Winston Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    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

Tonight
Oct 23 - Oct 24
Tomorrow
Oct 24 - Oct 25
This weekend
Oct 24 - Oct 26
Next weekend
Oct 31 - Nov 2

Vacation Rentals in Winston

Exterior detail
Rustic cabin with lake views.
Rustic cabin with lake views.
9.6 out of 10, Exceptional, (39)
"The host Beth was very helpful!"
United States
Jerilynn
The price is ￥15,191
￥19,688 total
includes taxes & fees
Oct 30 - Oct 31
Rustic cabin with lake views.
1 bedroom, WiFi, bed sheets
Mountain Silo #7
Mountain Silo #7
10.0 out of 10, Exceptional, (5)
"This listing is 100% as advertised. Tina is a most gracious host and her attention to detail in and around the Silo is amazing. As my daughter said, "The character and design of the Silo is unmatched by any other place I've ever stayed. Every detail is just perfect!". Here are just a few examples of how Tina and her Silo are both worth visiting: 1. The vistas are amazing at all hours of the day, there were so many stars. 2. Tina provides suggestions of where you can explore. 3. You could bring...
United States
Shannon K.
The price is ￥32,661
￥60,047 total
includes taxes & fees
Oct 25 - Oct 26
Mountain Silo #7
1 bedroom, WiFi, bed sheets
Mountain Sio #6
Mountain Sio #6
10.0 out of 10, Exceptional, (1)
"Location awesome and clean cabin "
United States
Meghan J.
The price is ￥34,180
￥61,032 total
includes taxes & fees
Oct 25 - Oct 26
Mountain Sio #6
Interior
Cozy cabin nestled beside a spring-fed pond&hobby farm in the Elkhorn Mountains
Cozy cabin nestled beside a spring-fed pond&hobby farm in the Elkhorn Mountains
10.0 out of 10, Exceptional, (21)
"Great cozy cabin with wonderful serene setting. "
United States
Joseph S.
The price is ￥30,382
￥60,703 total
includes taxes & fees
Oct 31 - Nov 1
Cozy cabin nestled beside a spring-fed pond&hobby farm in the Elkhorn Mountains
Interior
Ranch House in the Elkhorn Mountains
Ranch House in the Elkhorn Mountains
10.0 out of 10, Exceptional, (116)
"Beautiful views, great hosts, serene and peaceful. "
United States
darlene h.
The price is ￥18,989
￥23,953 total
includes taxes & fees
Nov 1 - Nov 2
Ranch House in the Elkhorn Mountains
Interior
Lee's apartment building on saddle mountain
Lee's apartment building on saddle mountain
10.0 out of 10, Exceptional, (64)
"Great little cabin. We had everything we needed and was comfortable and clean. My son loved the loft area! Great communication with Hosts. We would definitely stay here again. "
United States
Lori V.
The price is ￥18,989
￥34,782 total
includes taxes & fees
Oct 25 - Oct 26
Lee's apartment building on saddle mountain
Fridge, microwave, oven, stovetop
Cozy townhouse close to Hospital & Capital
Cozy townhouse close to Hospital & Capital
10.0 out of 10, Exceptional, (92)
"We really enjoyed our time the home was very cozy and in the perfect location "
United States
Ashley B.
The price is ￥15,723
￥28,793 total
includes taxes & fees
Oct 29 - Oct 30
Cozy townhouse close to Hospital & Capital
Outdoor dining
SADDLE MOUNTAIN ESCAPE
SADDLE MOUNTAIN ESCAPE
9.8 out of 10, Exceptional, (40)
"The apartment was a perfect space for our family weekend in Montana City. They apartment had everything and more, and would be great for a week long stay if we had more time. Friendly host and beautiful location!"
United States
Melani V.
The price is ￥20,508
￥39,375 total
includes taxes & fees
Oct 31 - Nov 1
SADDLE MOUNTAIN ESCAPE
Exterior
Cabin 22 - The Movie Cabin
Cabin 22 - The Movie Cabin
10.0 out of 10, Exceptional, (1)
"Cute and clean cabins in Helena - the Movie Cabin is a nod to Myrna Loy and Gary Cooper, which are fun touches. Cabin 22 is very compact and clean. The mini fridge was a plus. "
United States
Angela H.
The price is ￥11,544
￥16,405 total
includes taxes & fees
Oct 26 - Oct 27
Cabin 22 - The Movie Cabin
Exterior
Suite 32 - King Suite
Suite 32 - King Suite
9.8 out of 10, Exceptional, (16)
"Nice place to stay that avoids the hotel vibe."
United States
Erik
The price is ￥15,189
￥20,342 total
includes taxes & fees
Oct 26 - Oct 27
Suite 32 - King Suite
Terrace/patio
Spacious artist's studio loft apartment with view
Spacious artist's studio loft apartment with view
9.8 out of 10, Exceptional, (8)
