Ski-in/Ski-out vacation 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!

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.

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.

If your are thinking about staying here just do it. It is amazing. Thee is a pallet stove in the house and the deck that will keep you nice and toasty. There are 2 pools. Owners are very responsive. No question too small. They provide everything to make this home away from home. The location is close to so many activities. It is well worth the money. This was our first girl trip and we even got to leave a token to markwe were there.

We had an amazing stay! The house was wonderful - super clean, tons of space and gorgeous views of the river. Beth responded to all of my messages extremely quickly. She was easy to work with and very flexible and accommodating. I would definitely recommend this house to larger groups; the set up with lots of single beds was perfect for what we needed. There was also a basement full of games that would be just perfect for kids and families. Everyone who stayed would absolutely stay here again!

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!

We had a terrific time. It’s a lovely home- 20 min from Shawnee mountain and steps away from an indoor/outdoor pool facility (depends on weather), sledding hill and small skiing hill with ski lift. I would absolutely stay here again- and highly recommend for anyone with young kids looking to teach them to ski. Very very convenient. The hosts were available for questions and were friendly/flexible. Incredible customer service. We will be back!

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.

Our family had a wonderful stay at the condo in Killington. The location could not be beat! A very short 5 minute walk to the lifts and Snowshed lodge. The complex had an amenity building with pool/hot tub that the kids loved and the condo was quite spacious and clean. Ruslana was a great host and very responsive! There is a solid chance we will be back next year!

Nancy is a responsive host who provides clear instructions and offers local recommendations. The apartment we stayed in worked perfectly for our ski weekend at mount snow with 2 teens. Plenty of room and amenities within to foster a fun and relaxed family weekend. The maple syrup for purchase was a delicious touch. Would definitely stay again if we returned to the area.

Great space, very conveniently located in town. The host was great, and would definitely stay here again

Great spot right next to Okemo! The cabin was better than the photos, felt really homey and clean.

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!

The place was great and just as pictured/described. Joann gave great instructions and was very responsive. We were only there for a short stay for a race, but it looked like a great area I would’ve loved to explore if we had more time. The only thing I didn’t care for was the requirement for to wash and dry all towels before leaving. Since I already paid a hefty cleaning fee that seemed like a bit much. And the washer/dryer is small so this took a couple of loads to get done.

Great house in walking distance of Hunter Mountain.

Dray was thorough and the airbnb was clean, comfortable, and close to everything! I hope to stay here next time I visit!

Marinas little red cabin was perfect for our ski trip! The WiFi is a little rough but we didn’t spend much time on our phones Bring dvd’s (the collection is solid but more the better) Perfect distance to okemo, Stowe is less than two hours so it was great! The cabin felt so cozy and felt right at home! Would def book again!

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!

Perfect place for quiet R&R. Surrounded by nature. Seeing deer in the yard almost daily! Beautiful hiking trails all within 25mins of the cabin. The cabin was well stocked with toiletries and basic kitchen supplies. Thomas was a great host very responsive and helpful.

Host was very accommodating and generous . Please brings you back to simpler day just what we needed to get away from the city

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!

Melissa’s place is amazing. Such a great space - house, sauna, and hot tub impeccably clean, super comfy bed and above and beyond details that made our stay feel like a four star hotel but with all the comforts and privacy of a Poconos air bnb. The master bedroom (which does include a soaking tub w jets!) alone was worth it. We look forward for our next opportunity to stay at Melissa’s!

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.