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

Cozy Mid-Century Guest Suite

A recently remodeled mid-century guest suite in the heart of Helena. The suite features 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 complex.

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.

Loft on Broadway

Located in the old Power Townsend building in the heart of Townsend, Montana, the Loft on Broadway is an updated space with old town charm. Built in 1910 and completely renovated in 2023, it boasts the original red brick walls inside the apartment and a central downtown location. With each booking we include a $25 gift card to Deep Creek Pizza, conveniently located just below the Loft! Two bedrooms, two bathrooms and an open kitchen and living area make this place a gem!

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.

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.