"Great place for some peace, rest and quiet celebration for the runners in our group as well as the supporters. Great location close to town and adjacent to trail access. Well appointed kitchen and nice views."
United States
Betsy O.
The price is ￥12,396
￥30,285 total
includes taxes & fees
Oct 26 - Oct 27
Spacious artist's studio loft apartment with view
Exterior detail
Cabin 26 - Coyboy Corner
Cabin 26 - Coyboy Corner
8.0 out of 10, Very Good, (1)
"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.
The price is ￥11,544
￥16,405 total
includes taxes & fees
Oct 29 - Oct 30
Cabin 26 - Coyboy Corner
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
10.0 out of 10, Exceptional, (192)
"We had a great time. "
United States
Laura
The price is ￥19,748
￥24,609 total
includes taxes & fees
Oct 31 - Nov 1
Tizer Botanic Gardens Cabin 1/2 way between Yellowstone & Glacier National Parks
Fridge, microwave, oven, stovetop
Helena Townhouse next to Skelton Park (Dog and kid friendly)
Helena Townhouse next to Skelton Park (Dog and kid friendly)
10.0 out of 10, Exceptional, (51)
"Clean, comfortable, convenient. Thanks!"
United States
caleb
The price is ￥21,115
￥31,664 total
includes taxes & fees
Nov 21 - Nov 22
Helena Townhouse next to Skelton Park (Dog and kid friendly)
Exterior
Suite 34- Victorian Suite
Suite 34- Victorian Suite
7.4 out of 10, Good, (6)
"Overall we had a good time. Didn't have any issues with our stay. "
United States
Lisa R.
The price is ￥11,544
￥16,405 total
includes taxes & fees
Oct 26 - Oct 27
Suite 34- Victorian Suite
Eco-friendly cleaning products, paper towels, dining tables
Giant View Home
Giant View Home
10.0 out of 10, Exceptional, (13)
"Loved my stay and would absolutely book again when I visit Helena next. Everything about the house and property were great, and the location is nice and quiet. "
United States
Ethan K.
The price is ￥17,318
￥39,211 total
includes taxes & fees
Oct 29 - Oct 30
Giant View Home
Private kitchen
BRAND NEW 2 Bedroom, 1 Bathroom Condo
BRAND NEW 2 Bedroom, 1 Bathroom Condo
9.8 out of 10, Exceptional, (7)
"The property was cleaned, had what we needed, newer construction right on the edge of Helena. Fit our needs perfectly! Would stay again."
United States
Christopher & Keshia F.
The price is ￥22,969
￥47,120 total
includes taxes & fees
Nov 6 - Nov 7
BRAND NEW 2 Bedroom, 1 Bathroom Condo
Private kitchen
LOVELY 2 Bedroom Fully Furnished w/ Laundry
LOVELY 2 Bedroom Fully Furnished w/ Laundry
10.0 out of 10, Exceptional, (6)
"Convenient, nice, close to town place."
United States
Jessica S.
The price is ￥22,969
￥47,120 total
includes taxes & fees
Oct 25 - Oct 26
LOVELY 2 Bedroom Fully Furnished w/ Laundry
Fridge, microwave, oven, stovetop
This cozy house has been completely remodeled inside and features three bedrooms.
This cozy house has been completely remodeled inside and features three bedrooms.
2.0 star property
10.0 out of 10, Exceptional, (2)
"The house was perfect for my family. Dogs had a fenced yard and the facilities were close to the college and golf course. "
United States
Scott O.
The price is ￥18,989
￥24,446 total
includes taxes & fees
Nov 3 - Nov 4
This cozy house has been completely remodeled inside and features three bedrooms.
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
10.0 out of 10, Exceptional, (50)
"Cozy and very clean. I would stay here again anytime!"
United States
Joelle H.
The price is ￥29,622
￥36,586 total
includes taxes & fees
Nov 9 - Nov 10
Style and comfort in Helena! Easy access to any part of Helena. No cleaning fees
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

Delta Hotels by Marriott Helena Colonial

Delta Hotels by Marriott Helena Colonial

10/10 Excellent
"Beautiful stairway in the lobby. Few steps up from the last place we stayed at in Helena. This is our new favorite. We’ll be back! "
Joy 1-night trip
Posted 3 days ago
Delta Hotels by Marriott Helena Colonial

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?

Helena Townhouse next to Skelton Park (Dog and kid friendly): This vacation home rental outside of Winston is located near skiing and has a fireplace, a garden, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

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 Hauser Dam.

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.