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

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Top-rated ski-in/ski-out rentals in Madison County

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Guest favorite

A comfortable seating area is visible, featuring a brown sofa adorned with decorative cushions and a blue accent chair. Two round wooden tables are positioned close by, and natural light filters through the large windows, offering views of the surrounding trees.

Condo in Big Sky

4.89 out of 5 average rating, 184 reviews

Moose Tracks Condo in Big Sky Resort

Welcome! Moose Tracks Condo is your home away from home for mtn fun. Fully equipped studio to enjoy playing at and working from Big Sky Resort. A 12-minute walk or free shuttle ride to the base. Free area bus just steps away. Includes free parking plus a full kitchen. A big window overlooks the stream and woods out back. World class skiing, mountain biking, blue ribbon fly fishing, hiking and even a small lake for paddling in summer. Only 45 minutes to West Yellowstone and the National Park.

Top guest favorite

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.

Condo in Big Sky

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.

Guest favorite

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

5 out of 5 average rating, 6 reviews

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.

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.

Condo in Big Sky

4.92 out of 5 average rating, 181 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.

Guest favorite

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.

Condo in Big Sky

4.92 out of 5 average rating, 158 reviews

*3 Level Loft *Lone Peak Views* Shuttle to Lift

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 • Great for Couples or Small Groups

Top guest favorite

A functional entryway is featured, showcasing a built-in storage area for ski gear. Colorful skis are mounted on the wall, with ski boots stored below. Modern cabinetry lines the kitchen area, which is equipped with stainless steel appliances and fixtures.

Apartment in Big Sky

5 out of 5 average rating, 81 reviews

Beautiful, remodeled condo. Prime ski 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

Guest favorite

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.

Condo in Big Sky

4.91 out of 5 average rating, 116 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.

Superhost

A cozy studio space is highlighted by gold-flaked mirror walls and retro furnishings. A patterned sofa faces a coffee table, with bright natural light streaming through large windows. Green plants add a touch of nature, while vintage lamps provide soft illumination.

Condo in Big Sky

4.8 out of 5 average rating, 194 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.

Superhost

A stylish, colorful living space features a spacious bed with decorative pillows. Surrounded by vibrant walls, a cozy seating area includes a colorful chair and lamp. Natural light streams through large windows covered with light fabric, highlighting the tasteful decor and scenic wall art.

Condo in Big Sky

4.79 out of 5 average rating, 102 reviews

Cozy, Large, Colorful 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.

Guest favorite

A serene sleeping area features a spacious bed with white linens and a grey throw blanket. Nightstands with lamps flank the bed, while a large mirror reflects the room's calming green wall. An abstract art piece adds visual interest to the space.

Apartment in Big Sky

4.89 out of 5 average rating, 135 reviews

Studio getaway within walking distance to ski lift

Enjoy your time in Big Sky in this top floor studio apartment!! 8:00am check in, 4:00pm check out! This home is located walking distance to Big Sky Ski Resort and has an incredible view of the iconic Lone Peak from the window! It is a perfect spot for travel partners to come stay and enjoy the Biggest Skiing in America. This will provide you with everything you need to make your mountain getaway relaxing and fun.

Guest favorite

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.

Condo in Big Sky

4.9 out of 5 average rating, 241 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!

Superhost

A comfortable living area is furnished with a dark couch and a decorative pillow. A large artwork depicting a skier is displayed above a wooden shelf. Natural light floods through the expansive window, showcasing a snowy landscape outside.

Condo in Big Sky

4.8 out of 5 average rating, 161 reviews

Ski Bunny Studio / Walkable to Ski Lifts

This is the perfect ski getaway location! In the Hill Condos, right in the Big Sky Mountain area, this studio has everything you need to make your winter getaway comfy and cozy. Walk to the slopes in the morning, stop back in to make yourself lunch, and after the lifts close, watch as the sun sets behind Andesite mountain. Ski, rest, repeat.