Family-friendly holiday rentals in Madison County

I rarely leave reviews but we had such a great experience with our stay at this cabin that I had to share. From before check-in to checkout, the host was thorough with their check in instructions and check in reminders and follow ups. The cabin was GORGEOUS and had plenty of space for our 9 guest. We had 4 couples and one other guest and had plenty of place for sleeping, bathrooms, lounging and eating space. The hot tub was ready from night one to enjoy which was so nice in the chilly December month. The cabin is SO close to the resort that it’s a very short drive. The kitchen was fully stocked with all the amenities and utensils you’d need for a long stay. The decor was so cozy and made you feel right at home. I would recommend this cabin to anyone and would LOVE to come back and stay again. Thank you so much Big Sky Rentals!

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!

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.

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

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.

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 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!

We rent a different condo at Big Sky every year so we have a lot to compare Deb’s place with. We’ve never stayed in a condo that offered such a great combination of convenience and luxury. The place is spacious, attractive and well-maintained. The kitchen is fully equipped for cooking and even stocked with spices and condiments. The hot tub works great and offers a view of Lone Peak. The Skyline bus picks up just steps from the condo. We had a great stay and highly recommend!

We had an awesome stay at Big Sky! We felt so welcomed as soon as we walked in the door and appreciated the special touches that the hosts went out of their way to provide (delicious coffee, easy to follow instructions for fire place, towel basket ready to go for the hot tub, propane and a new grill etc.). The property was well maintained and we enjoyed our nights outside in the hot tub under the stars - along side some friendly wildlife. The house was very clean (as was the hot tub) and the beds were sooo comfy. We would highly recommend!

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.

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!

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!

Great cabin . Easy check in process . Host was very responsive . Awesome views of the mountain . Short drive into the town area of big sky.

I needed a complete change is scenery and chose the upper Madison Valley for the fishing and scenery, and it did not disappoint. Chris and Rob were excellent hosts and helped us by recommending what were must sees and what we could skip. The apartment has everything we needed for a nice week’s stay. The views are spectacular.

Highly recommend staying at Keri’s place😊 we felt right at home too!

Perfect space to meet up with family. Felt right at home! The stars at night are indescribable. Plenty of space for a large group. We definitely would like to come back!

I had a wonderful stay at this cabin near Yellowstone National Park! The location was perfect. Close enough to the park for easy access but tucked away in a peaceful, scenic spot. The cabin itself was spacious, clean, and had everything we needed for a comfortable stay. It was well equipped with all the essentials and more. The host was very responsive and friendly, which made I had a wonderful stay at this cabin near Yellowstone National Park! The location was perfect—close enough to the park for easy access but tucked away in a peaceful, scenic spot. The cabin itself was spacious, clean, and had everything we needed for a comfortable stay. It was well-equipped with all the essentials and more. Ben was very responsive and friendly, which made the entire experience smooth and stress-free. I would definitely recommend Ben’s place to anyone visiting the 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.

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.

Condo was perfect, walking distance from Big Sky resort for 3 day conference. Condo had everything we needed for our stay

Our stay the last week of September was absolutely perfect! It was everything we expected, plus so much more. From the time we pulled into the drive way, Pam was lovely to work with! She walked us through the few things we were responsible for during our stay and getting us into the home, and the welcome book was a very nice touch for all of the other information! The home was spotless and very cozy. We were so excited about the views, which were absolutely breathtaking. We got to see deer and pronghorn everyday during our stay. Our main worry was no AC, but the home had multiple portable fans (if you’re someone from the south), though the weather was perfect while there, and a simple open window was all we needed. The town of Ennis is so nice, with some lovely restaurants. I highly recommend getting coffee at On the Fly Espresso. The owner was amazing to us during our stay. The home was the highlight of our trip!

Comfortable place, in an extremely peaceful setting. Cory was kind & super responsive. my family had a great time here. We especially loved the wraparound porch, it was such a lovely place to have coffee & meals.

great folks to work with. beautiful location