Chalets in Madison County

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Madison County chalets

4 Bedroom Ski-In-Ski-Out Big Sky Cabin

4 Bedroom Ski-In-Ski-Out Big Sky Cabin
Powder Ridge
9.8 out of 10, Exceptional, (15 reviews)
"Great place for our group to enjoy some preseason training. Thank you. "
United States
Isabel G.
4 Bedroom Ski-In-Ski-Out Big Sky Cabin

Moonlight Magic! Best Views In Big Sky! True Ski-In/Ski-Out! Heated Ski Room!

Moonlight Magic! Best Views In Big Sky! True Ski-In/Ski-Out! Heated Ski Room!
Big Sky
10.0 out of 10, Exceptional, (153 reviews)
"Beautiful views"
United States
Dale S.
Moonlight Magic! Best Views In Big Sky! True Ski-In/Ski-Out! Heated Ski Room!

Totally Remodeled Arrowhead Chalet. Awesome location!! Ski in/ski out!!

Totally Remodeled Arrowhead Chalet. Awesome location!! Ski in/ski out!!
Big Sky Mountain Village
9.8 out of 10, Exceptional, (37 reviews)
"Great location, clean and had everything you need. "
United States
Gary O.
Totally Remodeled Arrowhead Chalet. Awesome location!! Ski in/ski out!!

Casa Big Sky - Two Bed Apt in Large Private Home on Groomed Ski Trail

Casa Big Sky - Two Bed Apt in Large Private Home on Groomed Ski Trail
Big Sky
9.8 out of 10, Exceptional, (95 reviews)
"Amazing views and comfortable space for a ski vacation."
United States
Erin B.
Casa Big Sky - Two Bed Apt in Large Private Home on Groomed Ski Trail

*New Listing* Ski-In/Ski-Out Chalet w/ Private Hot Tub

*New Listing* Ski-In/Ski-Out Chalet w/ Private Hot Tub
Saddle Ridge
10.0 out of 10, Exceptional, (2 reviews)
"The best ski in ski out condo I have rented at Big Sky. Been here 4 times but not at this condo. Amenities were perfect. Location was perfect. Very lucky that we found this gem!!!!!! Thank you so much. "
United States
Ben C.
*New Listing* Ski-In/Ski-Out Chalet w/ Private Hot Tub

Spacious Ski-In/Ski-Out Retreat

Spacious Ski-In/Ski-Out Retreat
Big Sky
9.8 out of 10, Exceptional, (29 reviews)
"It was such an amazing stay! Great location and loved that it was ski in/ski out. Everything we needed was there and the place was beautiful. "
United States
Nancy L.
Spacious Ski-In/Ski-Out Retreat

Big Sky Vacation Rentals: AM 5 Silver Star

Big Sky Vacation Rentals: AM 5 Silver Star
Big Sky
9.8 out of 10, Exceptional, (17 reviews)
"perfect mountain location with great chalet character"
United States
James C F.
Big Sky Vacation Rentals: AM 5 Silver Star

Big Sky Vacation Rentals: MMH 6 Harvest Moon

Big Sky Vacation Rentals: MMH 6 Harvest Moon
Big Sky
10.0 out of 10, Exceptional, (39 reviews)
"We will stay here again with family!"
United States
Denise J.
Big Sky Vacation Rentals: MMH 6 Harvest Moon

Ski-In/Ski-Out Big Sky Home with Incredible Views

Ski-In/Ski-Out Big Sky Home with Incredible Views
Big Sky
10.0 out of 10, Exceptional, (27 reviews)
"Beautiful setting!Lovely home has all you need for a fun family getaway!"
United States
Anonymous traveller
Ski-In/Ski-Out Big Sky Home with Incredible Views

Stunning Ski-In/Ski-Out Mountain Chalet

Stunning Ski-In/Ski-Out Mountain Chalet
Big Sky Mountain Village
10.0 out of 10, Exceptional, (2 reviews)
"I can't recommend this condo and the management group enough. The condo is stocked with everything you need, and is extremely comfortable. The location is awesome and it is a true ski in ski out. If you have a concern the management group responds almost immediately! Thank you for an amazing stay, we will be back!"
United States
Deidre F.
Stunning Ski-In/Ski-Out Mountain Chalet

