Ski-in/Ski-out vacation 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!

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!

Beautiful place and stay! Private, cozy & peaceful, yet close enough to fun places like Hudson and Kingston. Martina was a wonderful host, super responsive with tons of great recommendations. We absolutely loved our stay!

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

this place was amazing. closest place to the mountain. walk out of the yard right into the parking lot. place had everything you needed and a bunch of extra games to play too

This was our second year staying here for our winter trip and we love it!

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.

Had a lovely time! It’s a beautiful house and Juris sent very clear and helpful instructions before check in. Would stay again.

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.

My friend and I had a lovely stay at Highlander’s View and Leam was a charming host. The highlight of our stay was a late evening dip in the hot tub … the sky was big and full of stars, the air was crisp, and the hot tub was toasty—a perfect evening in a rolling rural location.

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.

max was an amazing host, very responsive and very friendly. The house was clean and very cozy. loved everything about it.

We booked this Airbnb for 8 people, and it fit us perfectly! Having two kitchens and two full bathrooms was super convenient, and the units were just a few yards apart, so we had our privacy while still being close enough to hang out easily. The space was clean, comfortable, and well-equipped for a group stay. Highly recommend for families or groups of friends who want to vacation together but still have their own space. Would definitely stay here again!

The perfect long weekend retreat! Max and Fallon’s place is so cozy and clean, and we loved how they decorated the place. Very simple check in/out instructions and easy keyless door lock system was very convenient. The location for ski in/out couldn’t be better - we only wish we found this place earlier in the season so there was more snow! One day I had a take a Zoom call for work and had no issues with the WiFi. The water pressure/shower was great. We really appreciated the nearby restaurant and shopping recommendations and there was a nearby grocery store which was convenient. It was the perfect space for a couple + dog and loved that it was pet friendly with a water/food bowl :) they had everything we needed and appreciate the hospitality! We will be back!

This is the ideal getaway for multi-family ski trips! Catskill Oasis I, II and III gave our group of three families the perfect balance of togetherness and privacy. Each suite had its own ski-in/ski-out access, full kitchen, and cozy living space, with pull-out beds for the older kids and cribs for the little ones—super convenient for families with children of all ages. We loved being able to enjoy the mountain all day, then unwind separately in our own suites. The discounted rate for booking all three properties made it an amazing value. We’ll definitely be back!

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.

Stayed here for a Bachelor party to escape the hustle and bustle of the city. Everything was perfect. Loved all the fun stuff in the house like the sauna, hot tub, movie theater, darts, and pool table. Would highly recommend!