Family-friendly holiday rentals in Madison County

Cozy 2BR/2BA Condo at Big Sky Resort

This private condo is just off the slopes of Big Sky Resort. A fun colorful space fully furnished and filled with art and photography created by the owner. It is the perfect place to stay for adventures in Big Sky and Yellowstone National Park. Views of the 11,166 ft. Lone Peak from all rooms create magical moments every time you look out the window. Fully updated with comfortable beds, high-end linens and hosts willing to do whatever it takes to make your time in Montana wonderful!

Big Sky Resort and Lone Peak Views

Amazing Lone Peak views! Enjoy staying in Big Sky, Montana within walking distance to the ski resort. Take a drive to Yellowstone National Park just one hour away. This second floor, newly renovated two-bedroom, two-bath condo is the perfect basecamp for family and friends looking to stay at Big Sky Resort. With world-class skiing, snowboarding,​ and dogsledding an endless amount of activities awaits. After all your adventures, you will be happy to call this condo "home."

Slope-Side 1 Bedroom, Walk to Chairlifts!

This beautiful 1 bedroom Stillwater condo is located at the base of Big Sky Resort. It sleeps 4 adults comfortably in 2 beds (king and full). The condo has a fully sticked kitchen and bathroom, and comfortable living space with dining and bar seating. The private outdoor patio has a bistro set for your use. Parking is free and located right outside the front door. The home is located only an hour away from the West Yellowstone entrance to Yellowstone National Park!

River Stone Cabin

The River Stone Cabin is a modern Montana cabin with internet access that sits next to the South Boulder River. The Cabin is comfortable and warm with bright spaces for friends and family. The location is rural with many guests seeing a variety of wildlife. We are pet friendly with a fee. The Cabin can serve as a convenient base for visiting parks and local attractions or simply as a great place of sanctuary to relax and unplug.

Ski-In/Ski-Out Cabin | Hot Tub | 5 Min to Resort

Welcome to Powder Ridge 3! This mountain cabin retreat offers all the serenity of the mountains, while also offering close proximity to the amenities of Big Sky Resort! Enjoy the spectacular views from the deck while the sun shines and lounge inside by the wood-burning fireplace in the evening. Located minutes away from Big Sky Resort, enjoy the multiple restaurants and shopping opportunities available nearby.

Ennis loft with 360 degree Madison Valley views.

Pronghorn is located 4 miles Southwest of Ennis, Mt. on US 287. The loft is our guest house over the garage and sleeps 4. Our loft is 4 minutes from downtown Ennis. You’ll love our place because of the views, the ambiance, the location, relaxing vibe, fishing access, and 4 mountain range views. We welcome fishermen, hunters, couples, solo adventurers, business travelers, and families (with kids).

Cozy Guesthouse

Welcome to our guesthouse! Dillon is a small town, with so many things to do. Fishing, hiking, hunting, relaxing, and shopping. This house was built in 2004 as a guest house. It's a spacious one bedroom and one bath house. The kitchen and living room are perfect for cooking and lounging. There is a huge, fenced yard. It’s located in town close to restaurants, shopping and outdoor activities.

Morstein Cabin

Restored cabin and bunkhouse in quiet private location within a mile of Dillon. Bunkhouse has twin bunks to sleep two, power but no heat. The cabin is very comfortable year around. Queen bed and full hide-a-bed in couch. Pictures say it all. Firepit for s'mores or cooking on the outside. Horse shoes for a bit of friendly competition. Frequently, deer pass through or lie in the yard.

MOUNTAIN VILLAGE!! Perfect for families!!!

This condominium is located in the Mountain Village at Big Sky. Walking distance to the slopes or ski shuttle is a 2 minute walk to pickup point. Big Sky offers some of the best skiing in the country with no lift lines or crowds of tourist.