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!

Ray’s home offered the perfect weekend getaway for our family. The house is on a beautiful property with a lovely back yard, small bridge and my kids loved the fire pit! Ray was responsive & very friendly! We look forward to coming back again next time!

Choosing to stay in Porter's container cabin was the best decision we could have made for our vacation. It was so peaceful and relaxing. We had daily visits from a beautiful deer, and countless butterflies. We chose to use this time to unplug, and really connect with each other, and we could not have chosen a better place to spend our time. We've missed the view from the front door every day since we've left, and we're already planning to come back next year. Thank you so much for having us.

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.

Jen & Caroline’s place was exactly as described and just what we needed for a Catskills getaway. We even got to see a hometown Saint Patrick’s day parade that Jen and Caroline recommended - and allowed us to check out a little late so we could attend. So sweet. Would recommend for your Catskills vacation.

This is the place to go if you want to be immersed in nature. You are definitely in the woods and surrounded by lush green. There is a pond glistening in your view from the back screened in porch. A lovely spot to have a curl up with a good book.!

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.

It's a magical location with a beautiful forest and reservoir view.

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!

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!

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.

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!

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

We had a great time at Saugerties! Rebecca's house was wonderful. The heated pool and the trampoline were the kids' favorite and they kept them entertained all day. The adults enjoyed the shade under the comfy pool lounge chairs & the spacious deck furniture. The backyard of the house was well kept and equipped so we spent a lot of time outside. The house is very well equipped and it was spacious for 2 families of 4. Everything was functioning well. The house is close to downtown and there are plenty of things to do nearby. Host was super quick to respond back and to help with whatever we needed right away. We def recommend Rebecca's house.

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.***

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 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.”