Ski-in/Ski-out holiday rentals in The Berkshires

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!

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!

Welcoming, tidy and clean home. Fully functional and amenable to families with young children. A perfect winter getaway spot given its proximity to Otis Ridge. Extremely easy to ski in and ski out. Mary Kay is a lovely host- extremely responsive, helpful and flexible.

We came up to celebrate a 40th birthday. Jason’s home was absolutely beautiful and exactly what we were looking for. We had a great time relaxing playing games and soaking in the hot tub. Pictures of Stratton Mountain do not do it justice, it’s so much closer in person and stunning. We loved the fireplace indoors and the outdoor fire pit. We had great weather so we were able to utilize the fire pit and then fireplace at night when it was chilly. Very cozy vibes! We would absolutely recommend this gem and would love to come back! Also, Pearl’s Place Southern Kitchen was delicious, get the bbq!

This was a beautiful, peaceful cabin to spend a relaxing weekend in! We loved the porch overlooking the river, and the living room space was so cozy. Everyone was super friendly and helpful. Absolutely recommend this cabin for a perfect Minnewaska getaway!

Place was great! Less than 10 minutes to Mount Snow. We had fun playing ping-pong, air hokey, pool, and darts! Relaxed by the wood burning stove. Lots of rooms and beds.

Beautiful surroundings. Great energy inside and out of the house. The stars at night were just amazing. We had a wonderful stay at Hannah’s place. I would definitely stay again.

Jay's home is easy to arrive at and make a home away from home in minutes. It was clean, inviting and quiet! We enjoyed the quick ride to the ski slopes and the walk to Phoenicia's antique mall. The home is well-stocked and made cooking a meal at home no problem. Jay answered our questions within moments and made the stay relaxed and truly a get-away. We highly recommend his delightful home.

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

Nice place, probably better in summer than winter, simply due to more amenities (like screened porch) and better able to appreciate the location, but it was nice as a winter spot, too, to sit and read by the fire. Kitchen was well-equipped, and the place was very clean.

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.

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

We stayed at Beth’s place in April. The place did not disappoint!! Beth thought of everything!! Our 20 yr old granddaughter stayed in the apartment. Absolutely great space. The view was stunning!! The place was extremely clean throughout. All the rooms are set up to relax and enjoy!! The basement was a wonderland for the kiddos. Every toy, game, and wide open space to play. It was a delightful stay.

Great house in walking distance of Hunter Mountain.

This is a lovely home in a beautiful setting. It is quite close to Stratton and the hosts were all great communicators with a quick response time. I hope to stay there again sometime!

We always book with Dawn! Her place is amazing. We feel right at home. She ensures the house has everything you could need in case you forget something. There are extra details to make your stay more comfortable. Her linens are softer than mine at home! There is plenty of space for my family of five to stay comfortably. I highly recommend booking here! We can’t wait until our next stay here.

Excellent place to stay considering the location and and beautiful views. Owners were excellent, very helpful and did what ever they could to make our experience enjoyable!

We had an amazing stay at this beautiful cabin! From the moment we arrived, everything was perfect — clean, cozy, and even better than the photos. The attention to detail really made it feel like a home away from home. The location was peaceful and secluded, but still close enough to local attractions. The host was incredibly responsive and thoughtful, leaving us great recommendations and little touches that made our stay extra special. I can’t recommend this cabin enough and would absolutely love to come back!

We had a wonderful time at Erica’s place! We enjoyed the firepit and outdoor grill, while our dog enjoyed relaxing on the porch and running around the front area. It was very close to the river which you could hear anytime you were outside, adding to the atmosphere. Both in and outside the house, it seemed she had thought of anything we could possibly need! It was a beautiful cabin, fairly private and quiet, and just what everyone wants for a get-away trip. This was my first time booking with Airbnb, and she made our trip easy from the initial communication prior to booking until the final day when she offered us an additional day due to inclement weather during our stay. I would certainly recommend this cabin to anyone looking for a relaxed trip near water!

Very clean and cozy getaway just a 10-20 minute drive from various gorgeous hikes! Note it is not a unit that gets great sunlight, but we were only there for dinners and sleeping so no problem for us at all. We cooked a few times thanks to the equipped kitchen!

Cliff is very easy to communicate with. The house is in a great location, easy to find, and close to several ski resorts, making it very convenient for skiing. The room is comfortable and warm, and the kitchen is well-equipped, allowing you to cook your own meals. The game room, in particular, is a paradise for children, with countless games for you to enjoy. This was a wonderful experience, and I will definitely come back in the future.

I believe one of the best compliments to any AirBnB host is returning to their property: this was our fourth visit to the Clack Cabin, and surely not our last! We love the Clack Cabin for its coziness, comfort, and location. It's a small space, but has absolutely everything one needs. It's incredibly peaceful and relaxing, with the stream providing such a soothing soundtrack. The Clapper Hollow State Park a few steps away from the cabin has many easy and quiet paths to explore (we had the forest entirely to ourselves on Easter Sunday!). Clara is a wonderful host, very welcoming and helpful with local tips and knowledge. We already look forward to our next visit!

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.