Family-friendly holiday rentals in Windham

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! :)

Absolutely amazing place and experience. Everything about the place was great and the communication and service was the best. We received 5 inches of snow on our last night and they even had the driveway all plowed for us first thing in the morning. That was a very pleasant surprise. Highly recommend!!

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!

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

Actually, the photos of this place do not do it justice at all. This property is incredible! It was everything (and more!) of what we were looking for. A long holiday weekend very well spent in a clean, extremely well kept, and cozy place hidden in a beautiful forest. The hosts were top-notch! Incredibly helpful and super responsive. We would love to visit again!

Raymond was very thorough with instructions. Love the flowing creek and array of places to comfortably sit outdoors. Brought us wine to enjoy. Kitchen full of amenities. Living room was cozy as well as the beds. 2 bathrooms were nice and clean. Drivable locations.

Porter & Sara run an amazing cabin. Their container cabins are well equipped for a fun, romantic stay. The layout of the cabin lends itself to a warm welcome and the positioning of the couch, bed, and table make perfect use of the landscape - all facing the beautiful pristine meadow that hosts a ton of wonderful sights including deer, flowers and interesting insects! One thing that stood out was the lack of mosquitoes. Given the clearing and the amount of other wildlife, we were pleasantly surprised how comfortable it was to stay outside and not worry about being eaten alive. There are plenty of lounging accommodations, from nicely kept hammocks, to comfortable lounging chairs to a lovely hot tub . The low lights outside make the hot tub and patio a fun place to hang all night. When getting into bed, you’re greeted by the beautiful stary night. It was amazing to lay down and feel like we were all alone in the woods. We will absolutely be coming back for another romantic adventure.

Great home right on the neversink river! Really enjoyed our stay Father’s Day weekend and appreciated the clear instructions and how clean the hot tub was! Appreciate it!

The perfect place for a Catskills getaway. Raymond and Maura's house is peacefully secluded in the woods while being just a few minute drive to downtown Woodstock. The screened in porch is the perfect place to enjoy your morning coffee and take in the beautiful setting. We have stayed here several times now and hope to come back again soon!

Ivan's home was beautiful. The location on the lake was so quiet and peaceful. It was clean and it had everything we needed. We look forward to coming back again!

What a gem. Tucked away in woods, this house was just what we needed. Tranquil, gorgeous, homey, and a perfect reset. My dog loved exploring the grounds, while I admired the beautiful mountain view. It was a little chillier than expected when we arrived but host sent directions for food recs and suggested we take advantage of the fireplace, which we did. Everything was very easy to find in the kitchen and bathroom, and my bedroom was cozy. Loved it very much, and would stay 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.

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!

What a great place for weekend of relaxation. Although it rained most of the weekend, we made great use of the house and backyard. My kids loved the creek! The grocery store and restaurants are a short drive away as well.

My family and I had a wonderful time here even in the rain! It’s so cozy and beautiful. We had a blast sitting by the fire to make s’mores. The kids had lots of space to run and play too! The Mountain View was everything you could ever want. I never wanted to leave. Host was very responsive when I had a question. It was extremely quiet and beautiful. The towns nearby were also very charming.

Robert is a genuinely friendly and accommodating host. He was super excited to give us a tour once we arrived. He was also thoughtful enough to leave a little something for us as my wife and I went for our wedding anniversary. If you like a home in the mountains with an artistic flair and beautiful gardens, this place will blow your mind.

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!

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

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.

We had a wonderful time at Tina’s place! Surrounded by woods, but somewhat close to the downtown area (super cute too!), the cabin had all we needed, and is also very cozy, neat, comfortable. Excellent bed and pillows, perfectly AC’d, with a fully stocked kitchen. We are happy, and our pups were THRILLED! Huge thanks to the host.

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.***

Stayed for a weekend with my fiancé and dog. The studio was clean and spacious and included everything you might need. The property was beautiful, scenic and tranquil - and the pool was a definite highlight! The location was ideal as the town of Woodstock is just a quick drive away, which created a perfect balance of privacy and convenience. Definitely recommend and would love to return again.

This comfortable, cozy, magical piece of Catskill paradise was the perfect place to gather to mourn the loss of my father and make some new family memories for a lifetime. Photography is a hobby of mine and the picturesque landscape allowed me to get lost in my passion. We cooked all our meals together in the well-appointed kitchen, challenged each other in the PacMan arcade game and cuddled up together to watch the stars shine and a movie on the comfy couch. We took long walks and met two local farm horses grazing freely in the local fields. The wonderful host was very accommodating and fast to respond. We loved her thorough recommendations for local dining, fun activities and nearby shopping. Book this cabin in the Catskills! You will not be disappointed! We will be back! ". . . there are deeper gorges, greater streams and higher mountains but in no other place is the combination so blended into a harmony so perfect as to form such tempting bits for the camera or the brush.”