Ski-in/Ski-out vacation 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.

4.94 out of 5 average rating, 160 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 cozy living area features a brown leather sectional sofa adorned with patterned throw pillows. Natural light enters through windows showcasing a snowy forest view. A wooden dining table is visible in the background, complemented by rustic decor and wooden accents, enhancing the warm ambiance.

4.79 out of 5 average rating, 34 reviews

Cozy ski-in/out home w/fireplace & clawfoot tub

Little Plume Flat is the quintessential cozy, ski-in/ski-out flat! This luxury above garage flat is awaiting you for your next Big Sky Escape! Delight in this winter wonderland escape and warm up by the cozy stone fireplace. Have a bubble bath in the vintage clawfoot tub and watch as the snow falls. Cook up a gourmet meal in the gorgeous kitchen and serve it up at the adorable 4-person dining table right next to the fireplace! The owner lives on-site in the main house attached to the garage.

4.78 out of 5 average rating, 9 reviews

A secluded retreat is nestled in a snowy landscape, surrounded by tall evergreen trees. Soft lights illuminate the structure, highlighting the modern architecture against the dusk sky. The mountainous terrain in the background adds to the serene, remote atmosphere.

Home in Big Sky

True Montana Experience: Secluded & Unreal Views!

Welcome to Backcountry Lookout, a secluded one-bedroom hideaway on a 9,000 ft ridge overlooking Beehive Basin. Enjoy stunning views of Lone Peak, The Sphinx, and Fan Mountain through floor-to-ceiling windows. Wake up to unforgettable sunrises and starry nights, with the chance to see the Northern Lights. Surrounded by national forest, this cozy retreat offers peace, wildlife sightings, and direct access to Big Sky’s best backcountry skiing. A true Montana gem for nature and adventure lovers.

4.94 out of 5 average rating, 69 reviews

The exterior view captures a multi-level condo with a dark roof, set against a backdrop of trees and mountains. The structure is surrounded by greenery, and a clear sky is visible above, highlighting the peaceful natural setting.

Apartment in Big Sky

St. Moritz in Big Sky

Efficient, clean, tile flooring throughout, 1 sm bdrm queen/1 murphy double bed condo at mountain village at the lifts. 440 sq ft. bright S+W facing 2nd level end unit w/ porch facing mtn. Takes me 12 minutes slight uphill to walk to lifts or shorter w/shuttle. HS internet/UHD smart TV/HULU+Live TV. NO DOGS or pets. Sofa,charging strips,boot heaters,ski rack,wall hooks,pancake mix, coffee. View of mtns+woods. Shared porch w/Lone Peak view. Small shower and combi washer. 2 adults+1 child max.

Top guest favorite

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.

4.93 out of 5 average rating, 188 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.

4.86 out of 5 average rating, 121 reviews

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.

Home in Big Sky

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.

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.

4.93 out of 5 average rating, 162 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

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.

4.92 out of 5 average rating, 128 reviews

Tranquil 2BR Retreat | Ski In Ski Out

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.

The cozy studio living area features a patterned sofa, surrounded by lush plants and a gold-flaked mirror wall. A wooden coffee table anchors the space, while artwork on the walls adds a touch of character. Natural light streams in through large windows, enhancing the inviting atmosphere.

4.81 out of 5 average rating, 197 reviews

Innsbruck 1974 | Walkable to Big Sky Resort

Stay in a 70s time-capsule in the heart of Big Sky, Montana with views of Lone Peak! Innsbruck is best for those looking for an immersion into local mountain life. With trails right out the door and at the foot of Big Sky Resort, this cozy studio couldn't be in a better location. The complex is shared with locals who ride bikes, run, hike, and ski on the trails you are going to want to be on! Basecamp here for your Big Sky / Yellowstone adventure.

A cozy living area is highlighted by a large sectional sofa and a rustic coffee table. Brightly colored walls frame a window that allows natural light in, and a smart TV is mounted above a stone fireplace. Comfortable seating features a mix of textures and patterns.

4.79 out of 5 average rating, 102 reviews

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.

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.

4.9 out of 5 average rating, 242 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!

The bedroom features a spacious bed dressed in crisp white linens. A decorative rug lies beneath, adding warmth. Natural light enters through two windows, with light curtains softly diffusing the sunlight. A ceiling fan is present, and minimalist bedside tables hold elegant lamps.