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

We had an amazing stay at Wanderlust in Windham for our friend’s 50th birthday, with three families (6 adults, 5 kids). The house was perfectly designed for groups, giving the kids plenty of space to enjoy while the adults had their own areas to relax. The ski-in/ski-out access made getting to the mountain effortless, and after long days on the slopes, the hot tub and speakeasy were a huge hit! The house had everything we needed to unwind, celebrate, and make lasting memories. The host was incredibly responsive and helpful—when we encountered a tripped breaker and needed to troubleshoot the hot tub, they provided clear instructions within minutes, making the whole experience stress-free. Overall, this was a fantastic stay that allowed us to focus on enjoying our time together without worrying about the details. Highly recommend for anyone looking for a spacious, well-appointed, and conveniently located getaway in Windham!

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!

Great house in walking distance of Hunter Mountain.

We had an amazing stay! David was quick to respond with any questions I had and even came out to hook up the propane tank for the heated pool. I saw in previous reviews about the tricky driveway but David’s description of it is perfectly accurate and not any trouble, just a little steep but nothing super tricky to deal with! The house has a beautiful setup and view, very clean and so much space. Even though it was cold and rainy we had the most fun and peaceful stay at this home. The bride of the bachelorette group said she wants to book with David on her own just for another stay/get-a-way! Highly recommend this beautiful space!

My husband and I spent a long last winter weekend here. The condo was perfect for ski on/off and we enjoyed a day on the mountain. Though the weather wasn’t great the whole time, Brittany & Jen were quick to send recommendations for things to do, trails to hike and their favorite restaurants. So close to lots of great spots in this little mountain town. We would absolutely stay here again

What an amazing experience! Our kids loved every second of it. Our hosts were amazing, responsive, and inviting. The home was beautiful and the scenery was spectacular. I highly recommend staying here. It was a great life experience! Thank you!

We had a wonderful stay at Eva’s! Would highly recommend! Everything was clean and the house was very cozy. Great location too!

My girlfriends and I stayed for an overnight at this house to celebrate my 60th birthday. It mattered to me to find a place that enhanced our time together. It was such a beautiful place. We loved being there—the look of the rooms, how comfortable it was to hang out there. We had a zoom event planned for Sunday morning, and the TV was able to accommodate our need to mirror from our iPad so we could have a bigger screen for all of us to participate. And the property is just gorgeous! Breathtaking, really. The pond out front and the well-cared-for garden especially. We loved all the thoughtful and beautiful design touches, from the towels chosen to the living room couch to the bench by the pond—so cool and beautifully done! We had multiple conversations during our visit about how much we loved being there and all the touches we appreciated. And we spoke several times about wanting to come back for longer! Looking forward to whenever that ends up being.

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

The Sugar House was a fantastic place to stay! It was quiet and peaceful and there was a ton to explore in Burlington VT. The house had a lot of charm. it was cozy, warm, and had everything we needed for the weekend!

The unit is very comfortable for a family and very convenient to Mount Snow. Updated bathrooms and washer/dryer. Great clubhouse and pool facilities at Seasons condo. Andrew was a pleasure to work with.

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!

Perfect location right next to the mountain. You could tell Kristof put a lot of thought into the unit. Room was clean with all the amenities you need (and some more in case you forget). He was super responsive no matter what time of day. Check in / out was seamless and private parking in the hotel was vital. Will DEFINITELY stay here again if we come back to the mountain!!

I enjoyed my stay here! Gorgeous condo with an absolutely breathtaking view. Decided to stay here for my friends wedding and it couldn’t have been a more perfect spot. Thank you to Paul and family for allowing me to stay at your home.

This place was lovely! Super cozy, very well decorated, and hosts a wonderful view! Judi’s was kind, understanding, responsive, and all around a wonderful host. We came here for a friend’s birthday and he was blown away. Thank you for everything, and we plan to come again soon!

Wonderful place, beautiful location. Would 100% book again

We had a wonderful time in this beautiful rural Vermont oasis. Exactly what we were looking for! The place is quintessential VT…. So if you are looking to spend a few nights in a reconverted barn on farmland…. Well, this is it. We loved being able to walk the property, and the jacuzzi and sauna were a real highlight. Directions getting in and figuring out our building were a bit confusing at first but we figured it out. We had a few small issues but Ben was responsive and did his best to take care of them quickly - with varying levels of success. The outdoor area could use some easier access and a bit more attention, but we were told that it is in the works. We would stay again in a heartbeat!

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!

We had a wonderful stay at Ali and Carson’s cabin! They were incredibly helpful and welcoming hosts. The Mountain View from the cabin is absolutely stunning, even with the rainy weather, it was breathtaking. We also enjoyed exploring the charming nearby towns, and our two dogs had a great time as well. Despite the rain, we loved our stay and are already looking forward to coming back when the weather is better. Highly recommend!

Very clean and cozy, nice private space on the river

We had a wonderful cozy weekend with friends. Leopold’s place was private and tucked away with beautiful snowy Vermont scenery. We went skiing at Okemo (30 min drive) and then relaxed in the cozy living room. The shower was great and the bed was super comfortable. Thank you Leopold!

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!

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.

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!