Family-friendly holiday rentals in Madison County

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!

The Garden Haus

Charming historic log cottage, newly remodeled. Nestled in a rural agriculutural neighborhood, the old historic Ruby Town, with enclosed private backyard and garden. Connect with the natural world and inspire your artist within! Delight in the vintage details and history of the house: 1 king, two twins, and a large open studio space. Enjoy soaking in the vintage tub, dining in the enclosed porch, and eating straight from the garden!

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).

Creekside Mountain Condo

A cozy 2nd story creek-side condo, 10 - 15 minutes walking distance to Big Sky Resort! You'll be able to park your car and leave it be for the duration of your stay. 440 sq ft gives you a private one bedroom w/queen bed, washer/dryer in unit, full bath, fully equipped kitchen and living/dining area. Skyline Bus is the public transportation option and stops about 20 ft from the condo complex.

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.

Lush Ski-in/outᨒHome|Wood Fireplace|Walk to Resort

Welcome to Big Horn 23! This beautifully recently renovated condo is the perfect spot for entertaining friends and family on your vacation to Big Sky! This home's luxurious decor and its proximity to world-class skiing will truly make you feel like you've hit the home rental jackpot!

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.

Hardy Hideaway

Cozy 2 story guest apartment in the heart of world class fly fishing! Only 1 hour from the west entrance of Yellowstone National Park; it won’t disappoint! Stay for a day, week or even a month! You’ll love it here.