Vacation rentals in Winston

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

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!

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!

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.

Elkhorn Mountain Ranch

We are located in beautiful Clancy, MT, 10 miles south of Helena, MT. We are tucked away in the forest, very private and beautiful location with outdoor exploring right outside the front door! We are close to Interstate 15 and the Clancy exit and are minutes away from restaurants in Clancy and 10 minutes away from Helena restaurants and shopping. Our guesthouse is very clean, modern and inviting and a great place to stay during your Montana adventure!

Canyon Ferry Cottage

Relax with the whole family at this peaceful place to stay with views of Canyon Ferry Lake and the Elkhorn and Big Belt Mountains. The guesthouse features 2 bedrooms and 1 bathroom. Room 1 features a queen size bed. Room 2 has a bunk bed with full size bed on the bottom and twin on top. The bathroom features a walk-in tile shower. This is the perfect location to enjoy the Helena-Townsend area including Canyon Ferry Lake!

Oro Nest - Hideout min from town

Kick back and relax in this calm, stylish space. This is a Studio apartment above a detached garage adjacent to the main house. This is a shared property with the main house that is also an Airbnb. (The main house is not part of this listing). You can book the main house separately. The Nest offers 3 beds. 1-Queen, 1- Twin couch sofa, and 1-twin blow up mattress all within the studio space.

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.