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 favorite

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, 112 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 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, 42 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

Cabin in Roberts

4.99 out of 5 average rating, 303 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 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, 249 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

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, 775 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 favorite

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 .

Top guest favorite

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

4.96 out of 5 average rating, 47 reviews

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.

Top guest favorite

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, 306 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!

Top guest favorite

A cozy bedroom is furnished with a queen bed featuring a rich burgundy coverlet, complemented by decorative pillows. Two lamps are situated on wooden nightstands beside the bed. Natural light enters through two windows, framed with red curtains, enhancing the serene ambiance of the space.

Apartment in Big Timber

5 out of 5 average rating, 80 reviews

Sweetgrass Cottage

The Sweetgrass Cottage is quaint and well-equipped suite located within walking distance of downtown Big Timber. The cottage includes free off-street parking right in front of the private entrance, a gas grill, fast Wi-Fi, A/C, and a washer/dryer (available by request), as well as many other items to help make your stay more enjoyable. Very peaceful and comfortable whether you are staying for a night or several months.

Guest favorite

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

4.96 out of 5 average rating, 47 reviews

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.

Guest favorite

A cozy living space is showcased, featuring a black recliner positioned near a dark wooden table. A plush area rug lies on the floor, and a large television is mounted on the wood-paneled wall. Natural light filters in through a window with dark curtains.

Apartment in Reed Point

4.93 out of 5 average rating, 28 reviews

Triple R Retreat

Experience the charm of Big Sky Country from the comfort of your own private retreat in Reed Point, Montana, where quiet evenings, star-filled skies, and small-town hospitality come together to create the perfect getaway. Whether you’re seeking adventure, rest, or a little bit of both, our cozy apartment is your home base for exploring all the beauty and peace Montana has to offer.

Guest favorite

A tranquil garden path made of stone leads to the cabin entrance, surrounded by lush green plants and colorful flower beds. A wooden fence encloses the area, providing privacy and a natural setting filled with greenery and decorative rocks.

Guest suite in Park City

4.87 out of 5 average rating, 795 reviews

Cozy little Cabin in Park city

Cutest little cozy and comfortable cabin in town. It has it's own deck With a beautiful view of flower gardens and a koi pond. The flooring and decoration are very country. This is right off the interstate. Quiet little town. 7 minutes from Laurel, 20 minutes from Billings. TV with access to Netflix. This doesn't have a kitchen but there is a microwave and mini fridge.