Vacation rentals in Winston

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Top-rated vacation rentals in Winston

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Guest favorite

Home in Helena

4.96 out of 5 average rating, 128 reviews

Cheerful 1 Bedroom Luxurious Suite w/Hot Tub!

The Lillie Pad Awaits Your Arrival... Come home to your Ultimate, Mountaintop Luxury Glamping-Suite w/ oversized hot tub - Majestic Mile High Ranch beauty at its best! Total seclusion with world class views of the rocky mountain front and continental divide, only minutes from Montana's Capital. Meticulously handcrafted in the center of the CanyonRidge Ranch, which borders the immense Helena National Forest & lush mountain meadows... Makes the Lillie Pad a truly one-of-a-kind experience and stay!

Nov 1 – 8

G$81,939 GYD per night

Guest favorite

Apartment in Helena

4.86 out of 5 average rating, 108 reviews

Elegant Downtown Studio

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.

Jan 30 – Feb 6

G$24,495 GYD per night

Guest favorite

Cottage in Three Forks

4.97 out of 5 average rating, 135 reviews

Cozy, clean, comfortable. In town with zero chores

This historic cottage of fly fishing Godfather Bud Lilly. Locally-owned and maintained by his son, Chris, the nostalgic Retreat is a rustic 1BR 1 BA with full kitchen, dining, and living room that sleeps three. NO CLEANING FEE and NO CHORES here. Central Three Forks location-you are minutes from fine dining, blue-ribbon trout streams, world-class ski hills, and Yellowstone Park. Perfect for couples and small families looking for home comforts under the Big Sky. Convenient, cozy, comfortable.

Jan 27 – Feb 3

G$26,624 GYD per night

Guest favorite

Apartment in Townsend

4.91 out of 5 average rating, 92 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.

Feb 17 – 24

G$12,415 GYD per night

Guest favorite

Cabin in East Helena

4.95 out of 5 average rating, 177 reviews

Tiny Cabin- 2 sleeping lofts. Between town & lake

A homey cabin located in East Helena. Just 10 miles from Helena and 5 miles to Canyon Ferry lake. We are excited to welcome guests who are passing through or those who hope to stay for a while. Enjoy coffee in the mornings on the front porch with a relaxing view of our little pond. Our fully equipped kitchen will help you stay fueled for all Montana adventures. With two sleeping lofts and a pull out sofa there’s plenty of room for the whole family or keep it intimate for a couples get away.

Jul 26 – Aug 2

G$28,822 GYD per night

Guest favorite

Guest suite in Helena

5.0 out of 5 average rating, 444 reviews

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.

Nov 24 – Dec 1

G$22,741 GYD per night

Guest favorite

Farm stay in Clancy

4.86 out of 5 average rating, 77 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.

Nov 6 – 13

G$22,409 GYD per night

Guest favorite

Chalet in Helena

4.98 out of 5 average rating, 211 reviews

Black Mountain Chalet

Nestled in the Aspens, a stones throw away from Colorado Creek, is where you will find the Chalet. Thoughtful touches and ample amenities, ensure guests will experience an enchanted getaway. The surrounding meadows and forested areas offer hiking and a range of flora/fauna viewing opportunities. We invite you to experience the tranquility of this private wonderland setting located close to Helena, Broadwater Hot Springs and The Wassweiler Dinner House and Pub.

Feb 21 – 28

G$32,323 GYD per night

Guest favorite

Cabin in Monarch

4.96 out of 5 average rating, 130 reviews

Sun Mountain Cabin

Our Cabin is located just outside of Monarch, Montana. You will find many activities to do in the area such as hunt, hike, ski, 4 wheel, raft, kayak, and fish are just a small list of the possibilities that await you. It's also the perfect getaway as cell service is very limited. Our cabin is perfect for couples, solo adventures and your furry friends, however there is a hide a bed couch that folds out if you need extra sleeping room.

Feb 22 – Mar 1

G$26,457 GYD per night

Guest favorite

Condo in Townsend

5.0 out of 5 average rating, 11 reviews

Townsend Penthouse

Enjoy small-town luxury in Townsend with our chic 2-bed, 2-bath condo featuring leather couches, velvet accents, arcade games, and a fully stocked kitchen. The living room offers extra sleeping space with a pull-out couch. This building from early 1900s offers tons of unique charm and has been fully remodeled. Great views, full of sunlight and located downtown Townsend. You can be fully entertained without ever leaving!

Jun 3 – 10

G$25,397 GYD per night

Guest favorite

Earthen home in Clancy

4.93 out of 5 average rating, 283 reviews

The Hideaway at Creekside Meadows-Hobbit House

Nestled in the foothills of the Elkhorn Mountains you’ll find our charming earth home. Clean Scandinavian style decor allows the magnificent construction of this home to shine. A few unique features include 4 full sized built in sleeping nooks each with their own lights and electrical outlets, a secret door to a hidden private bedroom, and a shower you enter through a ‘tree trunk’ with almost 13ft ceilings!

Feb 17 – 24

G$62,553 GYD per night

Guest favorite

Home in Townsend

4.96 out of 5 average rating, 23 reviews

Lake access home we call Dads Den!

Welcome to Dads Den! Relax with the whole family at this beautiful lakeside home. Dads Den is 20 minutes away from East Helena and 1 hour away from Bozeman. It’s a peaceful area to bring the family to relax and unwind. You are a short little drive away from the main boat ramp where all sorts of adventures can arise. We hope you enjoy some rest and relaxation at Dads Den!

Jan 26 – Feb 2

G$44,496 GYD per night