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

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, 168 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.

A welcoming living area features a comfortable red sofa with a 'SKI' pillow and a cozy orange armchair. A wooden coffee table is placed in front, while a wall-mounted TV and bright window provide light. Ski equipment is displayed on the wall, adding a playful touch.

4.86 out of 5 average rating, 126 reviews

Located at Ski Resort | On Ski Shuttle Route

*MAX OCCUPANCY 2 ADULTS & 2 CHILDREN This 1BR + Murphy Bedroom Condo is perfect for couples or small families looking for the best location right on Lone Mountain! Updated, new bedding, and very cozy! Walk to the lifts or take the shuttle to Mountain Village, right from your front door! This cozy retreat offers comfort and convenience. Enjoy scenic views, a fully equipped kitchen, great location right at the base of Lone Mountain. With easy parking, explore Big Sky's charm and adventure.

Superhost

A cozy living area features a sectional sofa adorned with decorative pillows, positioned near a window offering views of the surrounding landscape. A small table sits on a light-colored rug, while a staircase leads to the upper levels, providing access to additional living spaces.

4.91 out of 5 average rating, 173 reviews

*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

Superhost

An outdoor deck features a private hot tub with bubbling water, surrounded by scenic mountain views. A rustic wooden ceiling and log framework provide structure, while wooden rocking chairs are positioned nearby. A panoramic landscape of trees and distant peaks under a partly cloudy sky is visible.

4.9 out of 5 average rating, 20 reviews

Ski-in/Ski-out w hot tub/ in Moonlight Basin

Enjoy a true out West vacation in this ski-in/ski-out "Wild West" Cowboy Heaven Cabin. With the back drop of Lone Peak and panoramic views of the Big Sky valley, the sunrise and sunset will take your breath away. This cabin offers easy ski-in/ski-out to the Powder River ski run, which sits on the ridge joining Big Sky to Moonlight Basin. Enjoy your private outdoor hot tub and outdoor seating to take in the amazing views. You will feel as though you are literally on top of the world.

Top guest favourite

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.

Flat in Big Sky

5 out of 5 average rating, 105 reviews

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

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.

4.77 out of 5 average rating, 105 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!

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, 146 reviews

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.

Top guest favourite

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

4.97 out of 5 average rating, 103 reviews

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

Superhost

5 out of 5 average rating, 4 reviews

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.

A large window is framed by light-colored curtains, offering a view of snow-capped mountains and evergreen trees. The bright sky provides a backdrop to the scene, enhancing the natural beauty visible from inside the studio.

4.89 out of 5 average rating, 247 reviews

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!

A rustic cabin with log siding sits against a colorful sunset sky. Large windows reflect the vibrant hues, while snow blankets the ground surrounding the structure. A pine tree is visible in the foreground, contributing to the mountain backdrop.

4.92 out of 5 average rating, 63 reviews

Cozy Ski-In & Ski-Out Cabin|Hot Tub|Stunning Views

Welcome to Cowboy Heaven 3, with unparalleled views and ski access. A dream for anyone wanting a true Montana experience! Aptly in the Cowboy Heaven community, enjoy the sweeping mountain views, private hot tub, and wood burning stove for a complete mountain-top oasis.

Top guest favourite

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.