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

Our group LOVED staying at this home. Perfect for a big group and the ski on ski off was incredible. The bedrooms were great and they all had their own bathroom which was really nice. There were many thoughtful touches throughout the house, including a boot warmer! We love big sky and would definitely recommend this house!

The house and the area was as described. Beautiful and well cared for. The home was more then well stocked with all the amenities available for a great stay. The views were spectacular and to have a little snow fall made it very enjoyable for the kids who had never seen snow. Only surprise was the alarm going off at 4:00am. Response for someone to come to the house could have been a little quicker. Still a great time and vacation for all.

This ski-in ski-out cabin was a perfect oasis for our group! The host was proactive with communication and everything was as expected. The cabin was clean, cozy, and had a kitchen full of well-stocked pots/pans/oil/seasonings. Beds were comfortable, and the basement room would’ve been great for kids with the bunk bed. Steps away from a lift, we couldn’t have asked for a better stay!

We had a great time at this stay! The ski-in/ ski out access and hot tub were our favorite amenities, along with some wonderful touches from the host. We had 9 guests and it was a packed house, we will definitely be back!

Great Ski in/Ski out location. Nice hot tub, clean and fairly spacious!

Very nice stay. Really nice condo with comfortable bedding. Easy in and out with key code. Warm garage to store skis and boots. Great kitchen best supplied cookware that I have ever had. Great family or friend’s condo.

We loved our stay here!! The view was absolutely gorgeous! We had everything we needed and more. Would definitely recommend this place when in the big sky area!

Cozy, well appointed and clean condo, very convenient location right next to the resort shuttle stop. The kitchen had everything needed to cook full meals, including spices. Ellie was super responsive, checking in to see how things are and jumping to resolve an issue for us without hesitation. We really enjoyed our stay and would happily book again in the future.

This condo is nice and makes the mountain super accessible. The big garage and two master suites were fantastic!

Wonderful stay. Home has incredible views and is very cozy! Hard to wake up in the AM though because the bedroom is dark with no natural light so remember to set the alarm. Super close to the base area. Great value!

Was our 2nd time staying in the unit, and will definitely be our go to place to stay at Big Sky for skiing. Shuttles to the village are quick and easy. The view from the apartment is amazing. Has everything you need to cook in every night.

We loved this house. Very easy ski access, amazing views, beautiful and well-maintained house. Natural Retreats was very responsive and helpful. We had to leave two days early because of weather affecting flights home to Chicago before Christmas, and we hated losing two days of our trip. We would come back to this house for sure given the opportunity. We were advised to get groceries in Bozeman on the way, and I really wish we had. There is not a full grocery store nearby. I made a note to NR that they should replace the pots and pans because all nonstick coating is damaged, so hopefully they replace for the next renter! Other than that, it was perfect!

Our second time staying at this home, this time with snow on the ground. This is a lovely home with all the amenities a family of four could need. Such amazing views and close to get into town for supplies and restaurants. The roads were plowed daily and felt safe moving around. Natural Retreats was helpful with their communication before during and after our stay. Next time we’ll come back during ski season.

This is really a wonderful place to stay. My friends and I really like to live here. During the check-in, there was one bathroom missing the shampoo, conditioner, and soap. Kevin and the cleaner team responded very fast and delivered the needs to the door within half an hour. Really appreciate it!

Location was perfect for a long weekend in Big Sky. Lodging was very cozy! The Association was quick to shovel while we were there. Highly recommend for a couple or a family of 3-4. Highly suggest host update the photos in the listing, as now there are two queen beds and no bean bag chair. One of the queen beds being a murphy bed. Had a wonderful time in Big Sky staying at Mike's listing.

Wonderful home, right on the ski trail, with great views of the mountains. Everything worked as expected. Jill was a pro. Great communication, clear instructions, etc. I would definitely stay here again! Thank you.

If you are looking for a spectacular location and ski in/ski out access to bug sky. This location is for you. Sitting in the hot tub looking out over the mountains and slopes - exactly what we were looking for and we found it.

Our stay at the Cowboy Cabin 13 was amazing, and everything we could have hoped for! The place was clean, quiet, and surrounded by beautiful nature. It offered all the amenities we needed and more! It was also a perfect location from the town center so we were located close to a bunch of great restaurants and activities. Would def recommend!

Our stay at this beautiful mountain retreat in Big Sky was nothing short of exceptional. From the moment we arrived, everything was perfect—immaculate cleanliness, stunning views, and thoughtful touches throughout the space that made us feel right at home. The host went above and beyond to ensure we had a smooth and relaxing stay, offering great local tips and responding quickly to any questions. The location is unbeatable—peaceful, private, and just a short drive to the slopes and local restaurants. Waking up to mountain views and ending each day under the stars made this trip truly special. If you’re looking for comfort, hospitality, and a slice of Montana magic, this is the place. We can’t wait to come back!

Amazing location with fantastic views. House is immaculate and host is very responsive. We cannot wait to be back!

We had an amazing stay at this ski-in, ski-out cabin! While it’s not located on a ski run, the access via the real estate lift made getting on and off the mountain incredibly easy and convenient. The location was perfect for our skiing family, and the breathtaking views made every morning and evening extra special. The cabin was well-stocked with plenty of condiments and high-quality kitchen utensils, which made cooking for our group of 10 so easy and enjoyable. The layout was spacious and comfortable, and we never felt cramped. The hot tub was a fantastic way to relax after a long day on the slopes! This cabin is perfect for families, with plenty of space and all the amenities needed for a cozy and convenient ski trip. We highly recommend it and would love to come back!

Powder Ridge Log Cabin was a great choice for our stay at Big Sky. For us, it's all about skiing so the easy access to the White Otter Lift and access trail made for a great start and finish to our days on the hill. The place is well stocked with all we needed to cook in each night (our choice) and the space was the perfect size for two couples. The private hot tub was a perfect end to the day and was clean and hot and very well maintained (they refill and sanitize after each guest). We would definitely stay there again.