Holiday rentals in Stillwater County

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Top-rated holiday rentals in Stillwater County

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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
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, 357 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
Cabin in Roberts
4.99 out of 5 average rating, 285 reviews

1865 Historic Cabin w/hot tub. Close to 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 single-story house is set against a clear blue sky, surrounded by lush green grass. Several trees with budding foliage are visible in the yard, creating a serene landscape. A driveway leads to the house, with outbuildings located nearby.
Cottage in Joliet
4.96 out of 5 average rating, 235 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.

Guest favourite
A cozy living area features comfortable leather sofas arranged around a wooden coffee table. A flat-screen TV is positioned on a metal stand. Natural light fills the space through a large window, showcasing views of the surrounding area. The open layout connects to the kitchen and dining area.
Townhouse in Red Lodge
4.85 out of 5 average rating, 108 reviews

Black Bear Den- Mountain Views - Close to Downtown

This condo is perfectly situated just a minute from downtown Red Lodge while getting the amazing mountain views of the Beartooths, Mt. Maurice, and Red Lodge Mountain. Inside enjoy all the western details throughout the home from Montana Cowboy to Mountain Wildlife, modern amenities and all of the necessities to make you feel right at home. There are walking trails that take you along the scenic West Bench and the Rodeo Ground which hosts popular events such as the Home of Champions Rodeo.

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, 762 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 .

Superhost
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
4.92 out of 5 average rating, 252 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 favourite
A cozy sleeping area features a quilt adorned with wildlife motifs, complemented by decorative pillows. Warm wood paneling creates an inviting space, accompanied by soft lighting from mounted sconces. A framed nature-themed artwork enhances the rustic charm of the room.
Guest house in Park City
4.97 out of 5 average rating, 381 reviews

NEW Charming Little Cottage in Park City, Mt

Brand New! Super cute little cottage tucked away in the back yard with a contemporary farmhouse/rustic charm to it. Located right off I-90. Less than 10 minutes from Laurel ( which has Walmart, fast food, grocery store, restaurants). 25 minutes from Billings and 20 minutes to Columbus. Private entrance. Perfect for the traveling worker, couple or solo adventure. Wifi is available with a smart TV so you can watch your shows on your favorite apps (Netflix, HuLu, ect.)

Top guest favourite
A cozy living room features a sectional sofa and a patterned accent chair, complemented by a round wall clock. Two windows are adorned with patterned curtains, while a television is positioned on a stand. Light from lamps enhances the neutral color scheme.
Cottage in Red Lodge
4.93 out of 5 average rating, 136 reviews

Beartooth Bungalow

This one bedroom cottage is the ideal jumping off point into the Beartooth Mountains. It is an ideal set up for couples and singles but will accommodate small families. Located just a block off of Broadway in Red Lodge, MT you can walk downtown & have dinner and drinks in minutes, or be skiing, golfing or hiking, or traveling the Beartooth Highway in 10 minutes. This little cottage has everything you need to make this your home away from home.

Top guest favourite
The front of a charming white house is showcased, featuring a wooden door and welcoming rocking chairs on the porch. A flower box adorned with white flowers hangs beside the window, and a flag can be seen in the background against a blue sky filled with clouds.
Home in Red Lodge
4.99 out of 5 average rating, 172 reviews

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.

Top guest favourite
The exterior of a unique reclaimed silo features a cylindrical design with corrugated metal siding. Multiple large windows allow natural light to enter, and a glass door provides access. Surrounding greenery and rocks complement the structure's rustic charm in a serene landscape.
Farm stay in Greycliff
4.97 out of 5 average rating, 142 reviews

The Fox Den Silo

Enjoy crisp mornings in this unique reclaimed silo. These silos are featured in the TV show Restoration Road. Originally saved from destruction in the Dakotas, these have been turned into unique homes situated at the base of the Greycliff for which the town was named. Enjoy watching the buffalo with their newborn calves roam the fields while relaxing in the hot tub or making memories in the beautiful Montana countryside!

Top guest favourite
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, 303 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!

Popular amenities for Stillwater County holiday rentals