Search Chalets in Southwest Montana

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 35 Chalets in Southwest Montana with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (119)
"the property had everything you would want and very comfortable for all 6 of us! I would recommend renting this property! "
The price is SAR 3,755
SAR 7,021 total
includes taxes & fees
20 Dec - 21 Dec
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!!

9.6 out of 10, Exceptional, (24)
"We absolutely loved this property-couldn’t ask for a better location! Convenient to everything -don’t ever need to leave the mountain, didn’t move the car one time! Perfect for extended family, great table for playing cards and board games. House is fully stocked - kitchen, games. The only thing missing is facial tissue. Only warning - all guests need to be quite mobile - the path to the condo can get snowy/icy. Loved being a stone’s throw away from The Cabin and Scissorbill’s Saloon! Great trip...
Totally Remodeled Arrowhead Chalet. Awesome location!! Ski in/ski out!!

New! Luxury 4 Bed Ski-In/Ski Out in Moonlight Basin

9.4 out of 10, Exceptional, (3)
"We lucked out and had a snowstorm the day we arrived so it was definitely ski out. It took some exploring to figure out ski in but it was doable but slow until a day later when they groomed part of the path. The townhouse was hard to find in the dark, It is behind the first garage on the right when you get to the right road. The inside was very comfortable for 4 adults"
New! Luxury 4 Bed Ski-In/Ski Out in Moonlight Basin

Spacious and Remarkable Ski In-Ski Out Retreat

9.8 out of 10, Exceptional, (21)
"We had 3 families with kids stay together and it was great. A great space to all be together, but also place for everyone to retreat to when needed. Hot tub was great and easy access to a trail out the back door was super convenient. Would definitely stay again!"
Spacious and Remarkable Ski In-Ski Out Retreat

Big Sky Vacation Rentals: Homestead 14 Claim Jumper

9.8 out of 10, Exceptional, (7)
"Great Ski-In/Ski-Out location. Well-maintained and managed property. Ideal setting, great views."
Big Sky Vacation Rentals: Homestead 14 Claim Jumper

Stunning home near slopes with 3 decks, hot tub & 2 kitchens - dog-friendly

7.2 out of 10, Good, (9)
"This property was not very clean and there were several problems. The first problem was the property was under construction. There was nails, screws building material all over the driveway and porch to enter the house. Once in the house there were no towels, toilet paper"
Stunning home near slopes with 3 decks, hot tub & 2 kitchens - dog-friendly

Reboot, Recover, Recreate…Centrally located 20 acre Mill Creek getaway cabin!

10.0 out of 10, Exceptional, (11)
"A great place to stay"
The price is SAR 559
SAR 872 total
includes taxes & fees
26 Nov - 27 Nov
Reboot, Recover, Recreate…Centrally located 20 acre Mill Creek getaway cabin!

Big Sky Home, Spacious and Clean, with Private Hot Tub, Fireplace and Garage

9.8 out of 10, Exceptional, (43)
"Wonderful place to stay. Unit was clean and a perfect location near Big Sky."
Big Sky Home, Spacious and Clean, with Private Hot Tub, Fireplace and Garage

Ski In/Ski Out Updated Big Sky Retreat

9.8 out of 10, Exceptional, (13)
"The pictures on Vrbo look amazing but it looks even more amazing when step inside the house. The house was perfect in all aspects and had everything we needed for a group of 8 of us. The ski on was awesome and just a short walk to an actual trail that will take you to the base of the mountain, was very cool to ride through the trees with houses around us. We got a lot of snow during our stay so make sure you have all wheel drive cause the driveway is uphill"
Ski In/Ski Out Updated Big Sky Retreat

Yellowstone, Fly-fishing, Golf, Hiking & Biking

10.0 out of 10, Exceptional, (15)
"This house was a great fit for our family with 4 teenagers. Plenty of room to spread out and they loved the hot tub after long days skiing!"
Yellowstone, Fly-fishing, Golf, Hiking & Biking

Big Sky Vacation Rentals: Homestead 16 Claim Jumper

9.8 out of 10, Exceptional, (18)
"The place is absolutely beautiful and well laid out, everything was well stocked and very clean. The views from every window is stunning!"
Big Sky Vacation Rentals: Homestead 16 Claim Jumper

