Vacation rentals in Winston

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Top-rated vacation rentals in Winston

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Guest favorite

Apartment in Townsend

4.89 out of 5 average rating, 139 reviews

"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.

Guest favorite

Apartment in Helena

4.94 out of 5 average rating, 270 reviews

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

Guest favorite

Condo in Helena

4.93 out of 5 average rating, 258 reviews

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!

Guest favorite

Farm stay in Clancy

4.85 out of 5 average rating, 111 reviews

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.

Guest favorite

Apartment in Helena

4.9 out of 5 average rating, 103 reviews

Mount Helena Mainstay-Close to Trails

This property is located along a busy street. We provide fans, noise machines, and earplugs for your comfort! Enjoy a stay close to Carroll College, trails, shopping, restaurants, and everything Helena offers. You can find everything you need right here with keyless entry, wi-fi, a storage shed for your outdoor gear, and plenty of amenities. This property offers two memory foam queen beds, a pull-out full bed, Made in Montana products, and a fully stocked kitchen and bathroom.

Guest favorite

Home in Helena

4.96 out of 5 average rating, 135 reviews

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.

Top guest favorite

Cabin in Jefferson City

5 out of 5 average rating, 122 reviews

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.

Top guest favorite

Home in Helena

4.99 out of 5 average rating, 114 reviews

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!

Guest favorite

Guesthouse in Townsend

4.92 out of 5 average rating, 24 reviews

Canyon Ferry Cottage

Relax with the whole family at this peaceful place to stay with views of Canyon Ferry Lake and the Elkhorn and Big Belt Mountains. The guesthouse features 2 bedrooms and 1 bathroom. Room 1 features a queen size bed. Room 2 has a bunk bed with full size bed on the bottom and twin on top. The bathroom features a walk-in tile shower. This is the perfect location to enjoy the Helena-Townsend area including Canyon Ferry Lake!

Guest favorite

Cabin in Toston

4.91 out of 5 average rating, 120 reviews

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. Road to cabin is dirt road may not be suitable for very low profile cars.

Guest favorite

Cabin in Clancy

4.93 out of 5 average rating, 130 reviews

Secluded Cabins surrounded by National Forest 1

2 NIGHT MINIMUM REQUIRED / pets allowed with approval. All dogs ae required to be on a leash and under supervision when on the property. 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...

Guest favorite

Cabin in Boulder

4.97 out of 5 average rating, 121 reviews

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.