Winston Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

Our top choices for Winston vacation rentals

Exterior detail

Rustic cabin with lake views.

Rustic cabin with lake views.
Townsend
9.6 out of 10, Exceptional, (40 reviews)
"This was a great cozy cabin with a wonderful view!"
United States
Josh N.
The price is ￥15,927
￥20,641 total
includes taxes & fees
Jun 8 - Jun 9
Rustic cabin with lake views.
Exterior

Lee's apartment building on saddle mountain

Lee's apartment building on saddle mountain
Clancy
10.0 out of 10, Exceptional, (65 reviews)
"So much thoughtful care was put into creating this bunkhouse retreat. We especially loved the friendly dogs that greeted us in the morning."
United States
Audrey H.
The price is ￥19,909
￥36,467 total
includes taxes & fees
Jun 2 - Jun 3
Lee's apartment building on saddle mountain
Exterior

Ranch House in the Elkhorn Mountains

Ranch House in the Elkhorn Mountains
Clancy
10.0 out of 10, Exceptional, (118 reviews)
"Great remote location with views. Pet friendly & cozy!"
United States
Holly G.
The price is ￥23,094
￥28,726 total
includes taxes & fees
Jun 2 - Jun 3
Ranch House in the Elkhorn Mountains
Fridge, microwave, oven, stovetop

Cozy townhouse close to Hospital & Capital

Cozy townhouse close to Hospital & Capital
Helena
10.0 out of 10, Exceptional, (107 reviews)
"Perfect stay!"
United States
Craig R.
The price is ￥20,227
￥37,842 total
includes taxes & fees
Jun 22 - Jun 23
Cozy townhouse close to Hospital & Capital
Smart TV

Lee's Helena Hideout

Lee's Helena Hideout
Helena
10.0 out of 10, Exceptional, (42 reviews)
"Had a great stay with all the comforts of home!"
United States
amy m.
The price is ￥19,351
￥38,444 total
includes taxes & fees
Jun 4 - Jun 5
Lee's Helena Hideout
Exterior

Cozy Cabin

Cozy Cabin
Clancy
9.0 out of 10, Wonderful, (31 reviews)
"Was really quiet and very enjoyable!"
United States
Kaylee N.
The price is ￥21,501
￥33,370 total
includes taxes & fees
Jun 14 - Jun 15
Cozy Cabin
Dining

Style and comfort in Helena! Easy access to any part of Helena. No cleaning fees

Style and comfort in Helena! Easy access to any part of Helena. No cleaning fees
Helena
10.0 out of 10, Exceptional, (68 reviews)
"It was clean, had everything we needed! "
United States
Jessica H.
The price is ￥33,447
￥41,111 total
includes taxes & fees
Jun 30 - Jul 1
Style and comfort in Helena! Easy access to any part of Helena. No cleaning fees
Interior

Trails, Tails & Town – Pet-Friendly Stay Near It All

Trails, Tails & Town – Pet-Friendly Stay Near It All
Helena
10.0 out of 10, Exceptional, (5 reviews)
"Great place to stay. "
United States
Mark N.
The price is ￥22,298
￥27,522 total
includes taxes & fees
Jun 16 - Jun 17
Trails, Tails & Town – Pet-Friendly Stay Near It All
Exterior

Helena Townhouse next to Skelton Park (Dog and kid friendly)

Helena Townhouse next to Skelton Park (Dog and kid friendly)
Helena
10.0 out of 10, Exceptional, (74 reviews)
"Enjoyed my stay, very pet friendly. "
United States
Linda S.
Helena Townhouse next to Skelton Park (Dog and kid friendly)
Property grounds

Tizer Botanic Gardens Cabin 1/2 way between Yellowstone & Glacier National Parks

Tizer Botanic Gardens Cabin 1/2 way between Yellowstone & Glacier National Parks
Jefferson City
10.0 out of 10, Exceptional, (193 reviews)
"It was a very enjoyable stay"
United States
Matthias A.
The price is ￥20,705
￥25,802 total
includes taxes & fees
Jun 2 - Jun 3
Tizer Botanic Gardens Cabin 1/2 way between Yellowstone & Glacier National Parks
Exterior

Cabin 22 - The Movie Cabin

Cabin 22 - The Movie Cabin
Helena
9.0 out of 10, Wonderful, (4 reviews)
"Nice affordable place"
United States
Jackie L.
Cabin 22 - The Movie Cabin
Private kitchen

PERFECT 2 bedroom, 1 bath Condo

PERFECT 2 bedroom, 1 bath Condo
Helena
9.6 out of 10, Exceptional, (33 reviews)
"We really loved the kitchen. The condo was very clean and modern. It was very comfortable and met all of our needs. "
United States
Coleen M.
The price is ￥24,655
￥50,192 total
includes taxes & fees
Jun 2 - Jun 3
PERFECT 2 bedroom, 1 bath Condo
Interior

