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

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.

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!

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.

We had a great stay at the Hollywood Bungalow. House was described accurately and had so many thoughtful touches to make us feel welcome. Diana met us upon arrival and walked us around the property and the house. Such a great host! She had generously provided snacks, treats and gave a thorough overview for our stay. We were primarily focused on skiing at Jiminy Peak which was a short 20 minute drive. We also brought our 5 year-old rescue who had the best vacation of her life. She was able to use the fenced-in backyard to run around off leash and even meet a new friend when Jackson's dog visited. Diana even shoveled walking paths in the yard throughout our stay so we could get around in the high snow. The Screening Room is awesome and provided hours of entertainment. Quiet street and picturesque location. We will definitely return.

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

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.

was a great stay loved the room.

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

My children and I had a wonderful time! The unit was immaculate, the views were lovely, and there was plenty to do at the hotel. Paul was the best host! We had a car issue and had to extend our stay. He was polite, quick to respond, accommodating, and he took excellent care of us whenever we had any questions or concerns. We are looking forward to visiting again!

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!

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!

A really relaxing couple of days in an area that we didn’t know. It’s a beautiful cabin with a lovely hot tub and comfortable beds. Lots of nice places to visit and a friendly general store a short drive away (thanks to Thomas for the info on that). The temperate dropped but the cabin stayed warm even without the main log fire. Clean kitchen and bathrooms, lots of useful things like tea coffee herbs and sauces. Would definitely recommend!

Ben's cabin is nestled in a beautiful location. His cabin is beautifully decorated with unique rustic antiques. The centerpiece of the cabin is the big fireplace that makes the space warm and cozy. There is a hot tub on the patio and a private outdoor shower that must be a delight on a hot summer day. The cabin offers the basic amenities for a comfortable stay. Ben is a responsive host. We would recommend and love to stay 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!

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.