Vacation rentals in Winston

Cheerful 1 Bedroom Luxurious Suite w/Hot Tub!

The Lillie Pad Awaits Your Arrival... Come home to your Ultimate, Mountaintop Luxury Glamping-Suite w/ brand new hot tub - Majestic Mile High Ranch beauty at its best! Total seclusion with world class views of the rocky mountain front and continental divide, only minutes from Montana's Capital. Meticulously handcrafted in the center of the CanyonRidge Ranch, which borders the immense Helena National Forest & lush mountain meadows... Makes the Lillie Pad a truly one-of-a-kind experience and stay!

Helena Forest Hideout w/ Hot Tub Near Downtown

Stay inside Helena National Forest, yet only 7 minutes from downtown Helena on a well-maintained paved road. The home sleeps 9 and features a large yard frequented by wild-life. Enjoy the huge kitchen, covered porch on the rocking chairs, a grill, Traeger smoker and a seasonal hot tub available April through October. In cooler weather, settle in by the wood-burning stove, with central heat for added comfort. Need more space? The separately listed guest house sleeps 3: airbnb.com/h/oronestmt

"Caretakers Apartment"

The Caretakers Apartment is located in the Lodge of Townsend. The Lodge is conveniently located 1 block of Main Street, close (1 block) to Heritage Park and shopping. Canyon Ferry Brewing is on the same block. The Lodge of Townsend hosts a daycare/preschool, a speech therapist, as well as rooms for rent . The apartment has a fully equipped kitchen with service for 4. The full size sleeper sofa in the living room provides an additional place to sleep. The den can be used for an offfice.

Pretty Cool Crib-No cleaning fee

Enjoy your stay in this stylish "new build". The original home was built in 1900 but the home has been updated down to the framing. The home is centrally located with easy access to shopping, restaurants, and the interstate. Extra amenities include a king-size adjustable bed with massage in the master and a Bose Soundbar for a superior listening experience while watching TV or listening to music. We're positive that you will find this home comfortable and your stay enjoyable. No cleaning fee!

Family Adventure House-Climbing Wall+Hiking Trails

Bring the whole family to this spacious townhouse in South Helena's Nob Hill neighborhood! It's the perfect place to stay while you go on your next adventure- mountain biking & hiking trails are within walking distance. Take in the mountain view on the patio, play ping-pong or watch the kids boulder the climbing wall. We also have a home gym & there's a frisbee golf course that is 1/2 a block away! Located close to hospitals & has easy-access to I-15. Only 10 min. from historical downtown.

The Iron Mask Cabin

Beautiful Canyon Ferry Lake views in this adorable pet-friendly cabin. Two bedrooms easily sleep 5 comfortably. The first bedroom has a dreamy queen bed. The second bedroom has a twin over full bunk-bed for adults or children! Full bathroom with tub and shower. Also, a half bath with laundry facilities. Fully stocked brand new kitchen! This lake-view oasis also has a gas grill on the covered porch with patio furniture so you can enjoy the fully-fenced back yard complete with doggie door!

Cozy, charming basement on the west side

Welcome to our cozy, happy basement apartment where you'll find the perfect blend of comfort and underground allure! We are located on Helena’s west side. Centrally located to downtown, Spring Meadow lake, Broadwater hot springs, and hiking and biking trails. Our spacious basement apartment boasts all the essentials for an unforgettable stay! The kitchen and bath are equipped with all the amenities you need. The decor is comfortable with just a little twist of humor and good spirit.

Ranch House in the Elkhorn Mountains

The Ranch House is on a 900 acre cattle ranch in the Elkhorn Mountains about 25 minutes outside of Helena. We are close to the attractions of Montana's capital city, but nestled on top of the mountains, perfect for enjoying a true Montana outdoor experience. We have hiking and biking trails out the front door with abundant wildlife in the area. We are a perfect halfway point for travelers visiting both Glacier and Yellowstone National Parks looking to keep an authentic Montana feel.

Loft on Broadway

Located in the old Power Townsend building in the heart of Townsend, Montana, the Loft on Broadway is an updated space with old town charm. Built in 1910 and completely renovated in 2023, it boasts the original red brick walls inside the apartment and a central downtown location. With each booking we include a $25 gift card to Deep Creek Pizza, conveniently located just below the Loft! Two bedrooms, two bathrooms and an open kitchen and living area make this place a gem!

Secluded Montana A-Frame with Hot Tub and Views

Escape to your own Montana sanctuary at The Little Black A-Frame! This stunning retreat is nestled on 20 private acres with sweeping mountain views. Thoughtfully designed for romantic getaways and intimate friend trips, find yourself relaxing in the hot tub under starlit skies, enjoying cozy evenings by the fire, and crisp mornings on the patio watching the sunrise. Located between Yellowstone and Glacier National Parks, this is your gateway to Montana's wilderness.

The Hideaway at Creekside Meadows-Hobbit House

Nestled in the foothills of the Elkhorn Mountains you’ll find our charming earth home. Clean Scandinavian style decor allows the magnificent construction of this home to shine. A few unique features include 4 full sized built in sleeping nooks each with their own lights and electrical outlets, a secret door to a hidden private bedroom, and a shower you enter through a ‘tree trunk’ with almost 13ft ceilings!

little cabin on the prairie

A little piece of paradise nestled in the hills for relaxing with the family. Just far enough off the beaten path, for that peace and quiet, but still close enough to major surrounding towns. Is a short drive to trail heads for crow creek falls or lake, many trails and roads for exploring. Road to cabin is dirt road may not be suitable for very low profile cars.