Giddy Up, Partner


Happy Trails has been transformed from a small horse ranch in the Montana mountains into a luxurious western vacation home. Located in Big Sky, Montana, Happy Trails is an exclusive vacation home now being offered as the perfect getaway for your family reunion or large group vacation. 

Happy Trails sits on 22 private acres and boast 7 bedrooms and 8 bathrooms. This compound features a large main house, a new guest house, and a huge party barn. Perfect for your group to have the space to spread out, or come together for storytelling and s'mores around the campfire. The property's location is one of its best features. It's only 50 minutes from Yellowstone National Park, a few miles from Big Sky Ski Resort, and minutes from the restaurants and shops of Big Sky Town Center. Close to everything yet perfectly private gives you the best of both worlds.  


5,800+ sq. ft. of  Living Space     2,000+ sq. ft. Party Barn


Pure Montana Living


*WARNING: Once you've vacationed at Happy Trails, you may never want to leave. The rustic log cabin main house spans more than 4,380 sq ft.  Upon entering you are greeted with a 20 ft tall, double-sided wood burning fireplace that separates the entry and main living area. On this main floor you will find a master ensuite with fireplace, the living area, kitchen, dining room, sunroom, laundry room, and an expansive deck overlooking the acres of tall pines. All furnished in luxurious Montana decor. The huge bunk room sleeps 4, with its own tv area featuring a large screen TV, Xbox, couch, chairs, and fireplace. Great for the kiddos to have their own space. Down the hall sits another master suite with fireplace and ensuite. This suite had a king bed and a twin day bed with a trundle, making this room the perfect place for a couple with young kids. Both downstairs rooms open to the expansive back yard, large jacuzzi, and acres of private land.

SLEEPS 10 (2 king beds, 1 twin daybed, 1 twin trundle, 4 bunk twins)


Cowboy Chic


The newly constructed guest house sits across the gravel driveway from the main house and above the Party Barn. Featuring high ceilings and rustic furnishings, the guest house is no slouch to the main house. The views from here are nothing short of spectacular. The front of the house opens to a mud room surrounded by windows, a living room, kitchen with modern appliances, and a dining area. Down the hall are the three bedrooms, bath, and full laundry room. The first bedroom, named the "Wildflower Room", features a king bed and sitting area. It shares a common full bath with the adjacent "Cowboy Room". This room features 2 twin beds with head boards made from old barn doors. The master suite, or "Ski Room", spans the width of the house and features a king bed and en suite.

 GUEST HOUSE SLEEPS 6 (2 king beds, 2 twins)



No Horsing Around


We've sent the horses on their own vacation and cleared out the new barn to make space for a dream game room. Open the barn doors, and be treated to amazing mountain breezes. You will find something for everyone in the Party Barn. Choose from watching an old western movie on the flat screen TV, a game of darts, playing cards, playing pool, playing shuffle board, or competing for the king of the mountain ping pong championship.  

For an adventurous pair, we have converted the tack room into a bonus bedroom. It features 2 twin beds, a closet, and a 15 ft ceiling. It sits in the front corner of the barn next to a half bath. This bedroom and bath are heated year long, but please note the barn itself is not heated.




3D Interactive Tour


Winter Wonderland


Winter activities abound in Big Sky. Trust us and resist the temptation to ski every day, and instead explore all that winter has to offer. Below are just a few of our favorite winter activities. 

The beauty of this place is so serene and majestic when covered in a blanket of pure white snow. Whether you like to go fast and be adventurous or want to slow down your pace, there is something for everyone this winter at Happy Trails.



Downhill Ski

Biggest Skiing in America

5,800 acres, 300 named runs on 4 connected mountains make Big Sky Resort the biggest skiable acreage in America. Snow enthusiasts come to leave crowds and traffic behind, lapping ski runs with hardly a wait. The Resort is consistently recognized in national ski magazines for short or nonexistent lines even during peak times and holidays. Varying terrain provides fun for all levels of skiing ability.

X-Country Ski


The North Fork Trail -steps from our back door- is just part of the 85 groomed kilometers of nationally ranked cross-country ski trails maintained by our neighbor, Lone Mountain Ranch. How about snowshoeing? Yes, please! Trails also meander around our property. So accessible, so easy.


Dog Sledding

mush! mush!

Now this is something you will never forget. Bundle up and hang on, you are in for quite a ride. Experiencing a dog sled ride zooming through the snow-covered pines is nothing short of exhilarating.

Snowmobile at YNP

Experience the park in winter

Starting just outside the park in West Yellowstone, climb onto a powerful snow machine and be guided through Yellowstone to reach Old Faithful. Between the heated seats and spectacular views, you hardly notice the winter weather.


Sleigh Rides

Snow Shoe

Summer Adventures


So much to do, so little time to do it. But with sunset as late as 9:30 pm in the summer, you'll have more time than usual. There just isn't anything like Montana in the summer. From hiking, to fly-fishing, to mountain biking and horseback riding, to...well the list just goes on and on. Below are just a few of our favorite summer activities. We are happy to provide you with recommendations for all activities. (sample itinerary here) 


Word Class Hikes

Take a Hike

Some of the best hiking is just outside your back door. The North Fork trailhead borders our property and offers plenty of hiking options. Three of the top ranking hikes in Montana are just a few miles away. (Ousel Falls Hike, Beehive Basin Hike, Laval Lake Hike)


Go Fish

Anglers from all over the world head to the rivers surrounding Big Sky, Montana. The blue ribbon rivers include: Madison, Gallatin, Yellowstone, Big Hole, and Missouri.


Mountain Biking

Whitewater Rafting


Horseback Riding

Cowboy Cookout

Bridge Jumping

Yellowstone National Park


Basecamp at Big Sky Resort


Frequently Asked Questions

What is the maximum number of guests? 

During the winter Happy Trails can accommodate 16 guests- 10 in the main house and 6 in the guest house.

During the summer we can accommodate 18 guests (same as above plus 2 in barn bedroom).

Where is the nearest airport to Big Sky?

Bozeman International Airport (BZN) is a beautiful 45-55 minute drive away. There are direct flights from many cities, including: Houston, Atlanta, Chicago, Denver, Minneapolis, Portland, Seattle, San Francisco, Los Angeles, Las Vegas, Phoenix, Salt Lake City, Newark, and New York La Guardia.

Should we be concerned about bears?

Bears are part of the beauty of Montana. You should be "bear aware" while hiking and enjoying the outdoors. The best defense against a bear attack on a hike is to bring a chatty hiker (bears are usually scared off by human voices). Bear spray should be carried with you on all hikes. 

How far is Yellowstone National Park?

The west entrance of the park is less than an hour's drive. As an eagle flies, the park itself is just 15 miles from Big Sky.

Below is a sample itinerary for a summer visit to Big Sky. Contact us for details and other activities.