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Winston Vacation Rentals

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Winston vacation rentals

Exterior detail

1. Rustic cabin with lake views.

Rustic cabin with lake views.
Townsend
9.6 out of 10, Exceptional, (43 reviews)
"Great location away from everything - nice view of the lake. We enjoyed the fresh air. Very clean!"
United States
Brett
The price is ￥15,740
￥20,399 total
includes taxes & fees
Sep 1 - Sep 2
Rustic cabin with lake views.
Exterior

2. Ranch House in the Elkhorn Mountains

Ranch House in the Elkhorn Mountains
Clancy
9.8 out of 10, Exceptional, (126 reviews)
"Great remote location with views. Pet friendly & cozy!"
United States
Holly G.
The price is ￥22,823
￥28,389 total
includes taxes & fees
Sep 1 - Sep 2
Ranch House in the Elkhorn Mountains
Exterior

3. Lee's apartment building on saddle mountain

Lee's apartment building on saddle mountain
Clancy
10.0 out of 10, Exceptional, (66 reviews)
"Very nice stay"
United States
Randy N.
The price is ￥19,675
￥36,038 total
includes taxes & fees
Aug 30 - Aug 31
Lee's apartment building on saddle mountain
Outdoor dining

4. SADDLE MOUNTAIN ESCAPE

SADDLE MOUNTAIN ESCAPE
Clancy
9.8 out of 10, Exceptional, (40 reviews)
"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 ￥21,249
￥40,798 total
includes taxes & fees
Aug 7 - Aug 8
SADDLE MOUNTAIN ESCAPE
Coffee/tea maker, fridge, microwave, oven

5. Cozy townhouse close to Hospital & Capital

Cozy townhouse close to Hospital & Capital
Helena
10.0 out of 10, Exceptional, (110 reviews)
"Perfect stay!"
United States
Craig R.
The price is ￥18,674
￥35,854 total
includes taxes & fees
Aug 4 - Aug 5
Cozy townhouse close to Hospital & Capital
Exterior

6. Cozy Cabin

Cozy Cabin
Clancy
8.8 out of 10, Excellent, (37 reviews)
"Was really quiet and very enjoyable!"
United States
Kaylee N.
The price is ￥21,249
￥33,148 total
includes taxes & fees
Aug 9 - Aug 10
Cozy Cabin
Property grounds

7. 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, (202 reviews)
"It was a very enjoyable stay"
United States
Matthias A.
The price is ￥20,462
￥25,499 total
includes taxes & fees
Aug 4 - Aug 5
Tizer Botanic Gardens Cabin 1/2 way between Yellowstone & Glacier National Parks
Smart TV

8. Lee's Helena Hideout

Lee's Helena Hideout
Helena
10.0 out of 10, Exceptional, (44 reviews)
"Clean and the host was great! Very nice place close to the hospital."
United States
Kara D.
The price is ￥19,124
￥38,163 total
includes taxes & fees
Aug 4 - Aug 5
Lee's Helena Hideout
Terrace/patio

9. Spacious artist's studio loft apartment with view

Spacious artist's studio loft apartment with view
Helena
9.8 out of 10, Exceptional, (10 reviews)
"We enjoyed this "
United States
Mary L.
The price is ￥16,999
￥40,458 total
includes taxes & fees
Aug 30 - Aug 31
Spacious artist's studio loft apartment with view
Exterior

10. 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.
The price is ￥19,831
￥25,666 total
includes taxes & fees
Aug 30 - Aug 31
Cabin 22 - The Movie Cabin
Dining

11. 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, (75 reviews)
"Perfect fit for our family trip to Helena! "
United States
Katie W.
The price is ￥30,166
￥37,234 total
includes taxes & fees
Aug 5 - Aug 6
Style and comfort in Helena! Easy access to any part of Helena. No cleaning fees
Interior

12. 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, (7 reviews)
"Great place to stay. "
United States
Mark N.
Trails, Tails & Town – Pet-Friendly Stay Near It All
Exterior

13. 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, (81 reviews)
"It was a perfect weekend away from home. I would stay again. "
United States
Crystal A.
The price is ￥23,610
￥35,018 total
includes taxes & fees
Aug 29 - Aug 30
Helena Townhouse next to Skelton Park (Dog and kid friendly)
Exterior

14. 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 ￥19,831
￥25,666 total
includes taxes & fees
Aug 30 - Aug 31
Suite 33 - Queen Suite W/ Walk-In Shower
Outdoor dining

15. Apartment next to Cathedral in Historic Downtown Helena

Apartment next to Cathedral in Historic Downtown Helena
Helena
9.0 out of 10, Wonderful, (41 reviews)
"Very convenient location. Easy to walk everywhere downtown."
United States
Keith
The price is ￥21,249
￥40,798 total
includes taxes & fees
Sep 1 - Sep 2
Apartment next to Cathedral in Historic Downtown Helena
Private kitchen

16. LOVELY 2 Bedroom Fully Furnished w/ Laundry

LOVELY 2 Bedroom Fully Furnished w/ Laundry
Helena
10.0 out of 10, Exceptional, (11 reviews)
"Convenient, nice, close to town place."
United States
Jessica S.
The price is ￥21,674
￥46,017 total
includes taxes & fees
Aug 31 - Sep 1
LOVELY 2 Bedroom Fully Furnished w/ Laundry
Private kitchen

17. PERFECT 2 bedroom, 1 bath Condo

PERFECT 2 bedroom, 1 bath Condo
Helena
9.8 out of 10, Exceptional, (40 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 ￥21,816
￥46,169 total
includes taxes & fees
Aug 31 - Sep 1
PERFECT 2 bedroom, 1 bath Condo
Exterior

18. Suites 35 +Up - Victorian Queen

Suites 35 +Up - Victorian Queen
Helena
9.4 out of 10, Exceptional, (9 reviews)
"Thank you for a great stay- the location was perfect as we were in town for the governors cup race. Enjoyed my morning coffee in the sunroom. Comfy beds & plenty of pillows & towels. "
United States
Tiffany K.
The price is ￥19,831
￥25,666 total
includes taxes & fees
Aug 30 - Aug 31
Suites 35 +Up - Victorian Queen
Exterior

19. 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.
The price is ￥24,100
￥30,853 total
includes taxes & fees
Aug 3 - Aug 4
Cabin 26 - Coyboy Corner
Interior

20. Find Your Sanctuary at The Church

Find Your Sanctuary at The Church
Helena
10.0 out of 10, Exceptional, (13 reviews)
"Great stay"
United States
David Y.
The price is ￥32,897
￥69,357 total
includes taxes & fees
Aug 31 - Sep 1
Find Your Sanctuary at The Church
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.
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Top Winston Hotel Reviews

Lamplighter Cabins & Suites

Lamplighter Cabins & Suites

8/10 Good
"We stayed one"
SASHA 1-night trip
Posted 1 hour ago
Lamplighter Cabins & Suites

Find out more about Winston

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

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?

Cozy spacious king bed suite, In the heart of Historic Helena, Montana!: This vacation home rental outside of Winston is located in the mountains and has a fireplace, a selection of books, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave, and a coffee maker.

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.