Vacation 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

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.

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.

King Studio with fireplace close to The Myrna Loy

The Cannon House set the stage for what Helena has become when built over 150 years ago. It’s Helena’s oldest grand home and this magnificent ground level Victorian jewel invites the past with the exquisite attention to today. It’s located only two minutes from Downtown, The Myrna Loy, the Cathedral and hiking and biking just up the street. Enjoy the fireplace that sets the mood with a touch of a button, and then get ready for a Helena experience like no other.

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.