Family-friendly holiday rentals in Round Top

Great place! We had a weekend of hiking planned, but with all the rain, we were glad to have use of all the inside amenities here! Sauna, bbq hut, she-shed, basement game room and comfy living room all left us fully entertained while it poured outside. Would love to come back someday!

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! :)

Ami’s place was great! Stayed for my birthday and was surprised with a delicious tres leche cake upon my arrival! The view was incredible, amenities were amazing, overall it was everything I hoped for and more. Thanks Ami!

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.

The place was amazing and featured everything we were looking for. Tammy and Ed were super hosts and made the stay extremely enjoyable. We would stay here 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!

Jonathan’s place was fantastic! Location felt like a secluded oasis, but was only 5 mins to town. Everything was clean, hot tub and sauna included. Our pups greatly appreciated running around in the fenced in yard. Jonathan was quick to respond the one time we messaged. Would absolutely stay there again!

We had an amazing stay at the Georgie cottage! Andrew provided lots of great recommendations for restaurants and things to do in the area and the cottage was cute and peaceful. The kitchen was well stocked and the cottage was well-insulated and surprisingly cozy at night! We would love to stay here 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 !

This is my second time staying at Susan's place. Susan is such a warm and welcoming host. I feel so comfortable when I stay there. She is not only a gracious host to us humans but she is also a fur baby mama too and allows you to bring your fur baby with you. My boy Dunkin enjoyed his second time here again. Susan's place feels like Home. She gives a lot of local recommendations and a variety of things that you could do depending on what you like. You have a parking space and you can walk into town very easily. It's so peaceful where you stay and when you walk later in the evening you can see the deer grazing. It's just such a beautiful sight and I'm grateful for Susan and her place so that way myself and my fur baby have a peaceful and safe place to go to enjoy a nice few days of relaxation. I will continue to come here as I feel it's a home away from home.

Great location for our weekend getaway, close to shops, supermarket, restaurants. Lisa went above and beyond filling mini fridge with drinks, breakfast supplies, fresh fruit and snacks. Couch in the living room is comfy to sleep on for a couple of days. If you are light sensitive, bring an eye mask. Space is pretty bright in the morning due to small window on the ceiling above the bed.

The perfect spot to be nurtured by nature! The sweetest cabin had everything we could need and gave us the ability to unplug, relax and rejuvenate. Loved being able to go hiking and just enjoy being outside.. surrounded by gorgeous nature. The babbling brook was so soothing. Honestly, just a perfect spot to enJOY!

When I first pulled up to Kliment's, I literally teared up - that's how breath-taking his spot is. It was just what the doctor ordered... if doctors actually treated your mind, body, and soul and not just your body :) Seriously though, Kliment's place was an oasis for me: private, quiet, peaceful, with amazing views of the Catskill mountains. His home itself was beautifully decorated, simple yet super cozy, and had everything I needed and then some. (And the chickens were lovely company as well!) Kliment is one of the best Airbnb hosts I have ever had, hands down. With a very hectic schedule, Kliment was flexible, responsive, kind and patient with accommodating my many change requests and needs throughout my stay. Kliment is not just a wonderful host, but also a truly wonderful person - the world needs more people like him. In short: I can't recommend Kliment's home or him as a host enough! If you are hovering over the "Reserve Now" button, book it!!! You won't regret it! :)

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!

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!

Cute house, open concept first floor was great for a weekend with our girlfriends! Hava was very responsive and kind!

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!!

The house met all expectations everything is stylishly done, and the host is incredibly responsive and helpful 🤍

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.

Our second time staying at Maitopia with our cat, just as wonderful in a different warmer season. Tina was super responsive as usual and even accommodated a late checkout. We enjoyed feasting in the kitchen as well as grilling in the yard, floating around in the pool when it was warm enough out, "hiking" with our cat on a leash around the forest on the property, taking baths, streaming music. We didn't leave the property much, but it was a fun highlight to get a few local produce items at nearby Greig farm and meet the adorable goats. One tip- bring an eyemask if you're sensitive to light in the mornings- there aren't any window shades in the bedroom.

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.***