Family-friendly vacation rentals in Madison County

Absolutely beautiful home in a peaceful location with great views. This house has everything you might possibly need and then some! We really loved the hot tub with views of Lone Peak! Beds were comfortable and the house was super clean. We hope to come back someday!!

Amazing views and a great location. Felt like home right away. Will stay again.

This place was amazing to stay in. Very big, very spacious for a family of 15! A few spots where the floor was creaky but still good! A few windows didn't open but we were still able to open others and let the cool air come in. Even though this spot was has no air conditioning, it really didn't need it. I think the only time we were really warm was the first day we checked in. But we opened up all the windows as instructed and turned on the fans and it really helped cool the place down. Would definitely stay here again!

The space is nice and big, for a family of 6 we never felt cramped. Had lots of room, activities on the main floor. Nice view, resort is right there.

We loved our stay in Big Sky! The cabin was beautiful and very clean. The beds were comfy and we had everything we needed for a family of four. The cabin is about 50-55 minutes to the West entrance of Yellowstone. We visited the park a couple days and spent a few days exploring the Big Sky area. We had an amazing vacation and our cabin was perfect to come home to after a day of adventures!

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.

Perfect place for my wife and four girls for Thanksgiving ski trip. Loved the wood burning stove, the home was clean, beautiful views, loved the hot tub after skiing. Short 4 minute drive to the ski resort with only 25% of the resort open so early in the season. Would love to come back later in the season and enjoy the ski in/ski out when the entire resort is open. Very quiet and peaceful. Communication with host/two pines was also excellent! One of our favorite airbnb's we've ever stayed in. Highly recommend!

Would definitely stay here again. Was very convenient getting to the mountain every day. We drove 2 minutes and parked in one of the free lots but the shuttle stop is also very close by. Garage had more than enough room for our Suburban. Hot tub was great. Matched the description exactly.

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.

Robert was a great host, very communicative and provided useful information wrt local amenities. The cabin is a what you’d expect from a fishing cabin, comfortable, clean and well furnished with a good WiFi connection. The kitchen was well stocked with cooking essentials. The cabin is located on small bluff overlooking the Madison River and it’s a short walk from the property to the river.

What isn’t there to say about this property! Truly breathtaking…and space for all! We spent hours on the porch and down at the riverside. We definitely will be back.

The Expedition Lodge was Beautiful and exceeded our expectations! The living room was so cozy and comfortable and the fireplace was perfect. The kitchen was extremely well-equipped with everything we needed for our Christmas dinner. Bedrooms were all very comfortable and everything was so clean and well supplied and organized. We absolutely loved staying there. We were so impressed with everything, even down to the beautifully decorated Christmas tree. Excellent communication from the owner...Thank you!

Our group of 6 adults had a fantastic stay at this Big Sky home! The house was spotless and the check-in process was seamless. The location was perfect—close to everything we needed, yet still peaceful and quiet. We visited Yellowstone, Chico Hot Springs and fly fished on the Gallatin. The view of Lone Peak off the deck or while soaking in the hot tub was absolutely breathtaking and a highlight of our stay. Highly recommend this property for anyone looking for a comfortable and convenient spot in Big Sky!

Silver Star ranch was exactly what we needed. It was private and peaceful and a great place to launch two weeks of exploring from. we hit the tobacco root mountains, Virginia, Nevada, and Bannack ghost towns (Nevada & Bannack were our favorites), pioneer scenic byways and scouted dozens of off grid camping sites for next year in the various national forest. For pets, one thing to be aware at the cabin is are the prickly bears (small cactus)... bothered our German shepherds feet some. Local vet in Sheridan was great and gave us a spray to toughen pads while we were out. it really helped. We climbed the area behind the cabin too...good workouts each morning. Jim was a great host and easy to talk to. Thanks Jim!

This is exactly where you want to stay when you visit Montana. The views and the hospitality were amazing! We definitely would recommend this to anyone visiting Montana! Thank you!!!

What a sweet little cabin, walkable to the real estate lift, with gorgeous views. The unit was dog friendly and there were great dog walks nearby. The kitchen was great for cooking meals. Stay Montana were very responsive to a couple questions we had and showed flexibility to meet our needs. While not in the village, I highly recommend this little cabin, which is a quick drive to whatever you need, but remote enough to feel you are above the fray.

This place was perfect! had everything we needed to make our stay wonderful! Wish we could've been there longer. The only thing that hung us up was we got in later than expected and it was dark out. Directions were good, bit without outdoor lighting, some of the landmarks were hard to find and no labeled street signs, or address placards. But all in all, was amazing!

The house was very clean and comfortable, the kitchen has everything you would need. The location is a quick 2-3 min drive to downtown Ennis, but removed just enough to be very quiet and peaceful. Great stay.

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

We had a great time staying at the Stillwater condos. Location is amazing. We had a big group so we rented multiple Stillwater units, two of which were managed by Melissa & her husband. At mountain base I think Stillwater is the best option if you’re looking for an Airbnb experience. My husband and I actually stayed at another one of Melissa’s Big Sky properties in the past which is why we were confident this would be great as well. We went skiing everyday and it was so easy to walk right up to the lifts. We rented our skis so we were able to use the ski valet right at the mountain base which made it that much easier. Clean beautiful home and very responsive host!

Perfect location for a fishing trip to SW Montana. Sleeps 3 men comfortably. Fabulous deck overlooking the Beaverhead River. Very nicely appointed and equipped kitchen and common area. Fished with HR Hoffman, Perfect Drift Outfitters, for a fabulous getaway.

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!

Ric had great communication and the house was in great shape and well stocked with needed supplies for cooking etc…. Even had a massive guide book with info on local eats, fishing etc.

One of my favorite Air bnb’s! I am so happy I found this location. Highly recommend!