Vacation rentals in Winston

Spacious artist's studio loft apartment with view

Relax at this charming, remodeled studio, stunning views of The Sleeping Giant. A short drive or bike ride from downtown Helena, Archie Bray Foundation, and nearby parks/trails. 10-Mile Creek & Spring Meadow Lake under a mile away, w/Mt. Helena trails just outside. Studio features a butcher block counter kitchen, gourmet stove, cookware & table settings. Wifi, Organic Coffee, Espresso maker, parking included. No smoking on property; off site only, No early check-in, Keep pets off furniture.

"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!

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.

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.

Black Mountain Chalet

Nestled in the Aspens, a stones throw away from Colorado Creek, is where you will find the Chalet. Thoughtful touches and ample amenities, ensure guests will experience an enchanted getaway. The surrounding meadows and forested areas offer hiking and a range of flora/fauna viewing opportunities. We invite you to experience the tranquility of this private wonderland setting located close to Helena, Broadwater Hot Springs and The Wassweiler Dinner House.

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!

Secluded Cabin 2 surrounded by National Forest

2 night minimum. Pets allowed with approval. All dogs are required to be on a leash and under supervision around the lodge and cabins. 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... Arrival before dark is recommended. NO HUNTING ON OR FROM THE RANCH

Hauser Haus- Walk Downtown or to Carroll College

Tuck into a peaceful home-away in this spacious and serene space just a few minutes walk from downtown Helena or the hiking and biking trails of Mount Helena. This daylight walkout basement faces a large yard with mature maple trees and substantial off-street parking. The kitchen has been stocked with necessities for easy cooking during your stay. Bring your favorite coffee, we have a grinder.

Oro - Forest hideout, minutes to town

Nestled in the National Forest, just minutes to town. Watch wildlife in the yard, listening to the crackle of the wood burning stove. Relax in the hot tub gazing at the stars among the trees. Spread out in the spacious kitchen or enjoy the aroma of the smoker grill by the fire pit. Seasonal Note: Hot tub is available March through October. Hot tub is not available November through April.