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

4.98 out of 5 average rating, 59 reviews

A spacious living area is furnished with a large brown leather sectional sofa and two armchairs in a rich purple hue. A round coffee table sits centrally, and large windows frame a scenic view of snow-covered mountains, allowing natural light to fill the room.

Apartment in Big Sky

Luxurious Ski-In/Ski-Out Retreat

Looking for a classy, upscale home with great outdoor and indoor entertaining space that you can ski or hike right from the back door - this is it! With a private hot tub, cozy outdoor fire pit couch area to lounge, another BBQ/Dining deck off great room, bonus sitting area, amazing views, live edge dining island for 10 - it has it all! Walk to Big Sky Mountain Village year round activities, conferences and dining. Newly built 2022 with a 24/7 local, family owned property management service.

ValueLocationAccuracy

A comfortable living area features a green sofa positioned across from a wall-mounted TV. A round table holds magazines and decorative items. Natural light filters through large windows with soft drapes, while a piece of wall art depicting a tree adds a touch of nature.

4.95 out of 5 average rating, 181 reviews

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.

ValueLocationIndoor spaces

A comfortable living area is showcased with a light blue sofa adorned with vibrant throw pillows. A dark coffee table is centered on a colorful area rug, while a mid-century-style armchair complements the space. Natural light filters through a large window, offering scenic views.

4.94 out of 5 average rating, 216 reviews

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.

LocationValueWalkability

5.0 out of 5 average rating, 110 reviews

The kitchen features modern stainless steel appliances, including a stove, oven, and dishwasher. Light wood cabinetry complements the subway tile backsplash. A doorway leads to a full bathroom, and utensils hang from a rack on the wall, enhancing the functional design.

Apartment in Big Sky

Remodeled 1st Floor King Condo|Walk to Ski Shuttle

Relax in this beautiful 1st floor 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

ValueFamilySkiing

The exterior of Cedar Creek Condominiums is showcased, featuring a welcoming sign that includes the property name and address. Lush greenery surrounds the area, with trees and shrubs providing natural beauty. A gravel pathway leads to the entrance, illustrating the inviting atmosphere of the complex.

4.94 out of 5 average rating, 130 reviews

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

Cedar Creek Condo Complex – Unit 19 Enjoy one of the best locations in Big Sky Mountain Resort Village with this 2-bedroom, 2-bathroom ski-in/ski-out condo. Conveniently located for easy access to the slopes, this clean and quiet retreat offers breathtaking views of Lone Peak Mountain. Whether you're hitting the trails, exploring the village, or simply relaxing, this comfortable mountain getaway provides the perfect combination of convenience, comfort, and spectacular scenery.

ValueFamilyBathroom

A welcoming living area features a stone fireplace and wooden ceiling, creating a cozy atmosphere. A large dining table is surrounded by black chairs, while a comfortable seating arrangement invites relaxation. Large windows allow natural light to fill the space, showcasing mountain views.

4.79 out of 5 average rating, 112 reviews

Ski in/Ski Beautiful 3BR/3BA at Big Sky Resort

The perfect spot to visit Yellowstone National Park, this Ski in/Ski out Townhome at Big Sky Resort is located just a short walk from the Big Sky Mountain Village and just a few feet from Back Bear Poma Lift. It is the perfect place to come back to after a day of skiing, hiking, fishing, mountain biking, rafting, or a day spent exploring Yellowstone National Park. This condo has what you need to enjoy your next holiday getaway in the beautiful mountains of Montana!

LocationValueLayout

An aerial view captures the vast landscape of Big Sky, featuring a prominent mountain in the background. The scene showcases a blend of natural greenery and developed areas, with buildings and roads interspersed among the trees, highlighting the accessibility of outdoor activities.

4.93 out of 5 average rating, 167 reviews

Fresh Summer Air | 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.

ValueFamilyKitchen

5.0 out of 5 average rating, 29 reviews

The spacious living area features large windows offering mountain views, complemented by a stone fireplace and a mounted television. A cozy sectional sofa is arranged around a wooden coffee table, with modern armchairs nearby, creating an inviting environment for relaxation.

Home in Big Sky

4 Wildwood/ Ski in/Ski out

With premium ski- in/ski-out access right at your doorstep to the stagecoach lift, snowy adventures are just a step away. This exquisite 4- bedroom dwelling boasts a bonus room, fitted with two bunk beds, making it an ideal set the perfect ambiance with the in-house Sonos system and let your favorite tunes accompany you as you whip up delicious meals in the lavishly equipped kitchen. Here, culinary enthusiasts will find every gadget they could dream of.

LocationFamilyLayout

4.97 out of 5 average rating, 110 reviews

The exterior of a spacious wooden house is displayed under a layer of snow, featuring a large deck with railings. A prominent stone chimney is seen at one end, while the surrounding landscape is covered in a soft, white blanket of snow.

Guest suite in Big Sky

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

ValueLocationDecor

4.81 out of 5 average rating, 175 reviews

Ski Bunny Studio | Steps to Ski Lifts

Welcome to Ski Bunny, your cozy Big Sky ski retreat! Located in the Hill Condos, this sunny studio offers south-facing windows, mountain views, and easy slope access. Walk to the lifts, return for lunch, and unwind as the sun sets behind Andesite Mountain. Enjoy local charm, nearby dining, groceries, and the free Skyline bus only a 2 minute walk. Once you arrive, you can ski, eat, sleep, and repeat—no car needed!

FamilyLocationAccuracy

5.0 out of 5 average rating, 18 reviews

Home in Big Sky

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.

FamilyLocationSkiing

Superhost

The exterior of the condo is showcased in a serene winter setting. Snow covers the ground and the evergreen trees frame the building. The two-car garage is visible, and large windows reflect the evening sky with hues of pink and orange.