Chalet holiday rentals in Windham

The house is so beautiful and unique, and there is art everywhere you look. It inspires creativity! The hot tub and pool are incredible. The house has everything you need to feel at home. It's quiet and peaceful, and the view is out of this world. This is such a wonderful place for a getaway. Our family had a great time, and we can't wait to visit again soon! Olia made sure we had everything we needed and provided great suggestions for things to do in the area. It was an amazing holiday getaway!

A great place to stay. Truly she thought of everything. The only thing stopping anyone from having a great time in this place is just bad luck. The hot tub is so nice, and a lot nicer than a typical at home tub. The chalet was a great space and decorated incredibly. I would recommend this place to anyone.

My stay at Angel’s Airbnb was wonderful! The space was incredible, the features such as the hot tub and the fire pit were great for a fall get away. Angel was very communicative and the location was perfect.

This place was lovely! Super cozy, very well decorated, and hosts a wonderful view! Judi’s was kind, understanding, responsive, and all around a wonderful host. We came here for a friend’s birthday and he was blown away. Thank you for everything, and we plan to come again soon!

It is a very lovely house for a weekend getaway. We really enjoyed our stay during the long weekend. Thank you!

Cozy Silo Home is a perfect description of Olga's home! The silo is really unusual, with lots of windows/lighting and is comfortable and nicely decorated. It's a short drive from Woodstock, which is a fantastic area with lots of shopping, restaurants, etc. It's also very close to great hiking and other outdoor activities. At the house, we spent most of our time outside on the large balcony/patio and cooking meals on the outdoor grill. We booked last-minute and Olga was very responsive, answered all our questions and made things very easy for us. We live in NYC and a weekend in/around Woodstock is a great way to recharge and reconnect with nature. We definitely recommend Olga's silo home for a weekend or longer!! Note: stairs are required to enter into the home and to get to the bedrooms/bathrooms, so don't bring anything too bulky or heavy.

We had a spectacular long weekend here. We enjoyed the clean and simple spaces and especially enjoyed looking at the stars at night from the hot tub. It was so peaceful to be surrounded by woods and yet a short drive to downtown Woodstock. We’d definitely stay here again!

Could not be more impressed with both the house and host. They made our trip a wonderful special experience.

Cedric’s home was great! Exactly as described and nicer than the photos. Cedric was responsive and a great host. Would definitely visit again!

Huge, retro house just 5 mins away from the mountain. Stayed over Presidents’ weekend with 6 adults and 4 kids. Beautiful family/great room with a massive dining table. Very warm and cozy. Bring sleeping masks tho - some bedrooms had upper windows that didn’t have shades (lower had shades for privacy). Would definitely come back!

Wonderful! The house is really beautiful, with large windows and stunning views of the birch forest and a meandering stream. It is very clean, nicely decorated, and cozy. We especially enjoyed the hot tub and fireplace. The kitchen has everything you could possibly need. Nik is friendly and responsive. The location is great too, feels like a nature retreat but an easy drive to restaurants and skiing at Hunter Mountain.

This was a beautiful home, perfect for our family’s weekend needs. The instructions for arrival, the stay, and departure were all very clear and communication was proactive. Thank you

I spent a week at Fouz and Chris's place with my family (8 adults, a toddler and two dogs) and we had very relaxing, enjoyable, comfortable stay. The house is in a quiet, private area and a short distance from places of interest for hikes, restaurants, museums, historical sites, etc. We received great recommendations from the hosts.

This home was absolutely perfect! The host was incredibly responsive and the house was spotless. She truly thought of everything—even welcoming us with a bottle of wine, which was such a thoughtful touch. Thank you for a wonderful stay!

Melanie was a fantastic host. She was responsive and helpful. The house is beautiful, nestled in the trees on your own little piece of the mountain. There are many great hikes and restaurants close by. There is a great little coffee shop and breakfast spot within five minutes. The property even has some little waterfalls and areas to explore. Our daughters had fun playing games in the game room and have developed a love of shuffleboard. We were able to cook dinners and have a nice fire outside under the stars with everything we needed. This is a great house for a mountain getaway.

Ron was quick to respond with any questions we had. The place is spacious and beautiful! The pool was so nice on the sunny days and we even saw a deer walk by when we were in the backyard! Would love to stay here again.

This was a very nice home with plenty of space for our whole group and easy access to the lake. Valentyna was highly responsive to our questions/messages during the stay and provided helpful house rules/instructions. Note that the study area is not a separate room but a corner/nook in one of the bedrooms, so plan accordingly. Overall, would definitely recommend for large groups of 16+.

Our group at a great time at Nataliya’s in Hunter! The lake was absolutely the highlight, we made full use of the kayaks. Hunter itself is a little sleepy even when we went in May but we enjoyed exploring it and nearby Leeds and Tannersville.

This was such a relaxing home to spend a celebratory weekend in! We had a great time at Adnan's home over the weekend. The setting is so peaceful, right on the water and we enjoyed the fire pit one evening. The space is large, with plenty of room for all. The house is a little bit dated, but with that said, it had everything we needed for a lake-weekend! On top of that, Adnan could not have been more accommodating and responsive.

A beautiful, well-appointed, family-friendly place to stay. Teddy's place had everything we needed and more. The beds were comfortable, everything was clean and well maintained, and exactly as described and like the photos show.

Henri’s communications are excellent and his place is beautiful. Upon arrival, you hear the sound of nature and smell of cedar from the cabin. The view from open space is so tranquil and relaxing. The trees, rivers and sunshine made me forget the time. The bathroom and bedroom are spotless clean with high end amenities. And not to forget the heated floor in the Bathrooms! Kitchen is well stocked and cleanly maintained. Climate and humidity are controlled throughout the entire house to feel comfortable at all time. The mattress is firm and can sleep well. The bedroom view is private and something you can only get from here. It feels so cozy. I had a great time with my fiancé during my 3 day stay. I’m a tennis fanatic, and Henri gave me detailed instructions of the courts nearby, so we could play tennis every day! He welcomed us with wine and coffee. Easy access to nearby shops and restaurants, such as Adam’s and Silvia. I’d love to come back for a longer vacation next time!

I had an amazing stay at this cozy retreat in the Catskills! The house was exactly as described and more—clean, well-equipped, and tucked away in a peaceful, scenic location. Waking up to the sounds of nature and sipping coffee on the porch was the perfect way to start each day. The host was incredibly responsive and thoughtful, providing quick responses and making check-in a breeze. Whether you're looking to hike, unwind by the fire pit, or just enjoy the quiet beauty of the mountains, this place is ideal. Highly recommend for anyone looking to escape the city and recharge in nature. I’ll definitely be coming back!

We had a great stay at David’s place. Sleepy hollow lake is a very quiet neighborhood but close to Hudson and all other amenities. The house felt very private and secluded. We had multiple families staying there and the sound did not travel at all between floors. Kids loved playing downstairs and watching movies while the parents could relax upstairs and make dinner. All in all would very highly recommend

We thoroughly enjoyed our stay at the A-frame. We loved that the house was cozy with exposed wood beams and natural wood. There were plenty of board games to enjoy. The water pressure in the shower was great and plenty of hot water. Our hosts were very accommodating. We absolutely loved all the goats. We had a few favorites we got to spend time with. They were so calm and lovable, each with their own personality. We definitely will be visiting again!