Chalet vacation rentals in Windham

This was our second year staying here with friends, and we had such a lovely time. There's plenty to do inside the house itself even on a dreary day, with curiosities and art abound, instruments, games, fireplace, etc, a great kitchen for group meals, and spacious and comfortable rooms otherwise. Olia is very kind and responsive, with plenty tips for the local area. We'd recommend for groups or families in an instant. Nothing like relaxing in the hot tub while looking out at the mountain vista with rain pattering on the porch roof above - pure bliss.

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.

Great place that was clean, comfortable and cozy. There were excellent instructions for everything and my family loved the hot tub!

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.

very cosy for friends of 4. There are so many details of arts and family history in the house, respect that!

Such a great and cozy stay! Minutes from town center and Windham, so easy to check in / check out. Very happy we stayed here!

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.

Very comfortable, relaxing cottage with nice outdoor space, natural setting, and only 5 minutes into town

My family and I had the most amazing time at the Blue Spruce Chalet! From the start, Cedric made the entire booking easy and seamless. Once arrived, they were so thorough with information in the cabin they provided that there was absolutely no need to contact them, everything was thought out perfectly!   The cabin itself was wonderful.  It was pristine, the perfect location…close to town but secluded down a private lane, which made it feel even more like an escape.  The views were incredible.  The fireplace was a great gathering spot. The garage was converted into a ski room.  I said I felt like I was at a ski concierge at a 5 star hotel.  The kitchen was perfectly stocked.  Skiing was close by, we chose Hunter which was an easy 20 minute drive, and Windham is even closer.  Even our dogs loved it.  Though it’s not fenced in, it’s a large lot and gave them lots of room to play and run. We will certainly be back!  

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!

Lovely stay with family and friends. The host went out of his way to ensure our arrival was smooth, even with a very icy driveway and up to two inches of snow falling. The space is beautiful, secluded and serene. But also close to restaurants in Mt. Tremper and good hikes.

Beautiful home, even better in person! Clean and cozy. Each room was stylishly and uniquely decorated. Great for large groups.

Had a small weekend trip away in the mountains. The group had a blast. The landscape was beautiful. It rained one night and snowed the next, so we spent a lot of time indoor; but the place is beautiful, and we definitely plan to come back in warmer weather for a longer time!

Rebecca and Curtis were wonderful hosts. The mountain view alone is worth every penny paid and the space was peaceful and beautiful. We are a family of 5 (2 adults, 1 child, 2 pets) and the rooms were very spacious and clean. We appreciated the quality of every detail, from the fire pit and outdoor dining table to the cookware. Most major amenities (supermarket, Walmart etc..) are 25 min away which was fine for us. We will be back again. Thank you, Rebecca and Curtis, for allowing us into your lovely space!

My wife and I stayed at Ron’s place for five nights for a winter getaway. We had a great stay, highlights include a comfortable king bed, a quiet setting, a cozy fireplace, and the large ground floor bathroom that feels like your own spa- we thoroughly enjoyed the sauna, huge bathtub, and rain shower. Ron was a great host and was very responsive with any questions we had. We spent many hours watching TV on the screen and projector set up, we grabbed more pillows from upstairs to add some more cushion to the leather couch downstairs.

We had a wonderful stay at Tony & Ines’s place! The hosts were very responsive and helpful. The house itself was cozy with plenty of space for our group of 5. The surrounding area was beautiful and super convenient to local ski mountains. Will hopefully stay again!

The house was very fun and accommodated 16 people very comfortably. Valentyna was so great and texted me reminders of what was expected of me and all the guest in a way that felt helpful and not demanding. I loved my stay here and would definitely recommend to any person looking for a fun relaxing time!

The house was well stocked, neat and clean. The property has lots of great outdoor space to relax in. Nataliya was very responsive. Thank you.

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.

Charming, practically brand-new riverfront cabin! We were among the first guests to stay at Henri’s beautiful cabin and couldn’t have asked for a better retreat from New York. Perfectly situated between the lovely towns of New Paltz and Kingston, it offered the peaceful escape we were looking for. Henri was incredibly accommodating, thoughtfully leaving us groceries that made cooking and relaxing on the outdoor deck effortless and even more enjoyable.

This place is amazing and top notch! The perfect house in the perfect location, with a wonderful host - TJ outdid himself! TJs house is spotless with so much room for families/large groups, and the views are breathtaking. The fire-pit, kids play area - every detail was thought of and we couldn’t appreciate it more. Drinking my morning coffee on the master balcony while looking at the lake, I can’t wait to come back! We are already planning our next stay here. I would highly recommend anyone to stay here! Thanks TJ!

We had a cozy winter stay at the lake house, which had a well stocked kitchen, two living areas - great for when kids wanted to do different things - and a thermostat on every floor. Loved that the TVs came with streaming and DirecTV, which really helped when the weather wasn't good enough to be outside. Walkway does get icy in winter but views were still beautiful. Games and activities are more geared toward elementary and older kids, so if you have young kids you'll want to bring things to do. Layout wise, would add that the workspace is in an upstairs loft area (no door). 10 min drive to town and restaurants. Hosts were responsive. I bet it's amazing in the summer!