Winston Vacation Rentals

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Check prices for these dates

In two weeks
May 1 - May 3
In two months
Jun 12 - Jun 14
In three months
Jul 10 - Jul 12
In four months
Aug 7 - Aug 9

Our top choices for Winston vacation rentals

Exterior

Ranch House in the Elkhorn Mountains

Ranch House in the Elkhorn Mountains
Clancy
10.0 out of 10, Exceptional, (117 reviews)
"Great remote location with views. Pet friendly & cozy!"
United States
Holly G.
The price is ￥21,443
￥26,761 total
includes taxes & fees
Apr 23 - Apr 24
Ranch House in the Elkhorn Mountains
Exterior

Lee's apartment building on saddle mountain

Lee's apartment building on saddle mountain
Clancy
10.0 out of 10, Exceptional, (64 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 ￥19,855
￥36,368 total
includes taxes & fees
Apr 22 - Apr 23
Lee's apartment building on saddle mountain
Fridge, microwave, oven, stovetop

Cozy townhouse close to Hospital & Capital

Cozy townhouse close to Hospital & Capital
Helena
10.0 out of 10, Exceptional, (103 reviews)
"Perfect stay!"
United States
Craig R.
The price is ￥16,440
￥33,023 total
includes taxes & fees
Apr 27 - Apr 28
Cozy townhouse close to Hospital & Capital
Exterior

Luxury Home with Movie Room - right outside of Helena

Luxury Home with Movie Room - right outside of Helena
Clancy
10.0 out of 10, Exceptional, (3 reviews)
"Very clean, easy to find, peaceful environment, beautiful home. "
United States
Taylor O.
The price is ￥35,900
￥44,433 total
includes taxes & fees
May 17 - May 18
Luxury Home with Movie Room - right outside of Helena
Outdoor dining

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 ￥21,445
￥41,174 total
includes taxes & fees
Apr 30 - May 1
SADDLE MOUNTAIN ESCAPE
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, (64 reviews)
"Very nice place, look even better in real life."
United States
gage h.
The price is ￥30,021
￥37,054 total
includes taxes & fees
Apr 27 - Apr 28
Style and comfort in Helena! Easy access to any part of Helena. No cleaning fees
Smart TV

Lee's Helena Hideout

Lee's Helena Hideout
Helena
9.8 out of 10, Exceptional, (39 reviews)
"Had a great stay with all the comforts of home!"
United States
amy m.
The price is ￥19,300
￥38,343 total
includes taxes & fees
Apr 17 - Apr 18
Lee's Helena Hideout
Private kitchen

PERFECT 2 bedroom, 1 bath Condo

PERFECT 2 bedroom, 1 bath Condo
Helena
9.6 out of 10, Exceptional, (31 reviews)
"Great place definitely recommend for larger groups! Very clean and in a good neighborhood. Owner was very communicative and friendly. "
United States
Alyssa H.
The price is ￥24,017
￥49,269 total
includes taxes & fees
Apr 19 - Apr 20
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, (12 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 ￥33,198
￥69,992 total
includes taxes & fees
Apr 17 - Apr 18
Find Your Sanctuary at The Church
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 ￥21,445
￥33,454 total
includes taxes & fees
Apr 30 - May 1
Cozy Cabin
Exterior

Suite 32 - King Suite

Suite 32 - King Suite
Helena
9.6 out of 10, Exceptional, (18 reviews)
"Nice place to stay that avoids the hotel vibe."
United States
Erik
The price is ￥18,424
￥24,185 total
includes taxes & fees
Apr 20 - Apr 21
Suite 32 - King Suite
2 bedrooms, WiFi, bed sheets

Giant View Home

Giant View Home
Helena
10.0 out of 10, Exceptional, (18 reviews)
"Convenient but tucked away location, so many windows made it beautiful in the snow!"
United States
Lorien G.
The price is ￥19,061
￥48,033 total
includes taxes & fees
Apr 21 - Apr 22
Giant View Home
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 ￥26,685
￥52,665 total
includes taxes & fees
May 3 - May 4
LOVELY 2 Bedroom Fully Furnished w/ Laundry
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, (34 reviews)
"Great place to stay that is right next to downtown! It was very clean when we arrived! Overall, great place to stay!"
United States
Braden P.
The price is ￥18,267
￥37,226 total
includes taxes & fees
Apr 21 - Apr 22
Apartment next to Cathedral in Historic Downtown Helena
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, (71 reviews)
"Enjoyed my stay, very pet friendly. "
United States
Linda S.
The price is ￥14,154
￥23,863 total
includes taxes & fees
Apr 27 - Apr 28
Helena Townhouse next to Skelton Park (Dog and kid friendly)
2 bedrooms, WiFi

Cabin 25 - The Ski Lodge

Cabin 25 - The Ski Lodge
Helena
8.8 out of 10, Excellent, (6 reviews)
"Location and friendliness"
United States
Isidor R.
The price is ￥18,424
￥24,185 total
includes taxes & fees
Apr 21 - Apr 22
Cabin 25 - The Ski Lodge
Outdoor dining

Nestled in the National Forest, just minutes from downtown

Nestled in the National Forest, just minutes from downtown
Helena
9.6 out of 10, Exceptional, (17 reviews)
"Beautiful location, scenery"
United States
Rhonda H.
The price is ￥35,977
￥73,851 total
includes taxes & fees
Apr 19 - Apr 20
Nestled in the National Forest, just minutes from downtown
Interior

South Hills - Sleeps 12+ - Sauna, Gym, Air Hockey

South Hills - Sleeps 12+ - Sauna, Gym, Air Hockey
Helena
South Hills - Sleeps 12+ - Sauna, Gym, Air Hockey
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)
"Awesome great place!"
United States
Valarie S.
The price is ￥26,369
￥32,596 total
includes taxes & fees
May 16 - May 17
Trails, Tails & Town – Pet-Friendly Stay Near It All
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.
The price is ￥18,424
￥24,185 total
includes taxes & fees
Apr 20 - Apr 21
Cabin 26 - Coyboy Corner
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

10/10 Excellent
"Specific parking for the unit. We didnt use anything it kitchen but it looked like had all one would need!! Nice open room. Large bathroon Staff very friendly. "
Kristina 1-night trip
Posted 9 hours ago
Lamplighter Cabins & Suites

Find out more about Winston

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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 Montana State Capitol.

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.