Holiday houses in Winston

Cozy Mid-Century Guest Suite

A recently remodeled mid-century guest suite in the heart of Helena. The suite features zero step entry, a queen size bed, closet space, high quality bedding, microwave, mini fridge, coffee pot, AC, and natural light throughout. A comfy, wide couch with bedding can be used in the living room for an extra bed. Brand new shower and replaced flooring in every room. Easy access to I-15, a quick drive to downtown Helena which is full of microbreweries, eateries and shopping, and close to the Capitol.

"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

Modern Victorian - walk to downtown and trails!

Our beautifully remodeled Modern Victorian home is perfectly located for you to enjoy all that Helena has to offer! Walk downtown, to multiple trailheads, or to the State Capital -- all just about ten minutes from your doorstep! This lovely home is on the National Register of Historic Places offering you a little experience of Helena's deep history. Up to six guests can enjoy the stylish comfort this home provides with a queen bed, a twin daybed with twin trundle, and a queen sleeper sofa.

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.

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.

Silver Creek Accessible Studio

Enjoy a bright and welcoming accessible studio suite just 10 minutes from Helena’s city limits. This thoughtfully designed space features a full kitchen and an extra spacious, wheelchair-friendly bathroom with a roll-in shower—large enough to comfortably accommodate a caregiver and a shower chair. Whether you're visiting for business or relaxation, this cozy retreat offers both comfort and convenience in a peaceful setting.

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.