Vacation rentals in Stillwater County

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Top-rated vacation rentals in Stillwater County

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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, 28 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, 136 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

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, 334 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 favorite

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, 196 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 favorite

A serene riverfront view showcases a cabin with large windows overlooking the Stillwater River. The exterior features red wood siding and a covered porch, while the lush green grass leads down to the water's edge, framed by tall trees and mountains in the background.

Cabin in Columbus

5 out of 5 average rating, 9 reviews

“Where The Wild Things Are” Fly Fishing Cabin NEW

Resting serenely on the Stillwater River, a Blue Ribbon trout stream in the foothills of the Beartooth Mountains, this fly fisherman’s paradise offers 2 house fly rods, 2 men’s/1 child’s waders & boots, and a fly tying station with all the materials an angler could need. Guests enjoy a bar, fire pit, darts, cards, chess, a house guitar & river views from every room! Ideal for 2 families w/ 2 queen beds (1 open to loft) & 6 loft twins! Only 40 min to Red Lodge Ski Resort w/ no lift lines!

Top guest favorite

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, 108 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.

Guest favorite

A rustic log cabin stands amidst lush greenery, featuring a spacious porch with wooden railings. Large windows allow natural light to fill the interior, while the sturdy stairs offer access to the inviting entrance. The surrounding landscape provides a tranquil setting.

Farm stay in Big Timber

4.88 out of 5 average rating, 114 reviews

Metcalf Ranch Cabin

We welcome you to the Metcalf Ranch, which was featured on the Montana segment of the Anthony Bourdain show, "No Reservations." Beautiful Lower Deer Creek is just a one minute walk away, and guests are invited to enjoy the creek and explore the 1000 acre ranch. We are just 10 minutes from Big Timber, which has restaurants, shopping, golf and a movie theater. You’ll love the cabin because of the solitude, the beauty, the location, the ambiance, and the ranch atmosphere. We allow pets.

Guest favorite

A single-story house is situated on a grassy lot, featuring a stone-accented side and a covered porch with white chairs. Sunlight gently filters through the trees, creating a serene atmosphere in the surrounding yard.

Home in Joliet

4.85 out of 5 average rating, 118 reviews

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.

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

4.93 out of 5 average rating, 249 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 .

Top guest favorite

A hot tub is situated outdoors, offering panoramic views of the surrounding landscape. The clear blue sky and bright sun reflect off the water, enhancing the sense of tranquility. Lush greenery and distant hills can be seen in the background, creating a serene atmosphere.

Home in Red Lodge

4.98 out of 5 average rating, 116 reviews

*Amazing Views *Hot tub *Fire Pit* Modern

Come relax at this beautiful, open-concept home overlooking Red Lodge with incredible views! This 3 bedroom home has the perfect mix of rustic and modern design and although it is just a few minutes to town, it sits on a private 3 acre lot and feels incredibly private. Enjoy the sunset from the hot tub, a BBQ on the covered deck, or marvel at our local wildlife while swinging on the porch swing. We are also just minutes to the ski hill and many hiking trails as well.

Guest favorite

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.

Guesthouse in Park City

4.97 out of 5 average rating, 348 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.)

Superhost

The living room features a red sofa, a patterned gray armchair, and a coffee table with a selection of books. A small dining area with high chairs is visible in the background. A map of the United States is displayed on the wall, complemented by modern decor.

Home in Absarokee

4.88 out of 5 average rating, 184 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.