Vacation rentals in Winston

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!

"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.

Cozy, charming basement on the west side

Welcome to our bright, happy basement apartment where you'll find the perfect blend of cozy 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

Stylish studio close to the Walking Mall

You are sure to love this studio which is just a stones throw from Helena’s famous walking mall. With restaurants, bars and breweries all within a short walking distance, you’ll have everything you need close by. You’ll be staying in a piece of history. The building is the oldest mansion in Helena, built in 1868 and has been divided into multiple different units. This one has its own entrance at the rear of the property. Please note that it is on the second story so there are stairs!

Giant View Home

Enjoy a cozy stay with stunning views of The Sleeping Giant in this spacious home for up to 6 guests. Just minutes from downtown, the Archie Bray Foundation, parks, and hiking trails, it's the perfect base in Helena. Ten Mile Creek and Spring Meadow Lake are under a mile away, with Mt. Helena trails right outside. Wifi, Organic Coffee/Espresso, and parking are included. No smoking anywhere on the property; smokers must step off-site. No early check-in. Keep pets off furniture.

Creek front chalet with hot tub and sauna

Welcome to @thebighornchalet— a creek front, modern A-frame. At a full 750 square feet, you'll enjoy the regular luxuries of a full-size home without sacrificing comfort! Enjoy the hot tub, steam sauna, fire pit and picnic area that are next to Trout Creek, which runs through the entire property. Located just a few miles from both Canyon Ferry Lake and Hauser Lake you can enjoy the great outdoors. Or head into Helena, MT just 20 miles to enjoy all the town has to offer.

Romantic Montana A-Frame | Hot Tub & 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.

Birds & the Bees

The Birds&Bees (B&B) is tucked away in the south hills and yet walking distance to downtown. You will be close to Grateful Bread Bakery, the library, Blackfoot River Brewing Co. and the infamous Windbag Saloon. For fine dining On Broadway restaurant is there, as well. For eating in, you can take a short drive down the hill to the Real Food Market & Deli for fresh, organic groceries. Welcome to Helena and explore what it has to offer.

Executive Cottage-Walk to Trails/Downtown

Stay in a centrally located house at the base of Mt. Ascension! House is well appointed with new mid-century modern furniture. You'll be within an easy walking distance to downtown and the Capital complex. There is an amazing trail system for hiking and mountain biking just two blocks south. We offer key-less entry to make check-in a breeze. A 400 MB internet service is provided for traveling professionals.

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.

Secluded Cabins surrounded by National Forest 1

2 NIGHT MINIMUM REQUIRED / pets allowed with approval. All dogs ae required to be on a leash and under supervision when on the property. The property is a 65-acre guest ranch surrounded by the Helena National Forest on all sides. There is a 3 mile forest road that climbs over 1,000 feet to the ranch property. Guests enjoy solitude, views, wildlife...

Miners Cabin

Recently renovated historic miners cabin detached from the Free Enterprise Radon Health Mine. Guests receive a spectacular view of the Boulder Valley. In addition to this being a unique experience it also serves as a great home base for exploring area ghost towns, fishing local rivers and is surrounded by public land for hiking or hunting.