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

Big Sky Evergreen Retreat

Enjoy a stay at this stylish, classy and comfortable condo in the Big Sky Mountain Village. You'll love the sense of privacy amid the evergreen trees! Stay in with the fully stocked kitchen, or visit the nearby shops and restaurants. The Hill Condos are easy walking distance to the free parking shuttle to the ski resort and village shops during the winter season. Only a 10 minute drive to the Meadow Village for groceries, more restaurants and great summer hiking and cross country ski trails.

Beautiful Triple Level Condo Walkable to the Lift!

(Max 4 adults 2 kids) This newly remodeled triple level loft is perfect for families or small groups and it is minutes to the lift in Big Sky Mountain Village. • 3 Levels, 850 ft² - 2 bed room + additional sleeping areas. •Includes 2 parking passes •Three-story layout permits working remotely or attending online classes •Wifi •smart TV In addition to Yellowstone and Teton national park trip, Bozeman Hot spring bath, skiing and mountain biking there are a lot more to enjoy activities!

Ski, bike, hike, or work remotely at Lone Peak

Enjoy a cozy, comfortable, mountain getaway at this centrally located unit just minutes from Big Sky Resort. This condo’s convenient location and easy access to the slopes make it the ideal outpost for all of your seasonal Big Sky adventures! This unit features 2 bedrooms each with queen beds, 2 bathrooms and a sleeper sofa in the living room. There is a designated workspace in the master with high speed internet. The kitchen is fully equipped with everything you need for a cozy night in.

*3 Level Loft *Lone Peak Views* Skier's Paradise

This Mountain Village adjacent and recently renovated Hill Condo is perfect for your dream Big Sky Ski Vacation. All reservations include local advice on transportation, itinerary and digital guidebook to the Big Sky area, to ensure you make the most out of your time in Big Sky! • Complete Remodel in 2021 • 3 Levels, 850 ft² • Loft with panoramic 180° Lone Peak View • Minutes to the Lifts, Shopping and Restaurants • 3 Distinct Sleeping areas • 4 adults Max, No restrictions on kids

Modern, remodeled ski getaway| prime location

Relax in this beautiful condo in the heart of Big Sky’s Mountain Village with easy access to Big Sky Resort and Lake Levinsky. Close to skiing, hiking, mountain biking and a great home base for all of your adventures. This condo has been completely remodeled. It features a king size bed, an open floor plan, fully stocked kitchen with premium appliances, full bathroom with shower-tub combo, smart tv with viewing from the living room and bedroom, and an in unit washer and dryer

Tranquil 2BR Retreat | Close to Slopes

Welcome to your mountain escape in beautiful Big Sky, Montana! This newly renovated 2-bedroom, 2-bath loft condo offers the perfect blend of comfort, style, and location. Just a short walk to the lifts, you’ll be steps away from adventure—whether you're skiing in winter or hiking and biking all summer long. Located at the base of Big Sky Resort and only a scenic drive from Yellowstone National Park, this condo is your gateway to everything Montana has to offer.

Cozy, Large Condo at Big Sky Resort!

Elegant, colorful, and inviting, this 2BR/2BA condo has fun colorful finishes and furnishings, a fully stocked kitchen, smart TVs in living room and all bedrooms, comfortable beds, linens, down pillows, and art. The perfect place to stay for all your ski and summer adventures at Big Sky Resort and in Yellowstone National Park. You will be surrounded by mountains and steps from the main Big Sky Resort Base Area and the magnificent 11,166 ft.

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

This cozy 3BR, 2BA Powder Ridge cabin offers ski-in/ski-out access via the White Wing run, stunning Lone Peak views, wood-burning fireplace and a private hot tub—perfect for year-round adventure. Just minutes from Big Sky Resort and summer fun at Lake Levinsky, hiking trails, and ziplining. Professionally managed by the local Two Pines Properties team, you’ll enjoy comfort, convenience, and trusted support during your stay.

Cozy get away for 2 overlooking Lone Mountain

Great views & Great location in Big Sky, a 4 minute drive to Big Sky Center. This cozy upscale one bedroom condo is lower level of A larger home that is occupied by the owner. Large private yard with great views Of Lone Mounntain. Fully equipped apartment. Winter Guest can use the cascade lift for ski in ski out access to and from this property. Summer guest will enjoy hiking & the peaceful outdoor space, and wildlife

Cowboy Heaven Cabin Ski-In Ski-Out Hot Tub

Perched at 8,300 feet atop Cowboy Heaven, this rare stand-alone Big Sky vacation rental offers true ski-in/ski-out access right from the deck. As the highest cabin in the community, it features south-facing mountain views, a private hot tub, and cozy interiors with a gas fireplace. Perfect for couples or small families seeking elevated adventure and relaxation.

Studio getaway steps away from Big Sky Resort

This 440 sq ft studio in Big Sky has everything you need to enjoy your trip to the mountains. Walking distance to Big Sky Resort! Ski, bike, and hike then relax with wifi, smart TV, DVD player, and full kitchen. Lone Peak view right out the window. Everything you need is just steps away. Next to the free shuttle route to Big Sky Mountain Resort!

Big Sky Resort Mountain Village Condo - 2Bed/2Bath

Cedar Creek Condo Complex Unit 19 2 bed/2 bath condo with one of the best locations in the Big Sky Mountain Resort Village (walk-out and ski-in). The condo is a clean, quiet, and a smoke free complex with breathtaking views of Lone Peak Mountain.