Family-friendly vacation rentals in Philipstown

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 only stayed at the Wandering Peacock for 1 night but it was such a treat as a place to crash along our road trip. Not a corner of the home was glossed over, every inch of the place is beautifully curated. Abigail was super responsive and a welcoming host. We squeezed in some time for the hot tub, it was ready to go in 2-3 hours and super relaxing. 10/10 would recommend.

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!

Peaceful surroundings, beautiful lake, wonderful house and amazing hosts! Had an absolute ball kayaking, fishing, and enjoying nature. This was my second trip and can’t wait to go back again.

This was our second stay with Joe and Amy hosting us and it was lovely yet again! They are extremely friendly and responsive. The place is serene and gorgeous. We absolutely adore the chickens and thoroughly enjoyed the fishing spot they told us about. It’s a beautiful place to unwind and relax away from city life. We plan to return again!

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.

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.***

Julie's place was the perfect winter getaway. The fireplace, hot tub and sauna warmed us and the very well-equipped kitchen enabled us to prepare great meals. The house was beautiful, with two living rooms for different activities and energy levels, a game room downstairs, a dining room with a large table and chairs, and comfortable furniture and beds throughout. Julie texted me to make sure that our every need was met. We had a snow and ice storm, and she had the driveway and walkways plowed, shoveled and sanded twice, and kept plenty of salt on-hand. We hope to return sometime in warmer weather so we can enjoy the pond, too.

Our family of 6 had a wonderful stay and we would go back in a heartbeat! The animals were a big hit with our kids, we loved feeing and petting them, such a cool experience for all of us! The play-set in the side yard was also so wonderful to have! The home was comfortable and felt super peaceful after a big day of travel! Jacquelyn was very quick to respond even before our stay when I was curious about a pack and play for our youngest and an extended check out time since we had a late night flight home! Sitting on the front porch with coffee, while the kids greeted the animals and the birds chirped was the best way to start everyday! The beds were cozy, the home was clean and spacious, such a perfect spot! Thanks for having us!

We loved our stay at this beautiful, charming, and peaceful barn. The space was cozy and thoughtfully designed—perfect for a relaxing staycation. The property itself is beautiful, and it’s just a short drive to great hikes, bike trails, restaurants, and breweries. A truly lovely spot to unwind and explore. Thank you for such a wonderful experience!

We were stunned by how magical this place was with all it's uniqueness of historic house. Spotless clean, spacious, very friendly owners. Our kids loved running around the back yard and playing board games that were provided. We would definitely come back, the only thing we regret is that we couldn't stay for longer, the area is very picturesque. many thanks!

A charming home, convenient to Woodstock and Phoenicia. We enjoyed the quiet, wooded setting (from inside you can hardly tell there are neighbors) and the cabin-like feel. Everything was very clean, Nickie's instructions to access the home were clear, and we very much appreciated that the place was dog friendly and that the main bedroom and the bathroom are on the main floor. The deck also has a gate, so had it not been so rainy, our dog could have hung out with us outside.

Bruce was very hospitable and his cabin was lovely. It was a very homey vibe , we had access to the lake, boats, grill and fire pit. There were bugs, but that’s obvious with being in the woods. We had a lovely stay at this cabin!

When you are accustom to five star and you just want a place to be absolutely quiet and be present with nature , this places is it !

Beautiful chalet with even better views - perfect for a calm and peaceful get away from the city, near hiking trails and 7 min from town for restaurants, had a great weekend and hope to be back soon

We had a great stay here as we explored nearby things (the Chuang Yen Monastery was delightful!) and visited some favorite spots. The weather was a little dreary when we were there, otherwise we would have made good use of the beautiful outdoor space. It was the perfect place for us to relax after our adventures every day—very quiet, very comfortable, clearly-written instructions for everything. We would be very happy to return!

My girlfriend and I had a great stay here. The place was cozy, well-equipped, and perfect for a relaxing getaway. The outdoor area was the true highlight — from the spacious patio to the beautifully maintained landscaping, the property felt peaceful and private. There’s also a pool that looked amazing, even though we couldn’t enjoy it due to the weather. We had some trouble during check-in after a delayed flight and arrived around midnight, but the property owners were just a phone call away and quickly helped us get settled, which we really appreciated. Overall, it was a great experience and we’d absolutely recommend this spot to anyone looking for a quiet, scenic place to unwind.

We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!

Perfect location right next to the mountain. You could tell Kristof put a lot of thought into the unit. Room was clean with all the amenities you need (and some more in case you forget). He was super responsive no matter what time of day. Check in / out was seamless and private parking in the hotel was vital. Will DEFINITELY stay here again if we come back to the mountain!!

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.

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.

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!

Amazing amazing for a birthday weekend. Good proximity to Hudson while still feeling in the woods. So clean and cozy.