Family-friendly holiday rentals in Round Top

We had a lovely long weekend with our 20 year old daughters and our dog. We celebrated a birthday and midsummer and really relaxed. The house was comfortable, clean and offered an relaxing environment. The Sauna, hot tub and She Shed were fan favorites with our family! Highly recommend for a family of 4-6.

We went for a quick weekend getaway with our two dogs and absolutely loved William and Liz’s home, we didn’t want to leave!! I loved the privacy, how peaceful it was, and of course the views! Our dogs enjoyed all the free space to run as well. We unfortunately had a lot of rain when we stayed, causing our tour of howes cavern to be canceled due to flash flooding. We were rescheduled which affected our check out time, but they were so sweet and offered us to check out whenever we liked and even offered us an extra night to stay! (We wish we could have). It was a wonderful weekend getaway and we all can’t wait to go back! :)

A quiet private property located close to amenities, the city of Hudson, and nature. It is a beautiful and comfortable home filled with creative and tangible care. We enjoyed cooking in the kitchen and spending time on the property over a long weekend stay.

We loved our stay. They provided everything you need plus more. So comfortable, lovely ambiance and the sauna and hot tub were fantastic. We came on a rainy day and still had a great time. Location is 10/10. Loved the calmbucha. Highly recommend!

Great place that was clean, comfortable and cozy. There were excellent instructions for everything and my family loved the hot tub!

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.

Dror’s place was the ideal getaway. It was just the right size for one or two people. It was clean, cozy, and had all the right amenities, including coffee makers, coffee, and even a frother! Unfortunately, it rained all weekend, so I couldn’t enjoy the hot tub. But the space in the backyard was very peaceful and inviting. I left you a drawing, Dror, and wanted you to know that I haven’t drawn in many years because of a busy life. Your home brought that out in me. Thanks again!

The Little Minka was everything that Daniel said it would be. A beautiful, peaceful, quiet, cozy home with an amazing minimalist aesthetic. Definitely a great place for a weekend getaway if you’re looking for a break from the hustle and bustle of the city. Would recommend and look forward to booking again!

Arin & Brian’s place was nothing short of amazing ! From the minute we walked in , it felt like home . Our 21 month old daughter especially took a liking to the home . I was so shocked and happy to see how baby/toddler friendly their home is . From child locks to stair gates , you name it , they had it all! It was also very peaceful surroundings and private, which I always appreciate in an air b n b. Arin and Brian were great hosts too , checking in when needed. I would love to come again !

Beautiful space. Amazing countryside vibes. Fun hike down to the waterfall, great kitchen for cooking and a fun night in. There was lots of quaint stuff to do in nearby Middleburgh: thrifting, diners, 50s milkshake bar, antique book stores, hikes, breweries, and more. We loved that there was so many towels for the sauna and swimming. One note: give yourself a lot of time for the sauna to heat up. Instructions were clear and they gave us lots of local recs. Also LOVED the hammocks -- lots of cozy nooks to hang for a chill girls weekend. We might be back again! A great stay.

We had a wonderful, no-phones weekend here with our dogs. Loved hanging on the porch and playing in the yard. Plus, an easy ten minute drive from ice cream! We will be back.

We loved our weekend at Brookside Barn! We were thrilled to find this pet-friendly availability for a last-minute getaway. Clean and cozy, peaceful inside and out, walking distance to the village, bookshelf and board games for rainy days (which we had), easy check-in/check-out process and clear instructions!

Easily one of the nicest little cabins around. Can’t beat the privacy / grounds with Mountain View’s. There are nicely landscaped walkways and paths all around. We also appreciated the convenience of firewood and drinks for purchase on the property. Great location for hiking, snowboarding, fishing, not far from breweries like west kill, and towns like Woodstock. Paul was a great host who was very responsive to any questions we had. Will definitely book again.

Had an absolutely wonderful stay at Lena’s place. Very quiet, very serene— but close enough to downtown Hudson for when I wanted a night out. The dogs absolutely loved our walks up the long scenic (and completely private) driveway. The cat adored birdwatching from the sliding doors. We will definitely be coming back!

By far the best Airbnb experience I've ever had! Joni was an amazing host, and I also had the pleasure of meeting her husband Rob/seeing their unique, beautiful home. She was responsive and very helpful throughout my stay, and even taught this "non tech savvy" person how to operate the TV! The location is perfect- and in my case even more so, as I attended a family wedding at the Colony just a block away! Its a 5 minute walk to town, and at the same time very peaceful/private- a perfect combination. I fell in love with Woodstock and wish I could have stayed longer. I'll definitely be back, as there is much more to explore in the area- will definitely stay at Logstock when I return!

I loved my stay. Perfect cozy cottage to escape the city. Extremely quiet and peaceful. The house had everything you need and plenty of beautiful hikes nearby. I would definitely come back

We had a magical weekend away and our stay was everything we hoped it would be, and more. Olia was incredibly responsive, friendly, and all around wonderful to connect with. The house was a magical time capsule holding the best of energy and a glimpse into the 70s - so fun. The pool and patio were awesome, with open and friendly spaces inside too, all made for the best of entertaining spaces. We could not have asked for a better weekend away, and we cannot wait to plan our next trip! Thank you!

This is our fifth year coming to the farm. Larissa is absolutely masterful with kids of all ages (even tough kids). My daughter races out at 9 am to do farm chores and begs for more (and this is a kid who drags her feet doing chores at home)!! We love the rhythm of farm and find it really easy to disconnect and unwind. After chores in the morning, you're welcome to spend as much time as you want with the animals, which is a real treat. Whether it's feeding the horses hay, sharing food scraps with the goats, or watching the chickens do their evening routine, there's so much to enjoy. The local towns are lovely, but if you like the farm experience, you may never leave the property. Larissa is incredibly knowledgeable and generous in sharing her experience and expertise. She has created an absolutely magical environment, and I would highly recommend visiting!!

We absolutely loved our stay ay Susan's place. We were celebrating our ten year wedding anniversary with our dogs and it could not have been more perfect! The private pool setting, access to the rail trail that leads directly into town, the giant windows bringing the outdoor greenery inside, the Frida Calla 500 piece puzzle, the I pad hooked up to a lovely sound system, I could go on and on. We rarely visit the same place twice, but we made need to break that streak with this place.

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!

Cozy home, on a beautiful property. The natural pool is really special, and we loved staying here. Hope to be back.

Beautiful country home, SUPERB location, large grounds with a beautiful pool, and communicative and kind host. We had a wonderful 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.***