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!

Where do I begin with how incredible this place is for spending time with loved ones! This house sits beautifully on top of a hill, with complete privacy away from the hustle and bustle. The scenic views from the patio are breathtaking, complemented by a very well-maintained garden and beautiful landscaping. There are lovely areas for peaceful walks throughout the property. This place looks even better in person – beautifully decorated with gorgeous and comfortable furniture throughout. Everyone had the most restful sleep, and even the bathroom chairs were a wonderful touch. Michael and Francis were extremely communicative and accommodating. The fully equipped kitchen is also a huge plus. We would absolutely come back!

We had two families stay at Ali’s place over the weekend. The communication was really good and responsive, directions were spot on. We did not have any issues getting in. The place was as described, it’s quiet, easy to find and all amenities in place. The EV charger provided ample juice for the two Teslas. You will need an adapter for the Tesla charger. There are grocery stores and many bars nearby too.

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!

We booked this home hours before getting there because our prior one was cancelled. The host was so nice and her home is amazing. It isn’t the typical generic air bnb and I was so happy that my daughters were old enough to appreciate how special it is. For our family what made it really comfortable was the bedrooms were spread out on opposite ends of the house and each had its own bathroom - and they are beautiful bathrooms. The windows are huge - and the winter views were crazy - the house is high up with rolling woods and a winding stream below. The furniture, artwork and even the cereal bowls were fascinating to look at. The house is very fresh smelling - no mold or musty odors and was spotlessly clean with quality and comfortable sheets and down pillows - beds were heavenly actually. We drove to Saugerties and Woodstock nearby but mostly stayed at the house though for a wonderful time.

My husband and I stayed here with our 4 teenagers and it was a great space for us. The kids loved the loft area and enjoyed hanging out in that space. Beds were comfy and linens like new. Would definitely return next time we’re in the area!

My family and I had a great time at Delana’s lovely house Craryville is a beautiful place We love staying at Delana’s place and hope to come back for our Thanksgiving holiday next year! Thank you very much

This condo is absolutely beautiful and comfy! We especially love the bed and pillows.

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.

We had a great time staying at Joann’s place! We came here with a group of friends from college and it was a perfect spot to hang out, play board games and a not far from some great hikes (would highly recommend Kaaterskill Falls Laurel House trail). The hot tub is great and the backyard is an awesome place to hang out. Joann was super communicative and responsive and went above and beyond to help with any issues as they arose. Would highly recommend her to anyone!

What a wonderful respite! Casey's home is perfect this time of year, with gorgeous local hiking, restaurants a short drive away, and breathtaking views right outside of the kitchen window! The area was very quiet and peaceful, the property has a creek in the back yard that is private and serene, a wonderful place to meditate and get grounded. The kitchen is recently renovated and has beautiful fixtures, it was actually very fun to cook here! I look forward to coming back with a larger group of loved ones, I know we'll have a wonderful time!

Great house in walking distance of Hunter Mountain.

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.

Mario is an exceptional host. His warmth, responsiveness, and communication were so welcome. The house is exactly as described and comfortable in every way. Mario also suggested local sites and restaurants and they were all worth it. Definitely coming back!

Maxim was a great host! Very communicative and pleasant. He gave very clear instructions and local recommendations. And his responses were always speedy! His home is beautiful, cozy, and very clean. We felt safe and comfortable. We had an amazing weekend visiting in The Catskills and staying here. We highly recommend staying in this beautiful home.

We had a quick Memorial Day escape with my family. The place is actually better than the images and descriptions. Quiet and easy to access. 1 minute drive to a large grocery store - many options to eat, but we loved Bread Alone (9 minute drive). A splendid experience - recommended!

We loved this place from the moment we walked in the door. The decorations are so cute and the VIEW! Definitely has a wow factor and is exactly as described. We loved how dog friendly it was, with little details like a bone jar, dishes, leash and flashlight, and dog wipes at the front door. And the bedrooms were perfect with soft mattresses and ample closet space. It also smelled phenomenal in there with lots of decorative candles and lotions. We had everything we needed in the kitchen, and found that the location was super close to lots of restaurants for eating out. And it was very close to lots of hiking trails and the dog park. We were so sad to leave and can’t wait to come back again!

We rented out the cabin for the Memorial Day weekend and we had a blast. Maria is a kind and gracious host and helped us feel right at home. The cabin was very comfortable and the fireplace was a nice added touch. In addition, the speaker set up was excellent and we were able to stream music throughout our trip. Hoping to be back soon!

Stayed for a long weekend and it was lovely. This place is exactly what you expect it to be when you arrive! The amenities kept us entertained & the views were amazing.

Incredible location for ski in and ski out at Hunter MT. The house is perfect for a family and would recommend to anyone looking to ski for the weekend!

I had a wonderful stay at the Riverside cabin! The place was peaceful, clean, and beautifully set up for relaxation. The hot tub and sauna were definite highlights—perfect for unwinding after a day in nature. The host was friendly, responsive, and made sure everything went smoothly. I’d definitely love to come back!