Chalet holiday rentals & accommodation in Madison County

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Top-rated chalet rentals in Madison County

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Chalet in Big Sky

4.86 out of 5 average rating, 7 reviews

Big Sky Vacation Rentals: MMH 7 Shadow Ridge

Get the most out of your Big Sky vacation when you stay in this sophisticated Moonlight Mountain rental home. Ideally located on the slopes in Cowboy Heaven, this stylish retreat boasts ski-in/ski-out access to Big Sky’s slopes from the back door! Professionally decorated, no detail has been overlooked in this chalet-style home. The great room features stylish rustic interiors with an artistic touch that makes the space warm and homey. Gather with friends in front of the wood fire with endless

13 – 20 May

$9,703 AUD total

Chalet in Big Sky

5.0 out of 5 average rating, 7 reviews

Big Sky Vacation Rentals: Homestead Chalet 4

It’s not easy to find a six-bedroom home in Big Sky and definitely not one as simply stunning as Chalet 4. This contemporary mountain home is perched on Lone Mountain in Big Sky Resort's newest and most sought-after development, with effortless access to the slopes. The best in Big Sky Lodging. This 3,500 sq ft trendy mountain home strikes the perfect balance between chic and alpine with modern interiors infused with warm wood finishes. Conveniently laid out over three levels, it allows for

28 Oct – 4 Nov

$10,245 AUD total

Guest favourite

Chalet in Big Sky

4.89 out of 5 average rating, 9 reviews

Big Sky Vacation Rentals: Homestead 8 Claim Jumper

Set amidst the pines in one of Big Sky’s most premier neighborhoods, this sleek modern mountain chalet is one of the few seven-bedroom vacation rental homes in Big Sky! A stunning retreat for large groups, family gatherings, and mountain getaways with friends. Chalet 8 features an impressive display of rustic mountain modern interiors and architecture with designer touches throughout. Expansive panes of glass truly bring the outdoors into this Big Sky rental home and with the crackling of the

7 – 14 Oct

$10,390 AUD total

Chalet in Big Sky

4.88 out of 5 average rating, 8 reviews

Big Sky Vacation Rentals: MMH 4 Shadow Ridge

*Currently the front deck for this home is undergoing renovations and will not be available until the summer of 2024. There will be no work taking place, but it will be unavailable. The hot tub is still available and has been relocated to the rear deck.* From its sunny perch up in Cowboy Heaven, this ski-in/ski-out chalet-style home is a mountain lover’s haven boasting amazing ski slope views and access to the slopes from your driveway! Luxurious alpine living, perfect views, and unmatched ski

25 July – 1 Aug

$10,208 AUD total

Chalet in Big Sky

5.0 out of 5 average rating, 3 reviews

Big Sky Vacation Rentals: Homestead 6 Claim Jumper

Homestead Chalet 6 is one of Big Sky’s largest and newest rentals in a premier neighborhood with excellent ski-in/ski-out access to the “Biggest Skiing in America”, Big Sky Resort. A contemporary interior design draws in the rustic elements of the rugged outdoors creating a true modern mountain living space that blends luxury, comfort and convenience. From the moment you enter this retreat, you are drawn to perfectly framed views of the evergreens from every angle. The great room offers a

24 – 31 May

$11,151 AUD total

Guest favourite

Chalet in Big Sky

4.81 out of 5 average rating, 42 reviews

Luxurious Black Eagle Chalet

Enjoy all the comforts of a western home and the wonderful open views of Lone Peak from this luxurious ski-in/ski-out Black Eagle Lodge condo. Nestled in a pine forest in the heart of the Big Sky Mountain Village, this quintessential mountain lodge is surrounded by natural splendor and privacy yet minutes from the activities, attractions and uncrowded slopes of Big Sky Resort. This creekside unit is located within walking distance to Lone Peak’s base area and its dining, shopping, .....

25 June – 2 July

$7,571 AUD total

Superhost

Chalet in Gallatin Gateway

4.88 out of 5 average rating, 16 reviews

Beautiful Big Sky Cabin Ski-in/out | Yellowstone

Relax in the outdoor hot tub breathing in fresh mountain air! This three-story, four-bedroom cabin sits in the shadow of Lone Mountain and the Spanish Peaks mountains. Ideal for a family vacation or holiday celebration. Hit the slopes in the winter with easy ski-in/ski-out access and easy access to hiking and biking trails, world class fly-fishing, golf, and majestic Montana weather in the summers.

9 – 16 Oct

$5,246 AUD total

Guest favourite

Chalet in Gallatin Gateway

4.9 out of 5 average rating, 21 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.

10 – 17 Oct

$7,900 AUD total

Guest favourite

Chalet in Dillon

4.99 out of 5 average rating, 74 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.

5 – 12 Jan

$4,330 AUD total

Chalet in Big Sky

5.0 out of 5 average rating, 5 reviews

Big Sky Vacation Rentals: AM 7 Silver Star

When it comes to Big Sky lodging, you can't beat Alpine Meadows! Sitting atop a perfect knoll in a quiet cul-de-sac in Moonlight Basin, this Silver Star chalet has grand views, direct ski-access and high-end amenities that make this an ideal Big Sky Resort vacation rental in any season.

4 – 11 Nov

$9,260 AUD total

Chalet in Big Sky

5.0 out of 5 average rating, 5 reviews

Big Sky Vacation Rentals: MMH 4 Mountain Home

If comfort and convenience are important to you on vacation, then look no further! This Moonlight Mountain gem is situated in Big Sky and Moonlight Basin's most sought-after location, Cowboy Heaven and you can ski right to/from the back door of the home.

18 – 25 Nov

$9,704 AUD total