Family-friendly holiday rentals in Madison County

Vintage shotgun home with modern updates.

This vintage shot gun house retains its old-world charm while being updated with modern amenities. The bedroom area has a queen size adjustable bed. The living room area has a small sleeper sofa & a smart TV. The kitchen is full sized with a gas stove and stocked with basic cooking needs. The house faces the alley with 2 private parking spots and is located within walking distance of downtown Dillon, parks and U of MT Western. Fishing & hunting opportunities are within easy driving distance.

Moose Tracks Ski Condo in Big Sky Resort

Moose Tracks Ski Condo is a cozy retreat at Big Sky Resort. Great location for exploring, skiing, mountain biking, hiking, fly fishing the Big Sky area. A quick 12-minute walk or free ski shuttle to the base. Free area bus just steps away. Free parking plus a full kitchen. A big window overlooks a stream and woods. Easy access to world class skiing, mountain biking, blue ribbon fly fishing, hiking and a small lake for summer paddling. Only 45 minutes to West Yellowstone and the National Park.

Sunrise Silo - Luxury silo near Bozeman, Montana.

Newly constructed, 675 sq ft Sunrise Silo sleeps 4, with a queen bed in the loft and a main floor pull-out sleeper sofa. Sunrise Silo is a unique example of how rustic charm pairs perfectly with modern amenities and an indulgent experience. The stunning, unobstructed views of the Bridger Mountains and surrounding Gallatin Valley will ensure this becomes your favorite Montana vacation destination. Enjoy a rural setting while having easy access to adventure and entertainment opportunities.

2-bedroom Cabin in the Heart of the Ruby Valley

Bring your family for a vacation and enjoy some fishing in one of our Blue Ribbon trout streams including the Big Hole and Beaverhead Rivers less than a mile away… or maybe track down that monster bull this fall ... or come for a winter getaway and take a snow excursion in Yellowstone Park.... or just enjoy the peaceful views from our property and relax... the options are endless. This cabin has a full kitchen with dinnerware and utensils, full bathroom with full tub/shower and oil stove heat.

Cozy 2 Bedroom Condo Minutes from the Slopes

Cozy, first floor ski condo close to the mountain. Enjoy the privacy of two bedrooms, one with a queen bed and one with bunk beds. The kitchen is stocked with the basics. Hill Condos are convenient to the ski mountain, within walking distance of the conference center and Mountain Village with all of its amenities. The condo offers keyless entry, bluetooth stereo, and smart TVs, not to mention a beautiful view of Lone Mountain. It is 440 sq ft. and located less than a half a mile to the resort.

Dillon Den

Enjoy this private, charming 1 bedroom 1 bath unit that can sleep 4 guests. This stylish, comfortable suite offers all the amenities and extras along with a full kitchen, breakfast bar, and full bath. A fun theme helps give this unit its own character and style. A private parking area out front and a private entrance are part of this units attractions for guests to come and go with privacy. The bedroom offers a California King Mattress with high quality bedding for a great nights sleep!

Ruby Meadows Ranch Sheep Wagon

For the adventure traveler, try a night or two in a sheep wagon. Home on wheels to early sheep herders in the mountains of Montana, this hand built wagon sits on our 30 acre homestead. Finished under canvas with tongue and groove pine, this very small space offers a unique lodging experience. Inside is a nice queen size bed, 2 bench seats, and a pull out dining table. Enjoy mountain views from the outside bench, rocker & fire pit. Bathroom facilities in our nearby shop.

Cozy Slope-Side 2 Bedroom, Walk to Chairlifts!

Located at the base of Big Sky Resort, this cozy condo offers all the amenities you will need while away from home. It sleeps 7 comfortably offering 2 bedrooms (4 beds) and 2 full bathrooms. Includes a fully stocked kitchen, comfortable living space with fireplace, dining area, and communal coin-operated (quarters only) laundry area. The large private outdoor patio has a bistro set for your use. Only a one hour drive to Yellowstone Park via the West Yellowstone entrance!

Tiny Sauna cabin on 5 acres

Unique living experience with stunning mountain views and roaming pronghorn! Enjoy the quietness and feel like you are returning to the pioneer days. This is a fully functional house for two people. There is no running water into the house itself, but there is an electric well pump delivering water 200 yards from the house. There is an outhouse and a wood fired sauna to heat bathing water with. Drinking water, instructions and firewood are provided.

Ruby Valley Getaway Cabin

Welcome to our inviting and cozy studio cabin nestled in Twin Bridges, Montana, just a stone's throw away from the beautiful Beaverhead River. This picturesque cabin offers all the modern day luxuries while providing a quiet and serene setting to enjoy your time in the Ruby Valley. Whether you're here for a fishing expedition or a peaceful escape, our cabin is the ideal place to call home during your Montana adventure.

Countryside Bunkhouse near Madison River

Whether fishing, hunting, hiking, river adventures, or peace and quiet is what you are seeking, this is the perfect place for you! The bunkhouse is a newly built out studio apartment above our barn. Enjoy fresh eggs complimentary from our chickens (in the spring, summer, and fall months), bring your pets (as long as they are friendly with other animals). Enjoy fly fishing or tubing down the famous Madison River.

Madison Suite the Bluffs Best Views on the River

Singles and Couples will be delighted with this spacious and unique space. Private 950 Sq Ft fully appointed apartment with commanding views of the Madison River to the West, Madison Valley to the North and Madison Range to the East. Strong WiFi signal and desk space for remote working (if necessary). Walk in closet with clothes drawers and hangers for all your needs.