Family-friendly vacation rentals in Windham

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!

The view was absolutely stunning and the environment was so peacefully quiet. The home is beautifully constructed and decorated with all the necessities and amenities. There’s plenty of space for the pups to run around safely, and the hot tub was amazing, especially with that view! William & Liz were excellent communicators and made the whole process incredibly simple. We’ll definitely be back!

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!

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!

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.

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 house is spacious and elegant. The wooded lot has a pretty creek a little way from the house. We took some walks through the snowy woods and roads beyond the house and could have kept going for a long time - the mountain is peaceful and beautiful. The owners live a few doors down and came by to help set us up before a major snow storm. We had a really nice time.

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 lovely time at Blythe's place. The house was clean, cozy and so close to Bellayre mountain, which was perfect for our ski trip. Would definitely stay there again!

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.

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!

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.

Fantastic place, very private, very peaceful! Couldn’t be any happier staying there for a couple of days with my dog.

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

Eugene and the zen house were so much fun! Its the first stay ive had at an airbnb where i really feel like i have to come 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.***

Three friends met at this beautiful carriage house with the feel of a French chalet! We stayed two nights with varied weather conditions. The house, grounds and location was perfect. Hot tub was used and so relaxing. The surroundings were beautiful and peaceful. The host, Diane was very helpful and friendly. What host makes scones each morning and delivers them warm?! Visited the Ashokan Reservoir trail, Opus 40, and Woodstock. Recommend this home highly. You won’t be disappointed!

My family stayed here for a weekend trip to Windham. The location to the ski area was very close, only 6 minutes away. There were plenty of nearby restaurants, markets, and coffee. The house is clean and cozy and perfect for a family of 4 or 5.

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.”