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 favourite
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, 111 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 favourite
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, 144 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 favourite
The cabin's exterior features a wooden porch supported by log pillars. Two comfortable chairs are placed invitingly on the porch, with a landscaped path leading up to the entrance. Snow remains visible in some areas, contrasting with the rustic wooden siding.
Cabin in Roberts
4.99 out of 5 average rating, 299 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 favourite
A welcoming entry showcases a view of the grassy landscape beyond. Morning sunlight streams through the open door, illuminating the wooden interior. A picnic table is visible in the distance, framed by the serene backdrop of mountains and the river.
Cabin in Greycliff
4.99 out of 5 average rating, 368 reviews

The Cabin at the Hagerman Ranch

The Cabin is located on the west end of our family owned and operated cattle ranch. It has a full kitchen with everything needed to cook meals, a full bathroom, master bedroom with a queen size bed, small open loft with a pillow top double bed and 2 XL twin mattresses. The Yellowstone River is less then 100 ft from the front porch! Enjoy morning coffee watching the sun rise on the Crazy mountains, and in the evening sit on the front porch and relax & enjoy the beautiful sunset behind the mtns.

Top guest favourite
Cottage in Joliet
4.96 out of 5 average rating, 245 reviews

Peaceful Country Cottage - Gateway to Yellowstone

Farmlands surround you in this peaceful valley. Your house overlooks farm fields down to the Clarks Fork of the Yellowstone River. 2 min South of the Rockvale Junction (Highway intersect of the 212 and the 310). 1 Hour North of Cody, WY, 35 min from Red Lodge, MT. Take a scenic drive over Beartooth Pass into Yellowstone Park. Your house is a 2 bedroom, 1 bathroom. 2 min from the Edgar Bar & Steakhouse. 8 min away in Joliet is a local grocery store, Blackbrew Coffee, and Jane Dough's Pizza.

Top guest favourite
Home in Big Timber
4.98 out of 5 average rating, 122 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 favourite
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, 218 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 favourite
A rustic barn is positioned on a grassy expanse, under a dynamic sky filled with clouds of varying shades of gray and white. The barn features wooden siding and a porch that extends along the front, providing a view of the distant horizon.
Barn in Big Timber
4.99 out of 5 average rating, 116 reviews

The Bunkhouse at Sojourner Ranch

The Bunkhouse at Sojourner Ranch is a unique rustic experience of Romancing the west in the simplicity that was once apart of cowboy life. With endless miles of rolling hills and grasslands, wildlife is plentiful, and the sunrises and sunsets paint the sky with deep rich colors. The sweet melody of the Western Meadowlark and the Sagebrush Sparrow serenade you all through the day and the clear nights reveal billions of stars and the Milky Way. Checkout @thebunkhouseatsojournerranch on IG.

Top guest favourite
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, 20 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 favourite
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, 236 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.

Top guest favourite
The exterior of a cozy cottage features a gray-blue facade and a yellow front door. A small porch is furnished with a bench and chairs, surrounded by a well-maintained lawn. A pathway leads to the entrance, with trees and a fence visible in the background.
Home in Red Lodge
4.91 out of 5 average rating, 771 reviews

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 .

Guest favourite
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, 255 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 .

Popular amenities for Stillwater County vacation rentals