaceful, with quiet neighbors, and we enjoyed easy access to nearby hiking trails and stunning natural surroundings.

A super stylish, immaculate and serene cottage with spectacular mountain views. This absolute gem is perfect for relaxing, decompressing and exploring the Catskills. The beds and bedding are super comfortable, kitchen is well stocked, and the sight line to mountains is a visual feast. The windows are plentiful for gentle, fresh breezes wafting throughout the home yet A/C and heat work well when needed. We built a fire and star gazed surrounded by a field of fireflies. The hum of bees in the morning sun while having coffee on the deck is a delight. There’s a thorough and helpful guide/manual and the hosts are extremely responsive. Be sure to spin some records - we found the Donna Summer Greatest Hits double album - plenty of room for dancing around. Will most certainly be back!

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

Kristof was an excellent communicator & his instructions were clear. He was responsive to my questions and the unit was as described. This location is very convenient for us to visit with family in the area

Paul’s condo was PERFECT for our family of 4. The condo is in pristine condition. Highlights include beautiful balcony over the view with a surrounding view, HUGE bathroom and very comfortable king bed. The amenities also made the stay tip-notch, including very large pool, hot tub, outdoor play areas and pool/games downstairs. The building was well-kept as a resort. Highly recommend: 10/10!

We recently stayed at Tina's and had a great time. The location is secluded, incredibly peaceful and quiet — all you can hear are the birds in the morning. The home itself is clean and looks just like the photos. We also loved that we could bring our dog along with us. We live in the city so our pup doesn't get to touch much grass, and he had a blast running through the fenced-in yard. Although we originally booked because the house has a pool and we were hoping for good weather, it rained almost the entire time we were there... Nonetheless, it felt like the coziest home for a rainy weekend, and we really enjoyed our stay. We loved sitting inside by the fire to watch a movie, cooking in the kitchen and building a fire outside when the rain stopped. The location was also great for driving into Rhinebeck, Red Hook, Hudson and surrounding breweries and wineries.

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 👍🏼

This accommodation deserves 5 stars, firstly because of Lilian’s communication: she provided local recommendations, was very responsive and checked in during our stay to ensure everything was fine. The amenities itself are also great, the pool and outdoors are very nice. Unfortunately we did not have good weather but the house itself has a stove, TV with all digital apps, toys for the kids etc so we could easily enjoy ourselves inside too. The kitchen has all the tools you need to cook so we felt at home. The check in and check out was contactless which made it very easy for us to come and go at our preferred times. The house is very spacious because of the open floor plan, the second floor is a vide which ensures that there is a lot of light and the ceiling is super high. Would definitely recommend this others!