Big Sky Vacation Rentals: Homestead 4 Claim Jumper

9.8 out of 10, Exceptional, (12)
"We rented this property for a family vacation in Big Sky with 12 adults and a 4-year old. The house was perfect! Enough bedrooms for everyone to have their own room and space throughout that we didn't feel like we were on top of one another. Great location near Big Sky Resort too and close enough to town that you didn't feel like you were driving a lot. The view from the property was incredible too. Would definitely rent again!"
Big Sky Vacation Rentals: Homestead 4 Claim Jumper

Ousel Falls Retreat - Big Sky Town Center

10.0 out of 10, Exceptional, (1)
"The house is very nice, fully equipped and operational and just a short drive from the Slopes in the winter, perfect for a lovely stay!"
Ousel Falls Retreat - Big Sky Town Center

Stunning Big Sky Home with Incredible Views and Ski Access!

10.0 out of 10, Exceptional, (22)
"We stayed in the property for spring break- the house was a great setup for 2 families with 5 kids combined. The only tricky part was figuring out access to/from the house to the lifts and then back in the afternoon. Easy drive into town and great views from the house"
Stunning Big Sky Home with Incredible Views and Ski Access!

Big Sky Vacation Rentals: Homestead 12 Claim Jumper

9.2 out of 10, Wonderful, (9)
"The house is beautiful in a gorgeous setting with easy access to skiing. The space is very luxurious and the hot tub is private."
Big Sky Vacation Rentals: Homestead 12 Claim Jumper

Big Sky Vacation Rentals: Homestead 10 Claim Jumper

10.0 out of 10, Exceptional, (17)
"Excellent home for a large family, great location, not far from ski lifts!!"
Big Sky Vacation Rentals: Homestead 10 Claim Jumper

Alpine Haus Philipsburg

9.4 out of 10, Exceptional, (43)
"When you walk in it’s a unique place but staying here you will really enjoy, it’s comfortable and has all you need to stay. Great location "
Alpine Haus Philipsburg

Big Sky Vacation Rentals: MMH 5 Derringer

10.0 out of 10, Exceptional, (16)
"We loved the privacy, scenic views and spacious home!! We had a wedding at the Yellowstone Club so didn’t realize we would be so far up and down and up the mountain but it all worked out!! Easy drive into town!! Loved the hot jacuzzi waiting for us when we woke up the next morning!!"
Big Sky Vacation Rentals: MMH 5 Derringer

Anaconda Chalet - Ski Discovery, Golfing, Fishing, Mountains and incredible view

9.8 out of 10, Exceptional, (28)
"Lots of room, clean, great view. "
Anaconda Chalet - Ski Discovery, Golfing, Fishing, Mountains and incredible view

Big Sky Vacation Rentals: Homestead 6 Claim Jumper

10.0 out of 10, Exceptional, (30)
"This property was exactly as advertised. The views were magnificent. The furnishings, fabrics, kitchen supplies were very high quality. The instructions for use of all appliances etc were clear and easy to find. The keyless entry was also a breeze to handle. We would happily return and recommend this home to any one!"
Big Sky Vacation Rentals: Homestead 6 Claim Jumper
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.
Don't see what you're looking for?
See all available properties in Southwest Montana
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Southwest Montana

Condo walking distance to lifts/Mountain Village

8.4 out of 10, Very Good, (25)
"Nice unit in Big Sky. We traveled to Yellowstone."
The price is SAR 939
SAR 1,746 total
includes taxes & fees
30 Nov - 1 Dec
Condo walking distance to lifts/Mountain Village

Holiday Availability! One-of-a-Kind Home with Incredible Views on 60-Acre Property with Hot Tub

9.0 out of 10, Wonderful, (12)
"We loved our stay at Lone Peak View. The 360-degree mountain views are absolutely incredible and we loved sitting up in the living room watching the sunrises & sunsets. The hot tub is nice and big and it was cleaned well. The WiFi and LTE speeds were slow but adequate for a vacation (just keep that in mind if you're working remotely). In winter you definitely need a 4WD or AWD vehicle with snow tires. We wouldn't have been able to get up the driveway without snow tires. Keep in mind that the...
Holiday Availability! One-of-a-Kind Home with Incredible Views on 60-Acre Property with Hot Tub

Sugar Loaf Lodge & Cabins

2.0 star property
9.0 out of 10, Wonderful, (116)
"This place is wonderful! We will be back!"
The price is SAR 469
SAR 507 total
includes taxes & fees
23 Nov - 24 Nov
Sugar Loaf Lodge & Cabins
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.