Find Your Sanctuary at The Church

Find Your Sanctuary at The Church
Helena
10.0 out of 10, Exceptional, (13 reviews)
"It was a beautiful place to stay! The Neighborhood was great The location was so close to downtown The house looked just as the pictures did online! We didn't want to leave. "
United States
Wendy M.
The price is ￥33,287
￥70,524 total
includes taxes & fees
Jun 2 - Jun 3
Find Your Sanctuary at The Church
Terrace/patio

Spacious artist's studio loft apartment with view

Spacious artist's studio loft apartment with view
Helena
9.8 out of 10, Exceptional, (9 reviews)
"We enjoyed this "
United States
Mary L.
The price is ￥16,246
￥39,563 total
includes taxes & fees
Jun 14 - Jun 15
Spacious artist's studio loft apartment with view
Outdoor dining

Apartment next to Cathedral in Historic Downtown Helena

Apartment next to Cathedral in Historic Downtown Helena
Helena
9.0 out of 10, Wonderful, (35 reviews)
"We enjoyed our stay celebrating my daughter’s birthday. Very clean and cute interior design. Kids loved the air hockey table and games/toys. Thank you for the lovely stay!!"
United States
Alexandra E
The price is ￥27,872
￥49,195 total
includes taxes & fees
Jun 7 - Jun 8
Apartment next to Cathedral in Historic Downtown Helena
Private kitchen

LOVELY 2 Bedroom Fully Furnished w/ Laundry

LOVELY 2 Bedroom Fully Furnished w/ Laundry
Helena
10.0 out of 10, Exceptional, (7 reviews)
"Convenient, nice, close to town place."
United States
Jessica S.
The price is ￥23,508
￥48,781 total
includes taxes & fees
Jun 2 - Jun 3
LOVELY 2 Bedroom Fully Furnished w/ Laundry
Exterior

Cabin 26 - Coyboy Corner

Cabin 26 - Coyboy Corner
Helena
8.0 out of 10, Very Good, (1 review)
"Nice place would recommend. The only thing i wish they had was a better outside place to sit, maybe a patio set some where."
United States
Mark C.
Cabin 26 - Coyboy Corner
Exterior

Suite 33 - Queen Suite W/ Walk-In Shower

Suite 33 - Queen Suite W/ Walk-In Shower
Helena
9.8 out of 10, Exceptional, (7 reviews)
"This place is pretty great, and had been remodeled nicely. Perfect for a few days!"
United States
Jessica B.
The price is ￥31,852
￥40,419 total
includes taxes & fees
Jun 2 - Jun 3
Suite 33 - Queen Suite W/ Walk-In Shower
Exterior

Suite 34- Victorian Suite

Suite 34- Victorian Suite
Helena
7.4 out of 10, Good, (6 reviews)
"Safe, clean, had everything we needed! Conveniently located. "
United States
Melonie W.
The price is ￥31,852
￥40,419 total
includes taxes & fees
Jun 2 - Jun 3
Suite 34- Victorian Suite
Smart TV

Madison - newly remodeled, centrally located.

Madison - newly remodeled, centrally located.
Helena
9.4 out of 10, Exceptional, (13 reviews)
"We loved our stay here! "
United States
Jennifer B.
The price is ￥48,020
￥82,824 total
includes taxes & fees
Jun 10 - Jun 11
Madison - newly remodeled, centrally located.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winston Hotel Reviews

HELENA INN AIRPORT

HELENA INN AIRPORT

4/10 Poor
"We didn't stay after looking at location"
Cindy 1-night trip
Posted 1 hour ago
HELENA INN AIRPORT

Find out more about Winston

Search for holiday rentals in Winston on Expedia! You can easily find your home rentals, villas, holiday apartments in Winston using one of the methods below:

  • View our selection of featured holiday rentals in Winston
  • Use the map to find apartments and other holiday homes in the Winston neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winston while they last

Look no further and take a look at our great range of rental properties in Winston!

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Winston?

Yes, we give you a choice of vacation rentals close to popular sights in Winston, or you can select a more remote option if you'd like a relaxing place to stay.

What's the top vacation rental in Winston?

Style and comfort in Helena! Easy access to any part of Helena. No cleaning fees: This vacation home rental outside of Winston offers a garden, a selection of games, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What can I see and do in Winston?

Canyon Ferry Lake and Missouri River are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find Canyon Ferry Wildlife Management Area and Montana Historical Society Museum.

What are vacation rentals like in Winston?

Vacation rentals are privately owned properties you can reserve for a short or long stay in Winston. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for a small group gathering.