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

We absolutely love the location and the place was better than advertised. We created memories that will last a life time and we will definitely be back!!! Thank you.

Great place with all we needed, close to where dropped kids for lessons, loved having ski in (we stayed late in the season so the lift for ski out was only open the first day of our stay), great house and great location.

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.

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

Chris is an A+ host! Very communicative and quick to respond on all questions about the local area and about the condo itself. The kitchen is fully equipped to prepare meals for large groups if needed. the garage and mud room were a big plus to have with all the ski equipment as well. Overall very comfortable and amazing location. The condo is super close to the mountain via car or lift access. we can't wait to come back!

Jenna made our stay delightful and easy to navigate. It is a wonderful spot if you are a skier and want ski in/ski out access to Big Sky. Thanks Jenna!

We had never been to Big Sky, and found this cabin from a search. It exceeded our expectations in every way. Two Pines management was always responsive with our questions providing accurate and clear information. No ski in/out lodging is going to be inexpensive, however this stay was a great value with its full kitchen and washer/dryer with other home amenities. It offered our family a great ski vacation!

Wonderful stay in a perfect condo. We loved it and the family of 6 we had enjoyed the trip a ton. Would definitely stay in this condo again and we’re already thinking about our next trip back to big sky. Perfect all around!

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.

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!

Had a great time being so close to the slope at Greg's place. Skiing right back to the condo was so nice at the end of the day.

Alex was very responsive and the place was great. Very clean and looked just like the pictures. I would stay again.

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!

Absolutely beautiful place to stay!! The home was spectacular and the views were amazing

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.

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.

The home was in such a beautiful spot. Enjoyed the views and area. The house fit our families well. The addition of a second living area was wonderful for our grandchildren if they wanted a place for themselves. Seeing wildlife walk by was very special.

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 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!

Lakeside Cabin #19 in Moonlight Basin, Big Sky, was the absolute best. Incredible views from every huge window as well as from the great hot tub! Wind your way up the mountain past the elk and stunning scenery to this lovely “cabin” with all modern amenities. We enjoyed the deck! Response time was immediate and friendly as can be for the few questions we had. Rented e-bikes (BlackTie), went fly fishing with guides (Gallatin River Guides), spent a day in Yellowstone, and a day in Bozeman at Hot Springs and in town. Terrific location, great people - fabulous week with our family.

Beautiful home! Ski in and ski out. We had the most wonderful stay.

We had a great visit! The space was beautiful with a well stocked kitchen (pots, pans, popcorn maker, blender etc.) and unmatched views. Would recommend in the fall for sure. it is near the big sky resort and many hikes, the golf course and a cute downtown.

Be extra careful walking on the garage floor especially during winter as it is super slippery and even worse with cold ski boots on your feet. Great hot tub with nice kitchen, dining, living area.

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!