Luxury Big Sky Ski Retreat - Moonlight Basin

Luxury Big Sky Ski Retreat - Moonlight Basin
Big Sky
10.0 out of 10, Exceptional, (6 reviews)
"Perfect location! Beautiful property. Would definitely stay here again. "
United States
Jason W.
Luxury Big Sky Ski Retreat - Moonlight Basin

*New to Market* Beautiful 4 Bedroom Ski In/Out Big Sky Home

*New to Market* Beautiful 4 Bedroom Ski In/Out Big Sky Home
Big Sky
8.0 out of 10, Very good, (1 review)
"The house is lovely and was stocked with everything you need. It was clean and comfortable for our group of 7 and could have fit a couple more kid easily. The new property manager was friendly and responsive. All was great except 2 things- 1 the wood burning fireplace is not usable which was a big bummer because we really wanted to relax to a fire/make smores after skiing. Property manager was responsive and tried to help but there’s something wrong with the air flow. Even for the manager...
United States
Jennifer K.
*New to Market* Beautiful 4 Bedroom Ski In/Out Big Sky Home

Luxurious Black Eagle Chalet

Luxurious Black Eagle Chalet
Big Sky Mountain Village
10.0 out of 10, Exceptional, (7 reviews)
"Great location, nice accommodations. We enjoyed our stay"
United States
Tim S.
Luxurious Black Eagle Chalet

Big Sky Vacation Rentals: Homestead 16 Claim Jumper

Big Sky Vacation Rentals: Homestead 16 Claim Jumper
Powder Ridge
9.6 out of 10, Exceptional, (26 reviews)
"Loved the location, rooms, Direct TV and hot rub"
United States
George Z.
Big Sky Vacation Rentals: Homestead 16 Claim Jumper

Big Sky Vacation Rentals: Homestead 8 Claim Jumper

Big Sky Vacation Rentals: Homestead 8 Claim Jumper
Powder Ridge
9.4 out of 10, Exceptional, (15 reviews)
"Great property with all the amenities for a group retreat! Enjoyed fire pit at night and hot tub. Kitchen was perfect for group cooking and all items needed for food prep were there. Easy access to shops and Farmer's Market in Big Sky. Definitely a place to return to!"
United States
Kathy Z.
Big Sky Vacation Rentals: Homestead 8 Claim Jumper

Big Sky Vacation Rentals: Homestead 4 Claim Jumper

Big Sky Vacation Rentals: Homestead 4 Claim Jumper
Powder Ridge
9.6 out of 10, Exceptional, (13 reviews)
"Lovely home! We had a great time."
United States
Vandy F.
Big Sky Vacation Rentals: Homestead 4 Claim Jumper

Prime Ski-In/ Ski-Out Big Sky Powder Ridge Cabin

Prime Ski-In/ Ski-Out Big Sky Powder Ridge Cabin
Powder Ridge
Prime Ski-In/ Ski-Out Big Sky Powder Ridge Cabin

Big Sky Vacation Rentals: Homestead 12 Claim Jumper

Big Sky Vacation Rentals: Homestead 12 Claim Jumper
Powder Ridge
9.2 out of 10, Wonderful, (10 reviews)
"Great house. Really enjoyed our time."
United States
Brandon C.
Big Sky Vacation Rentals: Homestead 12 Claim Jumper

Big Sky Vacation Rentals: Homestead 10 Claim Jumper

Big Sky Vacation Rentals: Homestead 10 Claim Jumper
Powder Ridge
10.0 out of 10, Exceptional, (21 reviews)
"The house was wonderful for our large family to be together in Big Sky!"
United States
Stephanie C.
Big Sky Vacation Rentals: Homestead 10 Claim Jumper

New to Market! Vast Ski In/Ski Out Big Sky Chalet

New to Market! Vast Ski In/Ski Out Big Sky Chalet
Spanish Peaks
10.0 out of 10, Exceptional, (1 review)
"Excellent accommodations all around! We had an amazing stay here and will be back. "
United States
Sterling H.
New to Market! Vast Ski In/Ski Out Big Sky Chalet
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Madison County Hotel Reviews

Find out more about Madison County

Madison County Chalets information

Number of reviews
490
Accommodation
46 Chalets
Lowest Price
Highest Price

Explore a world of travel with Expedia