Chalet vacation rentals in Madison County

A private hot tub is situated on a deck, offering views of the expansive mountainous landscape. Snow-covered peaks rise in the background, while trees frame the serene setting. Water bubbles gently within the tub, creating a relaxing atmosphere.

5 out of 5 average rating, 3 reviews

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

Ski-in/ski-out from this 3 bedroom/2.5 bathroom + bonus room Montana Mountain Chalet. Only steps away from the Iron Horse Lift and with your own private hot tub, this chalet offers all of the luxury and comfort that you could possibly want, with a true Montana rustic feel. This unit is equipped with a gas grill on the deck & a sled for afternoon fun and TV's throughout. You can watch your kids sled from your back deck as you soak in the hot tub with a delicious beverage of your choice.

LocationValueHot tub

4.83 out of 5 average rating, 6 reviews

New! Ski-in/ski-out condo w hot tub & grill

Welcome to The Snowline Chalet, a true ski-in/ski-out townhouse nestled in Big Sky’s Saddle Ridge community. This three-bedroom, two-and-a-half-bath home spans three levels, each offering sweeping valley views, multiple balconies, a private hot tub, and a grill. With true ski-in/ski-out access, guests can hit the slopes effortlessly via the nearby Iron Horse Lift—the preferred choice for quick access to Big Sky’s vast terrain. The Pony Express Lift also provides additional access.

LocationValueWalkability

5 out of 5 average rating, 9 reviews

Ski In, Slope Views, Private Hot Tub

Steps from the Iron Horse lift, Timber Wolf Chalet puts you slope-side at the biggest skiing in America. Ski in, drop your gear, and sink into the private hot tub with mountains staring back at you. Four bedrooms, 3.5 baths, and room for 10 spread across three levels. The great room has a gas fireplace and double decks made for morning coffee and après drinks. Kitchen is fully stocked, WiFi is fast, and the slopes are literally outside your door. This one books fast for a reason.

FamilyValueView

5 out of 5 average rating, 8 reviews

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

Ski-in/ski-out from this 2 bedroom/2.5 bathroom Saddle Ridge townhome. As you walk in, the main level opens to the kitchen, gas fireplace, dining area, and breakfast bar. Walk out on our deck to take in the views while cooking on our gas grill. Upstairs you will find the master suite with a king bed and private bath. As you make your way downstairs from the main entryway you will find bedroom suite number 2. This room contains a queen bed and a twin/twin bunk bed.

LocationValueCleanliness

A private hot tub is featured on a wooden deck, with steam rising from the water. In the background, snow-covered mountains are visible, illuminated by the sun. The serene atmosphere is accentuated by the surrounding trees and the distant snowy residences.

4.83 out of 5 average rating, 30 reviews

Ski-in/Out w/private hot tub & gorgeous views

Saddle Ridge Family Retreat is the perfect Big Sky ski-in/ski-out townhome! This well appointed 3 bedroom townhome is awaiting you for your next Big Sky Escape! Located within the Moonlight base area is the Saddle Ridge ski-in/ski-out townhouse complex and it is the perfect blend of convenience and value. After a day of adventure you can relax in the private hot tub and take in the amazing views of Big Sky Resort. Stay Montana

LocationFamilyLayout

A scenic view from the balcony showcases a snowy landscape, with mountain slopes in the distance. Sunlight filters through the clouds, illuminating the trees and ski lifts below. Wooden posts frame the image, highlighting the outdoor seating area on the deck.

5 out of 5 average rating, 8 reviews

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

Don't miss the rare, true ski-in/ski-out opportunity to stay only steps from the Iron Horse lift in The Iron Horse Haven Chalet, 2 bedroom Saddle Ridge that sits on the slope.This property literally sits on the slopes! We guarantee that if you stay in this unit, you will never need to carry your skis! Ski to the Iron Horse or Pony Express lift in seconds and take your pick, Big Sky or Moonlight Basin.

LocationAccessAmenities

Chalet in Gallatin Gateway

The chalet features a modern A-frame design with a distinctive brown exterior. Large windows provide ample natural light, and a covered entrance is visible from the front. Surrounding greenery adds to the serene mountain environment.

4.91 out of 5 average rating, 33 reviews

Big Sky Paradise - Arrowhead

One of the most amazing ski-in/ski-out locations in Big Sky. Our 4-bedroom, 4 bath, 3 level chalet at the base of Silverknife ski run has everything you need to comfortably accommodate 8 guests. There are no other ski-in/ski-out chalets with 3 ensuite bedrooms (private bathroom/ shower) and wood burning fireplaces in the living room this close to the ski lifts, at this price, with our views.

FamilyLocationSleep quality

Top guest favorite

A rustic lodge is showcased at dusk, with warm light glowing from large windows. The building is framed by lush green grass and trees, adding to its inviting presence. The gentle slope of the lawn leads up to the welcoming front porch.

Chalet in Dillon

4.99 out of 5 average rating, 88 reviews

Expedition Lodge

My place is close to great views, restaurants and dining, and family-friendly activities. You’ll love my place because of the location, the ambiance, and the outdoors space. My place is good for couples, business travelers, families (with kids), and big groups. The outdoor rock fireplace is a customer favorite, and the sunsets are photo worthy.

LocationFamilyBathroom

4.88 out of 5 average rating, 34 reviews

Big Sky Vacation Rentals: MMH 5 Derringer

Experience mountain living at its finest in this Big Sky home situated atop Cowboy Heaven on the Moonlight side of Lone Mountain. Big Sky Resort ski access doesn’t get better than this with America's Biggest Skiing right off your back deck! This home was recently renovated and has new furniture, paint and art, throughout.

LocationValueNearby

The exterior of the two-story chalet features a spacious patio with a dining table and chairs. A hot tub is positioned nearby, surrounded by a verdant lawn. Large windows in the upper floor allow for ample natural light, and the surrounding trees contribute to a serene setting.

4.75 out of 5 average rating, 36 reviews

2 Bed ski out Apt in Private Home

Luxurious ski in - out rental apartment in private ski lodge in Big Sky, Montana. Full home comforts. Groomed ski trails to the resort lifts. Located on a warm southern facing slope of the Big Sky ski area, with panoramic views.

LocationFamilyCheck-in

The chalet is nestled among towering pines, showcasing a warm wooden exterior. Large windows reflect the sunset glow, illuminating the spacious wrap-around deck. The surrounding landscape features gentle slopes and distant mountain views, creating a serene mountain retreat.

4.79 out of 5 average rating, 29 reviews

Silver Star Alpine Lodge | Ski-In/Out Chalet |

This luxurious Alpine Meadows ski chalet is perched high on the slopes of Moonlight Mountain, secluded in a quiet cul de sac in the pines, with direct ski-in/ski-out to the uncrowded slopes of Big Sky Resort.

FamilyLocationAccess

The exterior of a spacious alpine home features a combination of wooden and stone elements. A large deck extends from the upper level, offering views of the snow-dusted landscape and surrounding mountains under a clear blue sky.