
Family-friendly holiday rentals in Madison County
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Top-rated family-friendly rentals in Madison County
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J. R. Boyce house
Step back in time in this completely restored 1865 Traditional style home. No detail was overlooked in this labor of love restoration. Park the car and take advantage of the close proximity to all of Virginia City's attractions, including the library and play area for the kids just across the street. With a large yard as well as a deck to enjoy the Montana sunsets, use our house to make memories to last a lifetime. No pets allowed in the house. Kenneling available at Ol'Blue Boarding in Ennis.
4.99 out of 5 average rating, 151 reviews
Hardy Hill Cabin
Escape to this private, beautifully refinished historic cabin just 4 miles east of Sheridan. Nestled in the foothills with breathtaking mountain views, wide-open skies, and unforgettable Montana sunsets, it’s the perfect place to relax and unwind. Enjoy the convenience of self check-in with a private entrance/keypad door. Ideally located near rivers, streams, hiking trails, and mountain adventures, this cozy retreat offers the perfect balance of seclusion and easy access to outdoor recreation.
5.0 out of 5 average rating, 123 reviews
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.
4.99 out of 5 average rating, 199 reviews
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.
4.93 out of 5 average rating, 160 reviews
Tiny Sauna cabin on 5 acres
Unique living 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 bathe. I will occasionally be out of reception for period of time. Prior communication is required so I can have your phone number.
4.85 out of 5 average rating, 121 reviews
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!
4.9 out of 5 average rating, 213 reviews
Blue Pine Guesthouse MT
This unique getaway is just blocks from downtown Dillon. It’s one of a kind blue pine interior is gorgeous & spacious. The perfect place to enjoy Southwestern Montana from. Dillon offers world renowned fly fishing in the summer, ski slopes 45 minutes away at Maverick mountain in the winter. There’s also the famous Elkhorn hot springs to visit for a $5 day. Enjoy Beaverhead-Deerlodge national forest and Clark Canyon reservoir. Come decompress in this small Montana town surrounded by nature!
4.96 out of 5 average rating, 227 reviews
The Ranch Cottage Hideaway with Sauna!
This three bedroom three bath cottage is part of a Montana working ranch that sits where the original homesteaders once staked their claim. Nestled along the South Boulder River this location is a great jumping off point for all your Southwest Montana adventures. Relax in your own private sauna with the beautiful backdrop of the Tobacco Root Mountains. Only two hours from Yellowstone National Park, minutes away from Lewis and Clark Caverns, and 75 feet from your new favorite fishing hole.
4.95 out of 5 average rating, 200 reviews
Montana Getaway with mountain views
Enjoy a peaceful Montana getaway with views of the Madison Range. We are situated on three acres where there is the main house and a garage with a unit above that is our guest house. Our guest house features a full kitchen, everything you need to eat in, a great place to rest after exploring the area. We are 2.5 miles to town center where you can find unique shopping and dining, 14 miles to the historic Virginia City, 10 miles to Ennis Lake, and 74 miles to West Yellowstone.
4.99 out of 5 average rating, 191 reviews
LK Ranch Cabin with hot tub and private fishing.
This 640 sq. ft. cabin, located in Alder Mt, is nestled on our 80-acre working ranch. The ranch has been a part of our family for over 120 years. You will have seclusion and a great view. Guests are welcome to enjoy private fishing on our stretch of Clear Creek. The Ruby River public fishing access is also within walking distance. Fishing licenses are required. Historic Virginia City is only 10 miles to the east and The Ruby Reservoir is just southwest, about 6 miles away.
4.99 out of 5 average rating, 116 reviews
Baker's Place
This 3 bedroom, 2 twins and a recent upgrade to a new king bed in the main bedroom, one bath with como tub/shower. New kitchen leinium adds beauty to the dining area. This Mobile Home is clean and simple. It has a spacious fenced back yard for kids and dogs. There is a nice porch for enjoying the evenings. We are friendly and love people. We are normally available for questions or help. If you are looking for somewhere reasonable and comfortable to stay give us a try.
4.91 out of 5 average rating, 186 reviews
The Garden Haus
Charming historic log cottage, newly remodeled. Nestled in a rural agriculutural neighborhood, the old historic Ruby Town, with enclosed private backyard and garden. Connect with the natural world and inspire your artist within! Delight in the vintage details and history of the house: 1 king, two twins, and a large open studio space. Enjoy soaking in the vintage tub, dining in the enclosed porch, and eating straight from the garden!
4.96 out of 5 average rating, 111 reviewsPopular amenities for Madison County family-friendly rentals
Family-friendly home rentals with a hot tub

New modern house with unreal view of Lone Peak!!
4.92 out of 5 average rating, 229 reviews
Enchanting cabin in the the Tobacco Root Mountains
4.9 out of 5 average rating, 20 reviews
4 Wildwood/ Ski in/Ski out
5.0 out of 5 average rating, 29 reviews
Big Sky Fire Towers • Private Hot Tub & 360° Views
5.0 out of 5 average rating, 8 reviews
Vast Ski In/Ski Out Big Sky Chalet
5.0 out of 5 average rating, 7 reviews
Big Sky’s Beehive Basecamp
4.99 out of 5 average rating, 86 reviews
Cozy Ski-In & Ski-Out Cabin|Hot Tub|Stunning Views
4.93 out of 5 average rating, 71 reviews
Luxurious Ski-In/Ski-Out Retreat
4.98 out of 5 average rating, 59 reviewsFamily- and pet-friendly home rentals

Tiny house and RV hook-up in Big Sky Country
4.95 out of 5 average rating, 169 reviews
Fresh Summer Air | Close to Slopes
4.93 out of 5 average rating, 167 reviews
Countryside Bunkhouse near Madison River
4.98 out of 5 average rating, 110 reviews
Fully Equipped Large Family House In-Town Location
4.89 out of 5 average rating, 108 reviews
miners off grid cabin 2 bedroom 1 bath
5.0 out of 5 average rating, 17 reviews
The O-X House
4.96 out of 5 average rating, 27 reviews
Ennis (Cameron) Montana Cottage A with great views
4.8 out of 5 average rating, 69 reviews
Littlefoot Cabin - Ennis Cabin Getaway
4.97 out of 5 average rating, 76 reviewsFamily-friendly home rentals with a pool

Amazing Lone Peak Views, excellent location
4.89 out of 5 average rating, 100 reviews
Cozy get away for 2 overlooking Lone Mountain
4.97 out of 5 average rating, 110 reviews
Luxury Moonlight Basin 2 Bedroom Condo
4.78 out of 5 average rating, 27 reviews
Condo w/ hot tub, fireplace, great views & a gym!
4.9 out of 5 average rating, 20 reviews
Big Sky Vacation Rentals: Mountain Lake 101B
4.71 out of 5 average rating, 14 reviews
Madison Vista-Big Sky Shoshone Ski in/Out Condo
5.0 out of 5 average rating, 50 reviews
Big Sky 2BR Resort Condo and Base of Lone Mtn.
5.0 out of 5 average rating, 14 reviews
Resort Access | Community Amenities
4.67 out of 5 average rating, 6 reviewsDestinations to explore
- Luxury rentals Madison County
- Cabin rentals Madison County
- Rentals with a hot tub Madison County
- Chalet rentals Madison County
- Ski-in/ski-out rentals Madison County
- Flat rentals Madison County
- Pet-friendly rentals Madison County
- Apartment rentals Madison County
- Guest house rentals Madison County
- Rentals with lake access Madison County
- Townhouse rentals Madison County
- Family-friendly rentals Montana
- Family-friendly rentals United States





