Holiday houses in Stillwater County

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Top-rated holiday rentals in Stillwater County

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

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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

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.

FamilyLocationWalkability

4.99 out of 5 average rating, 393 reviews

Top Guest favourite

Cabin in Roberts

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

FamilyLocationComfort

4.98 out of 5 average rating, 315 reviews

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

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.

FamilyValueCheckout

4.97 out of 5 average rating, 270 reviews

Guest favourite

A wooden deck is presented with two adirondack chairs, offering an unobstructed view of the expansive green fields. A colorful sunset occurs in the background, with shades of orange and purple contrasting the gray clouds above. The serene landscape is softly illuminated by the evening light.

Farm stay in Reed Point

The Rockin’ K Bunkhouse; luxury in the country!

Welcome to the Rockin’ K! This building has been updated with modern conveniences set in beautiful natural surroundings. Not a made for tourist accommodation—this is the original bunkhouse on a 100 year-old farm. Enjoy a peaceful setting within two hours of Yellowstone park and the scenic Beartooth Pass. Breakfast fixings included, discount at the local Waterhole, abundant parking and easy freeway access! Kick back on the deck and enjoy sunset views over the river. Come get your Dutton on!

FamilyValueHiking

4.97 out of 5 average rating, 116 reviews

Guest favourite

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

"Where The Wild Things Are" Cabin Stillwater River

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!

LocationValueKitchen

4.97 out of 5 average rating, 29 reviews

Top Guest favourite

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

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.

FamilyValueRiver

4.87 out of 5 average rating, 134 reviews

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

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 .

ValueFamilyPets

4.9 out of 5 average rating, 832 reviews

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.

Guesthouse in Park City

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.)

LocationValueBackyard

4.96 out of 5 average rating, 422 reviews

Top Guest favourite

The cabin's exterior features natural wood siding and a welcoming front porch adorned with carved wooden accents. Flower baskets hang alongside the entrance, which is framed by large glass doors. The surrounding greenery offers a serene backdrop, highlighted by the cabin's rustic charm.

Cabin in Red Lodge

Bear Lodge

At Bear Lodge, your Montana mountain getaway begins the moment you arrive. Located in the beautiful Beartooth Mountain foothills, this cozy studio cabin offers the privacy of the woodlands but with the convenience of being located only 5 minutes from downtown Red Lodge. So whether you're here to ski, hike, fish, or take part in the many festivities in town, Bear Lodge puts you at the heart of Red Lodge's year-round outdoor paradise.

ValueFamilyBathroom

4.96 out of 5 average rating, 72 reviews

Top Guest favourite

A circular bedroom showcases a spacious bed adorned with white bedding. The wooden walls create a warm environment, while two bedside lamps offer soft lighting. A clock is mounted above the bed, and a textured area rug lies on the hardwood floor.

Farm stay in Greycliff

The Eagle’s Nest Silo

Enjoy crisp mornings in this unique reclaimed silo. These silos are featured in the TV show Restoration Road. Originally saved from destruction in North Dakota, these have been turned into unique homes situated at the base of the Greycliffs 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 on top of the Eagle’s Nest landing!

FamilyValueQuiet

4.96 out of 5 average rating, 165 reviews

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.

Farm in Absarokee

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!

ValueFamilyAmenities

4.98 out of 5 average rating, 320 reviews

Guest favourite

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

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.

FamilyLocationBarbecue

4.95 out of 5 average rating, 63 reviews