House holiday rentals in Windham

Very enjoyable time here! Instructions, accommodations, and overall experience was perfect!

Rick's House (Hemlock House) was a wonderful getaway! We unfortunately didnt hit the best weather but the house was perfect for a cool and rainy long weekend both indoors and out. The open first floor with huge kitchen was great for hanging out and cooking with alot of cozy nooks to read and relax. There was a lot of various outdoor spaces and decks to lounge on as well and the hot tub was perfect for the cooler cloudy weather. The bedrooms were all comfy and each room having its own bathroom was another plus. We all loved the sounds of the creek and being able to walk around the trails in the back. The House is in a fantastic location - only 10 minutes from Rhinebeck which has everything you need and is great for walking around, shopping and dining. Rick was informative and provided a great guidebook with clear instructions and local resources and recommendations. Thanks for a lovely stay!

My husband and I had a wonderfully relaxing time at the Little Owl Teahouse. It’s a cozy and well-outfitted cabin with a super comfy bed and a great leather reading chair. Drank lots of the delicious mountain well water. Made breakfast in kitchen — love the pans and electric cooktop. Short drive to Woodstock for dinner. And oh the beauty of the surroundings - scenic views everywhere. Our two little doggies were happy to romp in the fenced in yard. Little too chilly when we were there but pool looks so appealing. Lisa is a proactive and super responsive host.

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

The house is really gorgeous. Everything was very new/modern, clean, and comfortable. We enjoyed cooking meals in the kitchen overlooking the stunning view out the back. The hot tub and fire put were nice amenities to enjoy. The BBQ seemed to not be working, but other than that, no complaints. Location wise, the property is located in the northwest Catskills, near Stamford, NY, and convenient to many hiking spots in the area as well as nearby towns. The property itself its up on a hill, in what felt like a secluded and private spot, which made it feel like a real getaway and retreat. In sum, recommend this Airbnb for the nice amenities, modern touches, and amazing view.

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 property is beautiful! The house and amenities are actually just as nice in real and every detail was so thought out. Arp really has good taste and communicated well throughout our stay.

The cabin is incredibly charming, comfortable, and relaxing. Located on beautiful grounds, very private, but a fairly short and beautiful drive to nearby towns. I hope to stay again!

I left Sam's Airbnb this morning, and I can not say enough about our experience! I am a little late to the Airbnb game, but I am so grateful that everything about this trip expell my hesitation. There was ample room for my family and the dogs to have space to breathe and (most importantly) privacy so we don't hear each other snore and talk in our sleep. There was a beautiful view of a misty mountain through the living room and double bed room windows. Be prepared for there to be zero cell phone reception, but wifi calling works great. I started GPS while still in the house, it kept up just fine without signal. Besides, if you get lost, I promise you the scenery is worth every wrong turn 😀

This was the perfect AirBNB for a trip I took with 5 other friends! Richard was quick to response, answered all of my questions leading up to my trip and shared many recommendations. Easy and seamless stay!

My friends and I loved our stay at Wilderkaat. The cabin was clean, comfortable, and well supplied with thoughtful amenities. We immediately felt at home and were able to relax and enjoy our time there -- we only wished we could have stayed longer.

We had a wonderful stay at this house! It was incredibly convenient to Windham, had everything we needed/wanted in a weekend getaway. The house is excellent for all ages with the most spectacular windows and views. The hosts were also super responsive and accommodating. Definitely highly recommend to anybody visiting Windham.

Excellent communication! Thanks so much!

Amazing host and amazing home which made my friends and I fit right in and feel comfortable. Cant wait to come here again maybe one day for longer, super easy to just chill and relax, the hot tub is too good!!!

Such a beautiful space and property. We went for a girls weekend and all 6 of us had our own bed! We loved the interior design and the patio space looked really great although we couldn't use it because of snow in spring. Will definitely book again in warmer months!

Great stay! Marquis was very responsive and helpful. Great house for a weekend ski trip.

Maryana & Scott literally saved our group’s weekend (and sanity) after our RV had flooded and ruined our original camping plans. After frantically shooting out messages to every nearby Airbnb that looked somewhat doable to see if our RV would fit, they were the first to respond by a long shot and were so thoughtful and attentive to detail from the jump to make sure we had what we needed. The place was spotless when we arrived, and gave us a space to finally relax. The backyard is gigantic, beautiful, and so well equipped we ended up cooking dinner out there and hanging out for most of the night to at least enjoy the outdoors. We were able to make the most of a bad situation thanks to Maryana & Scott, and I cannot thank them enough. Would love to stay at any of their properties again in the future, they’re just all around A+ human beings.

Amazing place to get away from the city! Close to all of the big windham attractions yet super peaceful and private. The cottage itself is very comfortable and the kitchen offers everything you need to cook a nice meal. We also had deer and wild turkey roaming in the large yard out back. Highly recommend!

Thanks for a great stay. We loved the location and proximity to the mountain. Your place was clean and comfortable.

This was such a cozy get-away, we loved it!

Jessica’s house is likely my best Airbnb stay out of nearly 100 so far! The place feels so much like home, with many warm and personal touches. I can’t say enough about the beautiful surroundings. The property consists of a large lawn, very nicely maintained, and surrounded by woods. We encountered rabbits and deer, apart from the calming sounds of birds all around. The creek is a short walk away, and holes to the waterfalls are close by. If I had a choice, I would never leave! We had an absolutely amazing stay, I recommend this to anyone who likes peace and nature.

We had a wonderful time staying here over the Christmas holiday. The house was comfortable, clean, and well-equipped with everything we needed to cook, which was especially helpful since most restaurants were closed for Christmas. Its location is fantastic, close to ski resorts, restaurants, and beautiful sights.

Lori’s home was a perfect ski getaway for my group of friends - Comfortable, clean, and super cozy. A short drive to Windham Mountain, this home has easy access to all of the great things the Catskills have to offer. Beyond that, Lori was incredibly responsive and helpful. Can’t recommend this place enough!