Vacation rentals in Stillwater County

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Top-rated vacation rentals in Stillwater County

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A rustic log cabin is nestled among vibrant autumn foliage, with golden leaves contrasting against the wooden structure. The cabin features a porch and is surrounded by tall trees, while a mountain peak rises in the background under a clear blue sky.
Cabin in Reed Point
5 out of 5 average rating, 115 reviews

Packsaddle Butte Guest Cabin Retreat

The perfect getaway to a charming and cozy log cabin in stunning landscape bordering Nat'l Forest. Hiking and 4-wheeler trails abound. Next to a running creek and pond. Electricity, wood stove, outside toilet, heated outdoor shower, 2 twin beds, TV, BluRay player, microwave, mini fridge, firepit with grill/griddle and picnic tables. Idyllic porch for sitting under trees, birdwatching, reading, or relaxing. Snowshoeing, sledding, & cross country skiing in winter. Ideal for 2 adults w/cot for 3.

Top guest favorite
The cottage's exterior is framed by natural logs and stones, highlighting large glass windows that extend along the structure. Located in a grassy area, the building creates a seamless connection to the surrounding landscape under a clear blue sky.
Cottage in Roberts
5 out of 5 average rating, 42 reviews

Glass Cottage Overlooking Beartooth Mountain Range

This spectacular, exquisite cottage is the perfect getaway spot for those looking for secluded privacy with a million dollar view! Perched atop a hill overlooking the Beartooth Mountain Range, the Glass Cottage lives up to its name! Breathtaking views of the picturesque mountains can be seen from every room in this luxurious log cottage through the large, glass windows. On beautiful days, you can open up all the sliding glass doors to have the full Montana experience with the fresh mountain air!

Top guest favorite
A rustic log cabin is set amidst lush greenery, featuring a welcoming front porch supported by sturdy wooden beams. Nearby, a stone patio is complemented by picnic tables, inviting outdoor gatherings. The surrounding landscape includes trees and well-maintained grass, creating a serene setting.
Cabin in Roberts
4.99 out of 5 average rating, 145 reviews

Private Luxury Log Cabin near Red Lodge, MT

Private luxury one (queen) bedroom log cabin with a queen sofa bed, full bathroom (shower), radiant floor heat, ceiling fans, beautiful rustic furnishings, and a kitchenette. This beautiful cabin sits on 10 pristine acres that border Rock Creek (prime fly fishing) and Red Lodge ski mountain is only minutes away. Enjoy camping and hiking in the summer and drive over the scenic Beartooth Pass to get to Yellowstone Nat'l Park. This truly is a one-of-a-kind location to spend with friends & family!!

Top guest favorite
Cabin in Roberts
4.98 out of 5 average rating, 306 reviews

Renovated Historic Cabin w/ Hot Tub Near Red Lodge

*Pls see other listing for winter bookings ! Only sleeps 2 in winter. Nestled in the town of Roberts, a short drive from Red Lodge, Kodow Kabin is a perfect retreat for a getaway. While the exterior is log, the inside is renovated & beautifully decorated. The cabin is 1 bed/1 bath for 2 guests w/ detached bunkhouse (may-Oct) for 2 more guests! The kitchen has a farmhouse sink, and cabinetry made from the siding that covered the logs. Use the private deck to BBQ or hot tub soak under the stars

Top guest favorite
A well-lit living room is furnished with a dark sectional sofa and patterned armchairs. A side table holds a lamp, while large windows provide a view of the outside. An open doorway leads to the dining area, enhancing the spacious feel of the interior.
Home in Big Timber
4.98 out of 5 average rating, 125 reviews

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!

Guest favorite
A log cabin interior features a spacious bed with a patterned blanket, complemented by a cozy chair positioned near a large window. Exposed wooden beams and a rustic ceiling create an inviting atmosphere. Soft light is provided by a lamp beside the bed.
Cabin in Greycliff
4.92 out of 5 average rating, 220 reviews

The Buffalo Jump

Need a quiet place to celebrate your anniversary, have a night away from the hustle of work and life, or just passing through? You have found the right place. This restored historic log cabin is the perfect getaway. Conveniently located just off of I-90 in Greycliff. Enjoy a beautiful sunset in the hot tub or making memories around the fire pit! To top off your stay and make it the best experience, drive, 1/4 mile to the Greycliff Mill and enjoy a cup of coffee and a fresh cinnamon roll.

