Vacation rentals 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.

Elegant Downtown Studio #3, No Cleaning Fee!

Come stay at the newly updated studio. In the Historic Parchen Building located in the heart of Downtown Helena. Sleeps up to 3 guests with a lovely double daybed complete with luxury bedding and a rollout twin trundle bed. Fully stocked kitchen for your meals in. Dine in or take dinner from Helena's best restaurant On Broadway located just below your studio. There is paid parking in the many lots around the building. As well as free 1 and 2 hour spaces and free over night and weekend parkin.

"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!

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?

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.