Ski-in/Ski-out holiday rentals in Berkshire County

Robert and his wife are wonderful caring souls that appreciate Art and nature which shows in their back woods retreat to unplug/de screen & get away from life’s constant online hub, a much needed place to get away from it all. Namaste🙏🏼

Absolutely fabulous AirBNB. Super beautiful spot, close to Tanglewood. Amazing kitchen and bathrooms, beautiful antiques, quiet secluded spot but near all the best of the Berkshires. Mai was very helpful with local tips and folding chairs and all. Thank you for a great stay, we look forward to returning!

This home was the perfect place for our family/friends gathering. Location was fantastic - just a short 1-2 min walk to the ski-in spot, making it incredibly convenient for hitting the slopes with little ones. The host was exceptionally informative and friendly, ensuring we had everything for a comfy stay. Kids had fun sledding between the houses and grownups loved the hot tub.

Howard was a great host. Easy to get in touch with and flexible with our early check in request. House was perfect location for a weekend at Jiminy Peak. Would rent again.

Our family had a great stay at Smiling Dog Meadow and looking forward to returning!

Quaint, comfortable countryside home. Whenever we had questions, Harriet and Marie responded promptly. Beautiful surroundings.

We stayed at Kim’s cozy cabin at Jiminy Peak for two nights. There was plenty of space for everyone and the place was immaculate. The place is so clean from the floor to every corner and ceiling, it makes you feel so comfortable and safe, knowing she took care of every detail. The place has a ton of electrical outlets which is a very nice plus this day and age with kids. The location is great as well. A short walk to John Harvards so the mountain is easily accessible. Big tip, since you’re staying at the cabin, rent your equipment and get your passes the night before, it saves so much time. You can be on the mountain without having to walk to the main lodge. We had an amazing time at her cabin and I would highly recommend it. It’s a perfect stay for a weekend ski or longer.

We had an awesome time at Kathryn and Rob's condo. Kathryn was extremely responsive to my many questions, and flexible with timing. She asked ahead of time if we'd like to arrive early because of the impending snow storm which was very considerate. The house was clean and had everything we could possibly need. The kids (10,8, an 5) loved the basement foosball table and numerous board games, and the grownups enjoyed the many puzzles! The bed situation was perfect for spreading out so each person could have their own space. Kitchen was well-stocked and there really wasn't anything we needed that wasn't available. It looks even better in person than in the pictures. In addition, the location was super convenient for getting to the slope nice and early. Can't wait to come back!

Picturesque location! Beautiful and peaceful ! Thanks for a lovely getaway! The WiFi was great and perfect for a day of remote working.

This was a great place to stay as a family for a ski trip! Easy ski on/ski off access to the mountain with ski lockers was a huge plus. Easy enough to walk to a few restaurants. The kids love the movie theater, pool and game room. Very clean and friendly/helpful staff at front desk.

My girlfriend and I stayed at Mike & Anna's cabin for a long weekend with the intention of spending the weekend inside, enjoying a fire, and disconnecting from work and technology. It was incredible, such a comfortable, beautiful, tranquil, and cozy home. We're already planning a chance to go back. Genuinely exactly what we wanted for a cozy cabin with a fire.

We had such a great time at Rob&Julia's place. Very good communication, great location, the place was sparkling clean! I will definitely come back again with my family! One of my best experiences

Diana and family were amazing super friendly, accommodating and checked in on use through out. We arrived later than expected but Diana waited for us and showed us around the property. We even got to see her dogs, meet her family, met the horse on the property behind and great conversations with Diana. She made us feel right at home. She prepped the pool for us, left us some good snacks and offered lots of recommendations. When you visit check out the theater set up, it’s pretty cool with insane sound system and clear video. Comfortable beds and all around beautiful property. If you visit in the summer it is a little warm on the second floor but we cooled off in the pool and just made sure to turn the fans on. It was the perfect birthday trip, relaxing, private and homey. My family and I are already looking forward to the next trip. Thank you to Diana for everything and hope we can meet again! 100% recommend.

Fantastic stay with wonderful hosts! Wednesday and Jim were so kind and welcoming- had a great time in the midst of a fairly sizable winter storm. Would stay again!

We gather with a large group of friends every year and this was an ideal location for our reunion. There is plenty of space to spread out, a well-equipped kitchen, and a spacious dining area. There are wonderful trails to hike (or ski later in the season)

Our family loved the stay ! Place was beautiful, clean and with lots of activities for the kids. Highly recommend and definitely coming back soon.

A Perfect Stay at Elisa's! Elisa's place was absolutely magical! Located in a charming yet convenient resort, this beautifully designed space instantly felt like home. Sunlight streams through the windows, illuminating tasteful décor that balances style and comfort. What truly stands out is Elisa's hospitality. Her communication was warm and helpful, and her local recommendations led us to hidden gems throughout the area. The spotless cleanliness and private garden oasis for morning coffee or evening drinks made everything perfect. This place represents exceptional value—not just accommodation but an experience connecting you to the local community.

Hamilton is a wonderful host and the area is always beautiful and fun.

We had a fabulous time up at Jiminy Peak and being right on the mountain at Shana’s place made it very easy to enjoy the many things to do. Shana is a great host and her unit was perfect for our family of 5. Our younger two tried counting all of the gnomes in every room. We definitely recommend staying at Shana’s place, she is very easy to work with and quick to answer any questions. Thanks again A+

Our second year staying here and making wonderful family memories. The condo was clean and cozy. Gorgeous view of the mountain and easy ski in/ski out. Everything you need is stocked and ready. We look forward to rebooking for next year.

We had a great stay here. It was very close to the ski lifts, and the ski locker was directly across the hall. It made for a very enjoyable and easy skiing experience. Jiminy Peak is a great place to ski at with a variety of trails for all skill levels, and even though it was a school vacation week/weekend, the lift lines were never long. Margaret was very responsive to any questions we had and made the process easy. We loved it!

We had a wonderful time staying at Paul’s place! We had easy access to the mountain for skiing. It was wonderful to have a ski locked to store our stuff outside of the room. In addition to the wonderful accommodation our kids loved the indoor/outdoor pool after a long day on the slopes. Highly recommend Paul and his accommodation!!!

Perfect home base for skiing at Jiminy! It was great for me and my kid plus we got to enjoy the hot tub, pool, breakfast at the country store and dinner at bluebird & co. Justine was a great and communicative host - we hope to return soon!