Family-friendly vacation rentals in Round Top

This space is so lovely, the hot tub worked perfectly and provided many cozy nights outside. The plants are BEAUTIFULLY tender and bring a loving atmosphere to the space. the linen sheets were so wonderful at the end of the day. we made it up the hill in a Honda insight, but if it were a tiny bit icy I don't think we would have been able to make it. definitely use 4wd if you have it. the hosts were very responsive. if the noise is too much in the bedroom at night (critters, rain,etc.) be sure to use the fan they provide, it helped us a lot :) the kitchen was a delight to use. sharp knives. big, metal surfaces. nice gas stove. big fridge.

What a peaceful wonderful time we had in this cherry red cabin. Thank you for warm healing waters, sunny blue skies with mountain views, cozy sleeps and wonderful times cooking and gathering around the cozy cabin. We unplugged, biked the reservoir, ate lots of yummy veggie food, danced at the Bearsville Theater, and breathed in the magical mountain air. Thanks Woodstock and much gratitude to our host Mirav for creating a wonderful retreat. Blessings.

We had an amazing stay! The setting was absolutely beautiful, with stunning views and a peaceful atmosphere. The space was impeccably clean, which made our stay even more enjoyable. One of the highlights was the hot tub – it was the perfect way to unwind after a day of exploring. The host was incredibly responsive and saved us with a last-minute booking, which we are so grateful for. We couldn’t have asked for a better experience. Highly recommend!

Michael and Enrique were excellent hosts, and left me and my girlfriends ice cream in the freezer to enjoy! They responded quickly when we had any questions. The view from the hottub looking out onto the woods is beautiful and the hottub was just what we needed to relax. A beautiful, cozy getaway, and so close to Rhinebeck!

Very secluded and cozy - the perfect spot to unwind. Can’t wait to go back!

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

I had a great time at Tracy’s place. The house was really new (much better than the photos). Location was amazing!

My wife and I had a wonderful stay at this cozy cottage in upstate New York. The space was spacious and well-maintained, with multiple floors that offered plenty of room to relax. Everything was spotless, and we especially loved the hot tub and fire pit —it was the perfect way to unwind after a day of exploring. The cottage truly felt like a home away from home. I highly recommend it for anyone looking for a peaceful getaway!

What an absolutely fantastic property! The home was perfect for our party of eight adults for a 50th birthday. Woodstock is the most adorable town with tons of fun things to do. You must get the stuffed bagels from moonrise. We couldn’t have expected a better experience with the house, the amenities, and The kitchen was very well appointed. I would absolutely come back here again and probably will.

I booked Nidhi's place for one night for myself and a guest to attend a show at Bearsville. The placement of everything, inside and outside, created an intentional sense of comfort. My guest arrived after me - without a thought, we ended up at the kitchen table talking for hours before the show. Again, the placement of this conversation spot felt intentional, but only after we found ourselves engaged in it. The outdoor surroundings are utilized to not only accent, but to enhance the indoor setting. The whole experience felt private and safe, and allowed us to share a really precious window of time for reconnection and decompression. In addition to the appealing aesthetics (the chosen blue for that kitchen!), the bedding was a treat to come back to at the end of the night - so inviting and equally comforting to find yourself wrapped up in in the morning. Nidhi so kindly messaged me out of concern for the very high winds we were experiencing (prepared with a generator), but no issue.

Lovely place in Saugerties, close to lots of great hiking and restaurants.

Scott's place was great. We were so relaxed and felt right at home. We will be going back which is the best compliment I can give an AirBnB. The views were beautiful!

I loved staying in this home and hope to rent it again. It is just a few minutes from town and nestled in the woods. The place is beautifully decorated and has everything you need.

Their place was super cute and clean. The type of style and decor is to die for ❤️ Had all the towels we needed. Loved getting in the hot tub in the winter. Just wish there were blinds that weren’t totally see through! Also, we barely went into the “great room” because that room is a lot colder than everywhere else and we couldn’t figure out how to use the pellet stove in there without it smoking like crazy. Loved the place nonetheless. It was great for a birthday celebration with friends!

I enjoyed my stay at Gavin and Alison's house in the Catskills. It was a great place to spend a snowy winter weekend in January with my son and two grandchildren. The house is a short drive from various skiing and winter-sports resorts. We were satisfied with the kitchen and other amenities, played board games, and generally had a relaxing time. The hosts were very responsive when we had questions.

We spent a wonderful holiday weekend at Niall’s home. It was completely charming and very cozy and location was near Windham which was perfect for us. Niall was a terrific communicator, quick to respond to any question I had and very accommodating. We will definitely be back.

My group loved our stay at Alan and Cara’s place for the Sheep & Wool festival. Great space for a large group; we especially loved how comfortable the living room couches were and how there was space for everyone there to gather. The place was immaculately clean. We’d love to come back again!

We had an amazing stay at Tina’s Airbnb! The house was beautiful, peaceful, and perfect for a relaxing getaway. Tina was incredibly accommodating, allowing us to check in early and stay longer. We loved the large windows, high ceilings, and especially the glass door that opened to fresh air. My wife particularly enjoyed the bathtub. We had a wonderful, restful time and will definitely be visiting again!”

Loved the house. Kitchen is great. Awesome living room with very comfortable couch and fireplace. Bedrooms perfect. Hot tub was perfect. Original Nintendo system upstairs was fun. Went skiing at Hunter which is 20-25 min away. Woodstock 15 min away. Really a great place. Jaime was responsive, friendly and helpful.

We had a terrific stay. The house was exactly as advertised.

This was the perfect place for a weekend away from the city with a few couples. The hosts were so communicative and hospitable from the moment we arrived, ensuring we had what we needed (including sharing some amazing farm fresh eggs!). Our group loves to cook and the kitchen is an amazing space for friends to cook and hang out. We even had some fun using the pool table. The bedrooms were all perfectly comfortable and the bathrooms notably had great water pressure. Our dog also loved getting to run around outside in nature on the property. Location was very close to Rhinebeck where you’ll find tons of cute local stores and restaurants. We are already discussing coming back with friends this summer!

We spent three nights at Rich and Sheila's place and it was an amazing getaway. Our apartment was perfect-clean and comfy. We loved the proximity to the creek and the pool was a huge bonus! Rich and Sheila were both responsive and welcoming. We look forward to a return trip.

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 👍🏼

Amazing location with a gorgeous yard! The house was fully stocked, making it a breeze to cook for our guests. Joseph was incredibly communicative and immediately took care of a minor issue in the basement. We had such a peaceful, bucolic stay—perfect for runners with lots of hills to explore. And the pool toys added so much fun to our weekend! Highly recommend!