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.

ValueLocationLaundry

4.99 out of 5 average rating, 392 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

ValueLocationAccess

4.98 out of 5 average rating, 314 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!

ValueFamilyCondition

4.96 out of 5 average rating, 113 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!

FamilyLocationAmenities

4.97 out of 5 average rating, 29 reviews
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

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.

FamilyLocationQuiet

4.99 out of 5 average rating, 129 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.

ValueLocationLayout

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 .

ValueFamilyHiking

4.9 out of 5 average rating, 830 reviews
Top Guest favourite
A spacious log cabin is nestled among lush greenery, featuring a covered front porch with wooden railings and rocking chairs. Large windows provide natural light, while smooth stones and vibrant grass enhance the outdoor landscape. Surrounding trees add to the serene, wooded setting.
Home in Nye

River Island House - Riverfront Luxury & Seclusion

Enjoy private luxury in this 2-story cabin at the water's edge on a wooded island. Located on the scenic West Fork of the Stillwater River, you'll find serenity in this beautiful area. Blue-Ribbon trout fishing. Secluded, but a short drive to hiking trails, the Nye Trading Post (convenience store/gas/post office), and Carter's Camp bar/restaurant. Please note: No smoking. The Pet Fee is $50 per pet. Please contact us in advance if more than one pet. Caretaker lives nearby.

FamilyValueAccuracy

4.99 out of 5 average rating, 81 reviews
Top Guest favourite
A rustic cabin is framed by tall trees, with a porch showcasing large windows that invite natural light. A stone wall borders the yard, with patches of grass and boulders scattered throughout. The property features a serene outdoor setting with clear blue skies above.
Cabin in Nye

Rustic Riverfront Family Cabin on Stillwater River

Private river access to the scenic Stillwater River with world-class fly fishing just out your door. Cabin and porch overlooking the rushing water in a unique rural setting surrounded by stunning cliffs and abundant wildlife. Large lot with plenty of outdoor space for games and activities. Get to know the area where Montana locals vacation away from the throngs of tourists; close enough to visit a hotspot destination on a day trip, but far enough away to have your quiet space.

FamilyValueOutdoor spaces

4.97 out of 5 average rating, 66 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.

LocationValueNearby

4.96 out of 5 average rating, 71 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!

LocationFamilyCheck-in

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!

FamilyValueBathroom

4.98 out of 5 average rating, 320 reviews

Popular amenities for Stillwater County holiday rentals