House holiday rentals in Stillwater County

Big Sky Escape: Spacious Home on Working Ranch

The Ranch House 406 sits at the edge of a 50-acre pasture on a working ranch. Relax among rolling hills, spacious property and spectacular views of Montana's amazing wildlife. The large newly remodeled kitchen boasts brand new professional Thor kitchen appliances and the living room has vaulted ceilings, large windows overlooking the pasture and has an electric wood-burning stove. If grilling is your thing, fire up the stainless steel Nexgrill and enjoy the views and serenity of Big Sky Country.

Stephanie's Cottage

Stephanie’s Cottage is a charming and cozy house located just 1/2 block off the mainstreet, making it the perfect basecamp for your adventure. There are two queen bedrooms, providing the perfect space for a family of four or two couples traveling together. The clawfoot tub in the bathroom adds a touch of luxury to your stay. The living room and kitchen are cozy and well-equipped, giving you the option of staying in. And the best part? Your furry friend is welcome to join you on your adventure!

Ruby Red Retreat

Relax at this unique & tranquil getaway, less than 15 mi. to the start of the famous, breath-taking Beartooth Highway, considered the most scenic drive in America! Just 15 minutes to Red Lodge & 45 miles to Billings. Wake up to stunning views of the Beartooth Mountains from the oversize bedroom window and enjoy coffee on the covered front porch! Super comfy queen-size adjustable Tempurpedic mattress! 65" new Smart TV! Quiet, private country neighborhood, so please, no loud parties or noise.

Home of the Crazy Mountains and Boulder Valley

We are located less than a mile from the town of Big Timber in a private area overlooking a pond and a great view of the Crazy Mountains. Activities such as fishing the Yellowstone River or golfing at Overland Golf Course are just a hop, skip and jump away! The home itself is warm and inviting and has recently been upgraded with wonderful features. Whether you and your guests are ready to explore Big Timber and the surrounding areas or stay in for quality time, this home is perfect for you!

Rock Creek Paradise (Near Red Lodge, MT)

Described as "a little piece of heaven," this property is located on Rock Creek in Joliet, MT. Perfect for a family get-away - located 30 minutes from Billings and Red Lodge, MT, offering both city experiences and great outdoor activities. Fish out your back door on Rock Creek-both fly and reel enthusiasts love this creek. Ski in Red Lodge! Watch deer, turkey and other wildlife out your front window! Location is ideal for travel to Yellowstone Park, Custer Battlefield and Cody, WY.

The Bennett House

The Bennett House is easy to access as it's located just within the main entrance of our family owned and operated cattle ranch. To the east of the house is the iconic Yellowstone River, with the Bear Tooth and Absarokee Mountain Ranges in the far distance. To the west are the majestic Crazy Mountains. The Bennett House is just 3 miles from the Pelican fishing access, a great take-out/ put-in spot to the Yellowstone river. Be prepared to see lots of wildlife while you are here!

The Blue House on Broadway

My house is located right in Red Lodge, easy walking distance to shops and restaurants. The Ski Mountain is just 5 miles away. You will love Red Lodge! I don't charge a cleaning fee as I think that should be in the rental price - you can't opt out of cleaning!! I do just ask you to book in the correct number of guests that will be staying. I charge for any additional people over 2 which offsets the cleaning fee. There is only one bathroom so please take that onto account .

Long Stay Discount!

Ideally located a short walk from downtown Big Timber, this cottage is a comfortable base for your Montana stay. The space is bright, airy, and designed to feel peaceful and relaxing. The kitchen includes everything you need to prepare meals, and there is a dedicated desk for those who need to work remotely. Its convenient location makes it a great choice for visitors coming to Big Timber to spend time with family or attend local events, while still enjoying your own space.

Absarokee - Cozy Cottage

This cottage is located in the heart of world-class fly-fishing, hiking, river rafting, and horse-back riding. At the base of the glorious Beartooth Mountains, we are 30 minutes from Red Lodge Ski Mountain, Tippet Rise Art Center and within two hours of Yellowstone National Park. Our property is within 100 feet of Main Street which features a local grocery store, laundromat, & restaurants plus the incredible nightlife is only a few feet away.

Home Sweet Home on Broadway

Less than a 5 minute walk to all that Red Lodge has to offer downtown. Whether you are here to enjoy the outdoors, drive the Beartooth Pass to Yellowstone or heading to Red Lodge Mountain to ski, Home Sweet Home on Broadway is your home away from home. Relax on the back deck, enjoy the hot tub and our fenced in yard. We are happy to welcome 2 dogs, but please remember to include them in your booking. We do ask a pet fee of $25.

Haven at Rock Creek, Luxury Meets the River's Edge

One of two homes on 16 private acres with direct access to Rock Creek—step outside and fish right on the property. This modern retreat features a chef’s kitchen with a Wolf gas range, a floor-to-ceiling double-sided fireplace, and plenty of privacy between homes. Perfect for relaxing getaways or for additional fees host a special occasion. Message us for details! See more photos and updates on social media @havenatrockcreek

Bramble House Inn

The all but faded charm of a historic 1908 home has been resurrected into the beautiful Bramble House Inn featuring 5 bedrooms and 4 baths in a total of 4600 sq. ft. Make our beautiful home or just a room yours, your family's, or your group's for a night, week or even longer any time of the year. We look forward to meeting and hosting you here at the Bramble House Inn!