House vacation rentals in Windham

Awesome property for a weekend getaway from the city. Sonny made this place into a fun playground - the pond is amazing, the hot tub, sauna, and back deck felt like a spa, and we enjoyed the fire pit and taking a short hike to the creek. The house itself is simple but has everything you need and we even managed to order Uber eats once from Kingston. The area is great, and we enjoyed the villages and a nice hike in the area. We will definitely come back.

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.

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 had the best weekend at the house with our two young children and dog. We loved the house, we loved exploring the property and close by water. We couldn't be closer to town. I can't wait to go back again!

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 👍🏼

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

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.

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.

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!!!

I decided to take my friends to a cabin and make a road trip out of it for my bday and after days of searching for the right AirBnb, I chose James’ house. I did NOT regret it at all. Very private and peaceful location, absolutely beautiful surroundings, only 10 minutes away from everything you might need (gas station, grocery stores, book stores, pharmacy and even a movie theater). The house pretty much had everything that we needed. We weren’t lucky enough to explore the nature more as it rained most of the time, but it only made sitting in front of the fireplace and watching movies more ‘romantic’. The cabin was very clean (not squeaky, but clean enough, can’t expect a cabin to be spotless). It had plenty of firewood for the fireplaces, the grill was gas powered so very easy to use, there was A POT of cutlery, dishes and utensils for anything. In short, if you want to celebrate any occasion or just go and have a peaceful weekend with your friends/ family, this is THE cabin.

This place was perfect for our girls weekend getaway. The space was very private and beautiful with tons of little wildflowers. The deck with the hammock was a great outdoor hangout spot and so was the sun room with its full openable screened windows. So peaceful. The kitchen had everything we needed. It was also located near a cute park with a lake we could picnic at. Host was super nice and made everything easy for us.

We had an absolutely wonderful stay at this Airbnb! The home was spacious, cozy, and even better in person than we imagined. There was plenty of room for our family to spread out, and the assortment of games provided kept everyone entertained for hours. The home was impeccably clean and beautifully decorated, creating a warm and welcoming atmosphere. The check-in and check-out process was a breeze, and Genevieve and Yahve were fantastic hosts. They were incredibly responsive and easy to communicate with, offering excellent recommendations for local activities and dining spots. Their tips really helped us make the most of our stay! Overall, this is a perfect home for families looking for a relaxing and fun getaway. We would absolutely stay here again and highly recommend it to anyone looking for a great place to stay.

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.

Thoroughly enjoyed our stay at the Johnson Cottage. Super quiet area making it so peaceful and house was very cozy. Home was extremely clean and everything was nicely appointed and all seemed brand new. Bathroom floor with radiant heat was a treat. Plenty of space for my husband and I and our 2 older (mid 20’s) boys. All loved golfing at Christman’s & always a great stop at The Chicken Run! Our dog also loved the property and exploring the woods and the extra dog items left in the mudroom for us to use was so thoughtful of the owners:) Would love to return in the Summer & utilize the deck area!

Janet was an excellent host and her home was beautiful. Extremely spacious and clean. One thing that stood out was every (light) switch had a label of what it was for. Kitchen had many appliances and seasonings, master bath had an awesome jacuzzi (and many toiletries), and the hot tub outside was easy to operate. Patio is also a beautiful amenity at night. Overall an excellent experience - can’t wait to come back!

Me and my family really enjoyed our stay. Host was very communicative, gave great suggestions of nearby places to check out, and made sure we were comfortable during our visit. Place has a great view, big backyard, and was very clean. Would come back again for sure.

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.

Our family of 11 had a great time at the house! The layout of the house was great, we all had plenty of room to relax and hangout. The deck had a beautiful view and over all house was great. The bedrooms were a good size and cozy. It was super close to Windham mountain and made for a great location and house for the weekend!

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.

This is a really special place and a hidden gem in Hudson Valley. With its modern architecture, well curated furniture, engaging art, beautiful open fields and a canopy of tall trees all add up to create a truly unique experience. The place has a full kitchen, a big and cozy living room, a patio perfect for lounging and very comfy bedrooms. The strategically positioned glass windows blur the indoor / outdoors. Michael is the perfect host with clear and responsive communication. My wife and I look forward to our next visit!