Holiday 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

Secluded A-Frame/Hot Tub/K Bed/Fireplace/Mtn View

Experience an unforgettable getaway at The Little Black A-Frame. This stunning cabin nestled on 20 acres and surrounded by sweeping mountain views, was thoughtfully curated with couples and friends in mind. Perfect for a romantic getaway or girls trip, guests will find a private and peaceful setting to relax and connect. 22 min to Helena Airport 1.5 hr to Bozeman Airport Located between Yellowstone & Glacier National Park Follow us on IG @Littleblackaframemontana to view more pics & video

Benton House - guest suite, no cleaning fee

Located in the heart of the original town site for Helena, the Benton House provides great access to downtown, the mountain trails, and all that is wonderful about Helena. We are owner occupied, you will be staying in a recently redecorated private suite on the 2nd floor of our Victorian home. The Benton House is 2 blocks from the walking mall, less than a mile to the trailheads on Mt. Helena and Mt. Ascension. We are also very conveniently located to the Capital and to Carroll College.

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.

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.

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.

Newly Renovated, Charming, Downtown Cottage

This newly renovated, charming cottage is perfect for a quiet getaway or your week of outdoor adventure. Whether you are going zip-lining in Yellowstone National Park, enjoying the hot springs in Bozeman, or fly fishing in Livingston, this quaint vacation house is the perfect home base during your trip.