Ski-in/Ski-out holiday rentals in Windham

We had a wonderful one-night stay at RUBYSTAR HAVEN! The space was spotlessly clean, very comfortable with many luxurious amenities and unexpected special touches. Melissa was very responsive and accommodating, making check-in a breeze. Our stay was cozy and the location was conveniently located. Highly recommend!

We were 6 adults and 4 young kids, and everyone had a fantastic time at Twin Peaks! The house is up in the mountains a bit, in a clearing surrounded by forest, overlooking the valley below, and both the house and property have a great feel. The views - especially from the great room - are reason enough stay here, but the house compliments the views nicely. Well laid out, nice flow, two working fireplaces, comfy rugs/carpets throughout, cool decor, comfortable beds, big finished basement for the kids. We hung out in every room, watched a few movies, cooked good meals, used the outdoor grill, hiked in the state recreation area behind the house, enjoyed watching the deer and turkeys, had fires in the outdoor fire pit, and had a great day of sledding right in front of the house. We also loved skiing at Plattekill Mountain, which is only 10 minutes away. I highly recommend Twin Peaks!

We had an amazing stay at Wanderlust in Windham for our friend’s 50th birthday, with three families (6 adults, 5 kids). The house was perfectly designed for groups, giving the kids plenty of space to enjoy while the adults had their own areas to relax. The ski-in/ski-out access made getting to the mountain effortless, and after long days on the slopes, the hot tub and speakeasy were a huge hit! The house had everything we needed to unwind, celebrate, and make lasting memories. The host was incredibly responsive and helpful—when we encountered a tripped breaker and needed to troubleshoot the hot tub, they provided clear instructions within minutes, making the whole experience stress-free. Overall, this was a fantastic stay that allowed us to focus on enjoying our time together without worrying about the details. Highly recommend for anyone looking for a spacious, well-appointed, and conveniently located getaway in Windham!

Andrey's place was better than the pictures describe. I really enjoyed the heated floors and cozy warm atmosphere. The place was minutes away from Hunter mountain which is perfect for families with children who would like to take breaks at the home after hitting the slopes. Andrey was very responsive when I needed an answer to a few questions. Great experience overall!

This home was absolutely beautiful, with magazine-worthy decor, a cozy ambiance enhanced by candles, and smart speakers in every room. The view right outside the house was truly picture-perfect. Michael was extremely responsive and provided fantastic recommendations for places to visit. We had an amazing time and would highly recommend staying here. We’d definitely love to come back!

What a dream! We loved Martina’s place - the view was incredible, and we felt right at home in the space. We would definitely stay here again.

Great place and close to the mountain. Having the charger made a huge difference for us. We will definitely stay again

The home was absolutely beautiful and fully equipped with anything necessary such as cooking or activities. My guests and I especially loved the two decks with the beautiful view of the lake. Even moreso Valentyna was very helpful and responsive throughout the stay. I would highly recommend!

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.

I recently stayed at this Airbnb with a large group, and it was an excellent choice. The house was well-equipped for our needs, with a pool, games, pool tables, and recreational items in the basement that kept everyone entertained. Outside, the hot tub was a standout feature—perfect for warming up at night after a chilly day. The kitchen and living room had everything we needed, and we encountered no issues during our stay. The host was highly communicative, providing clear instructions and ensuring a seamless experience. Overall, it was a fantastic stay, and I’d highly recommend this place to anyone traveling with a big group.

This is my third time staying at Juris' fantastic home. It is an ideal accomodation to escape from the city when you want to unplug and reconnect with friends and nature. It is also very close to some very fun trails and a short drive to great restaurants and other happenings. Will definitely be coming back.

Brendan’s place was wonderful and he was an amazing host. He was helpful and proactive and provided excellent recommendations. He went out of his way to make us feel at home, but never felt intrusive. I can’t recommend staying here highly enough!

We had a great time at this Airbnb! The beds were super comfy and it was super close to Hunter Mountain for skiing, Kaaterskill falls for hiking, and tannersville for cute shops! The only comment is that the water does smell a little weird. I would recommend bringing your own water for drinking. Also be warned that the pans were stored inside the oven so take them out before you preheat it.

Very clean and well taken care of! This airbnb has all the necessities and so much more. Lots of privacy and great view. There was snow and rain during our stay which made the driveway a bit difficult to navigate but the host got it salted and had a plow come both days.

One of the most beautiful bed and breakfasts I’ve been to in upstate! Morning views are stellar, room was unbelievably cozy, and the organic farm is a treat. The hosts were incredible!

We stayed here for a ski trip with 7 adults and 4 children, and both the adults and kids absolutely loved it.Communication with the host was very smooth. First and foremost, the location is incredibly convenient—just a 2-minute drive from Hunter Mountain Ski Resort. The interior is warm and inviting, with beautiful nostalgic decorations. The living area is spacious and features an open kitchen, allowing everyone to gather, enjoy a glass of wine, cook together, and have great conversations over meals. With three bathrooms, there was never any congestion. We visited in the winter, but we believe it would also be a perfect getaway for a summer retreat.

It was a perfect place to stay for a quick weekend getaway. The place was clean, peaceful, and comfortable. The host was responsive, helpful, friendly, and proactive. We highly recommend this place and hope to return to snowboard!

Max was a great host! Great communication and a great place to stay. Conveniently located right in hunter and close to all your needs. Would stay here again for sure!

We loved this house. The space is even more cozy than the pictures. There's so many little touches that really make the space, heated floors, super comfortable bed, toys and books stashed away for the little ones. The location is about as close as you can get to Hunter skiing, and there's so many cute restaurants and activities around. We'll definitely be back.

Beautiful cabin! Appropriately set back from the main roads such that you feel remote, but close enough to them that it's easy to make the 5/10 minute run into town for whatever you need. Having stayed in many Catskills cabins this one had our favorite fireplace. It's also close to some fantastic trails for hiking.

The place was exactly as advertised and in great condition. Had no issues with access, and the check out list/instructions were straightforward and simple. Couldn’t have asked for much more