Holiday rentals in Winston

"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.

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.

Romantic 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 Clarke Street "Mini-Vic"

Built in 1890, this "mini" Victorian is a block from Mt. Helena's superb biking/hiking trails and 5 blocks from breweries, restaurants and the historic Last Chance Gulch. Recently updated, the Mini Vic still maintains its 19th century charm. Spacious kitchen and bath, formal dining and an inviting living room with gas fireplace. Cozy outdoor space with gas BBQ and firepit. Great location and a great little home while you enjoy Helena!

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

Centrally-located studio apartment with a view!

This comfortable, well appointed studio apartment overlooks downtown Helena and the surrounding valley. Two blocks from the Montana State Capitol building, and a short 20-minute walk from the historic Last Chance Gulch shopping/dining district, this beautiful place comes equipped with a king-sized bed, a full-sized futon, a well-stocked kitchen, and a private bathroom. Did we mention the views?

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.

Stylish home close to trails & downtown

This quaint, chic, newly updated home offers everything you'd want in an Airbnb. It's beautifully redesigned and significantly solar-powered making it eco-friendly and luxurious at the same time. This little retreat is a stand alone 1 bedroom home on a quiet, scenic street.

West Side Upstairs Studio

West Side upstairs studio with a beautiful view of Mt. Helena and the lights of the north valley at night. Quiet, tree filled neighborhood. Walk to downtown, Carroll College, Civic Center, breweries and restaurants. Off street parking at the stairs leading up to the studio.