Chalet holiday rentals in Madison County

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Top-rated chalet rentals in Madison County

Guests agree: These chalets are highly rated for location, cleanliness and more.

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Superhost
Chalet in Big Sky
5 out of 5 average rating, 3 reviews

Ski-in/Ski-Out Condo Private Hot Tub Moonlight

This Ski-In Ski-Out, 3 bed 2.5 bath townhome featuring a private hot tub in Big Sky, MT is your perfect winter getaway! This rustic getaway is steps away from the Iron Horse lift at Big Sky resort with unbeatable views of Lone Peak. Inside you are greeted by a cozy atmosphere with a open concept kitchen and living room. The kitchen features stainless steel appliances with everything you need to make a meal for the whole crew. The living room features a gray stone fireplace and easy access to t

Superhost
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.
Chalet in Big Sky
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.

Guest favourite
Chalet in Big Sky
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.

Guest favourite
Chalet in Big Sky
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.

Superhost
Chalet in Big Sky
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.

Superhost
Chalet in Big Sky

Luxe Mountain Home | Lone Peak Views | Hot Tub

★ Welcome to Big Sky Bliss, a thoughtfully designed mountain retreat for families and group getaways seeking space, comfort, and unforgettable views. ★ Nestled on a scenic slope near Big Sky Resort in the heart of the Gallatin Mountains, this newly remodeled home offers unobstructed Lone Peak views, modern upgrades throughout, and plenty of room for everyone to gather, reconnect, or enjoy a peaceful mountain escape year-round.

Superhost
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.
Chalet in Big Sky
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

Superhost
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.
Chalet in Gallatin Gateway
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.

Guest favourite
Chalet in Big Sky
5 out of 5 average rating, 6 reviews

Vast Ski In/Ski Out Big Sky Chalet

Luxury Ski-in/Ski-out Retreat in Big Sky, Montana <br><br>Experience the ultimate mountain escape at this stunning 6-bedroom, 8-bathroom ski-in/ski-out home, nestled in the heart of Big Sky, Montana. Whether you're here to carve the slopes, unwind by the fire, or explore the breathtaking landscapes, this luxurious retreat is the perfect base for your adventure.

Top Guest favourite
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.

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.
Chalet in Big Sky
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.

Superhost
Chalet in Big Sky
4.86 out of 5 average rating, 7 reviews

Big Sky Vacation Rentals: MMH 44 Cowboy Heaven

Set on a sunny perch high in Cowboy Heaven overlooking the Spanish Peaks, this tasteful alpine home tucked in the woods offers a top Big Sky ski-in/ski-out location with direct access to the slopes from your back door.

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