Top guest favorite
The rustic cabin is illuminated under a clear night sky, showcasing its warm wooden exterior. The surrounding tree branches frame the scene, while the full moon casts a gentle light over the grassy area and wooden deck, creating a serene outdoor atmosphere.
Cabin in Fishtail
5 out of 5 average rating, 22 reviews

Stargazers Sanctuary

Nestled in the foothills of the Beartooth mountains, the Sindelar cabin is a serene stay at Bench Ranch. West Rosebud creek is within walking distance, as well as several other lovely areas to explore in the foothills. Nearby you have access to Mystic Lake, Emerald Lake, Tippet Rise Art Center, and many more outdoor activities. You will be amazed at the night sky which is perfect for stargazing. And during the right time of year, you may witness the elk herds moving through the valley.

Top guest favorite
A spacious kitchen is equipped with modern appliances, including a refrigerator and microwave. Natural light filters through an arched window above the sink, illuminating the counters. A wooden dining table with seating is positioned near the window, creating an inviting cooking area.
Loft in Park City
4.92 out of 5 average rating, 242 reviews

Rustic loft Apartment with a view in Park City

Super cute apartment above the garage. All new. Very rustic decor. Very cozy for a solo adventure or a couple. Nice big kitchen with everything you need to cook. 43 inch TV with access to Netflix. Free Wifi is available to our guests. Queen size bed with memory foam mattress. Window over kitchen sink has a view of our back yard and kio pond. Complete privacy. Also has a washer and dryer for guests to use in the unit. This place is a perfect home away from home for traveling workers.

Guest favorite
A panoramic view of mountains is visible in the distance, framed by a backdrop of tall evergreen trees. The landscape showcases a mix of rolling hills and open spaces, under a clear blue sky with soft clouds.
Cabin in Columbus
4.93 out of 5 average rating, 258 reviews

Wells Rustic Cabin

Our cabin has a beautiful view of the crazy mountains with deer and turkeys frequenting the property. You are close enough for day trips to Red Lodge, MT, Yellowstone Park and many more. Half way between Billings and Bozeman. The Stillwater and Yellowstone Rivers are close for fishing and rafting. Hiking trails are close also. It does have 2 miles of rough road. Real 4WD is recommended especially for mud (ruts/slippery) and snow drifts/ ice(might need chains)on hill .

Guest favorite
Home in Absarokee
4.88 out of 5 average rating, 201 reviews

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.

Top guest favorite
A charming cabin is positioned on a gentle hillside, featuring a green roof and a wide porch. The surrounding landscape is composed of gently rolling hills covered in lush grass, creating a serene, natural setting under a clear blue sky.
Ranch in Absarokee
4.99 out of 5 average rating, 310 reviews

Indian Rock Ranch Cozy cabin w/ Mountain View

Located in the Stillwater Valley and Beartooth foothills, we are close to many Montana adventures, including wildlife viewing, fishing, hunting, hiking, Tippet Rise, whitewater rafting, horseback riding and downhill skiing. We are 30 minutes from Red Lodge. You’ll love our cabin for its clean, comfortable, relaxing and private atmosphere where the views are unbelievable. Our comfortable cabin is great for everyone!

Guest favorite
A rustic cabin with a wooden porch is set against a backdrop of rolling hills and pine trees. The structure features a green roof and a large front window, with a gravel path leading to a fire pit area.
Cabin in Fishtail
4.96 out of 5 average rating, 47 reviews

Deer Cabin - Mountain Views - Pet Friendly

Enjoy the breathtaking view of the Beartooth Mountain Range from the comfort of your cozy cabin, while being serenaded by the soothing sounds of the rushing West Rosebud Creek. This picturesque location is perfect for nature lovers seeking a peaceful getaway. This secluded retreat is sure to recharge your senses and leave you feeling refreshed. Book your stay today to experience this tranquil haven for yourself.

Popular amenities for Stillwater County vacation rentals