Winston Holiday Rentals

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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Winston holiday rentals

1 bedroom, WiFi, bed sheets
Mountain Silo #7

Cabin in Townsend

Mountain Silo #7
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful property and a true escape into the heart of Montana. What a wonderful place for us to celebrate our 30th anniversary. Thank you!!!!"
United States
Sheila E.
The price is HK$1,676
HK$2,988 total
includes taxes & fees
14 Jan - 15 Jan
Mountain Silo #7
Interior
Adorable 2-bedroom cottage in wonderful Helena for a quiet and relaxing stay.

Cottage in Helena

Adorable 2-bedroom cottage in wonderful Helena for a quiet and relaxing stay.
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"This sweet lodging was very clean, comfortable and just as described in the website. It is a very quiet neighborhood. The hostess was quick to respond to questions, being attentive and available. I would highly recommend this place for a small group or individual staying in Helena."
United States
Tom R.
The price is HK$543
HK$1,175 total
includes taxes & fees
13 Jan - 14 Jan
Adorable 2-bedroom cottage in wonderful Helena for a quiet and relaxing stay.
Property grounds
Cozy cabin nestled beside a spring-fed pond&hobby farm in the Elkhorn Mountains

Cabin in East Helena

Cozy cabin nestled beside a spring-fed pond&hobby farm in the Elkhorn Mountains
10.0 out of 10, Exceptional, (21 reviews)
"Very cute cabin and property. Enjoyed our time."
United States
Amanda F.
The price is HK$1,559
HK$3,081 total
includes taxes & fees
14 Jan - 15 Jan
Cozy cabin nestled beside a spring-fed pond&hobby farm in the Elkhorn Mountains
Interior
Mountain Sio #6

Cabin in Townsend

Mountain Sio #6
10.0 out of 10, Exceptional, (1 review)
"Location awesome and clean cabin "
United States
Meghan J.
The price is HK$1,754
HK$3,081 total
includes taxes & fees
14 Jan - 15 Jan
Mountain Sio #6
Fridge, microwave, oven, stovetop
Cozy townhouse close to Hospital & Capital

Holiday Home in Helena

Cozy townhouse close to Hospital & Capital
10.0 out of 10, Exceptional, (96 reviews)
"Perfect stay!"
United States
Craig R.
The price is HK$807
HK$1,621 total
includes taxes & fees
13 Jan - 14 Jan
Cozy townhouse close to Hospital & Capital
Exterior
Cabin 22 - The Movie Cabin

Cabin in Helena

Cabin 22 - The Movie Cabin
9.0 out of 10, Wonderful, (2 reviews)
"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 HK$499
HK$741 total
includes taxes & fees
14 Jan - 15 Jan
Cabin 22 - The Movie Cabin
1 bedroom, WiFi
Suite 30 - Double Queen Corner Suite

Aparthotel in Helena

Suite 30 - Double Queen Corner Suite
9.0 out of 10, Wonderful, (6 reviews)
"Perfect location and easily accessible."
United States
Shayna B.
The price is HK$514
HK$758 total
includes taxes & fees
13 Jan - 14 Jan
Suite 30 - Double Queen Corner Suite
Exterior
Lee's apartment building on saddle mountain

Cabin in Clancy

Lee's apartment building on saddle mountain
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 HK$974
HK$1,785 total
includes taxes & fees
13 Jan - 14 Jan
Lee's apartment building on saddle mountain
Dining
Great place to crash after a Montana adventure!

Apartment in East Helena

Great place to crash after a Montana adventure!
2.0 star property
The price is HK$405
HK$631 total
includes taxes & fees
13 Jan - 14 Jan
Great place to crash after a Montana adventure!
Outdoor dining
SADDLE MOUNTAIN ESCAPE

Apartment in Clancy

SADDLE MOUNTAIN ESCAPE
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 HK$1,052
HK$2,020 total
includes taxes & fees
13 Jan - 14 Jan
SADDLE MOUNTAIN ESCAPE
Exterior
Suites 35 +Up - Victorian Queen

Holiday Home in Helena

Suites 35 +Up - Victorian Queen
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 HK$499
HK$741 total
includes taxes & fees
14 Jan - 15 Jan
Suites 35 +Up - Victorian Queen
3 bedrooms, WiFi
This cozy house has been completely remodeled inside and features three bedrooms.

Holiday Home in Helena

This cozy house has been completely remodeled inside and features three bedrooms.
2.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"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 HK$974
HK$1,254 total
includes taxes & fees
20 Jan - 21 Jan
This cozy house has been completely remodeled inside and features three bedrooms.
Terrace/patio
Spacious artist's studio loft apartment with view

Apartment in Helena

Spacious artist's studio loft apartment with view
9.8 out of 10, Exceptional, (8 reviews)
"We enjoyed this "
United States
Mary L.
The price is HK$702
HK$1,642 total
includes taxes & fees
17 Jan - 18 Jan
Spacious artist's studio loft apartment with view
Property grounds
Tizer Botanic Gardens Cabin 1/2 way between Yellowstone & Glacier National Parks

Cabin in Jefferson City

Tizer Botanic Gardens Cabin 1/2 way between Yellowstone & Glacier National Parks
10.0 out of 10, Exceptional, (192 reviews)
"It was a very enjoyable stay"
United States
Matthias A.
The price is HK$1,013
HK$1,263 total
includes taxes & fees
31 Jan - 1 Feb
Tizer Botanic Gardens Cabin 1/2 way between Yellowstone & Glacier National Parks
Exterior
Helena Townhouse next to Skelton Park (Dog and kid friendly)

Holiday Home in Helena

Helena Townhouse next to Skelton Park (Dog and kid friendly)
10.0 out of 10, Exceptional, (57 reviews)
"Nice property, great price, great location "
United States
Joan J.
The price is HK$877
HK$1,376 total
includes taxes & fees
25 Jan - 26 Jan
Helena Townhouse next to Skelton Park (Dog and kid friendly)
2 bedrooms, WiFi, bed sheets
Giant View Home

Holiday Home in Helena

Giant View Home
10.0 out of 10, Exceptional, (16 reviews)
"Great views. Perfect location for working and playing in/around Helena. I will book this place the next time we get to go to Montana."
United States
John T.
The price is HK$935
HK$2,071 total
includes taxes & fees
1 Feb - 2 Feb
Giant View Home
Private kitchen
PERFECT 2 bedroom, 1 bath Condo

Condo in Helena

PERFECT 2 bedroom, 1 bath Condo
9.6 out of 10, Exceptional, (28 reviews)
"The place was very clean and had all the amenities needed. "
United States
Carlos O.
The price is HK$1,179
HK$2,418 total
includes taxes & fees
13 Jan - 14 Jan
PERFECT 2 bedroom, 1 bath Condo
Interior
Trails, Tails & Town – Pet-Friendly Stay Near It All

Apartment in Helena

Trails, Tails & Town – Pet-Friendly Stay Near It All
10.0 out of 10, Exceptional, (2 reviews)
"Awesome great place!"
United States
Valarie S.
The price is HK$723
HK$949 total
includes taxes & fees
18 Jan - 19 Jan
Trails, Tails & Town – Pet-Friendly Stay Near It All
Dining
Style and comfort in Helena! Easy access to any part of Helena. No cleaning fees

Holiday Home in Helena

Style and comfort in Helena! Easy access to any part of Helena. No cleaning fees
10.0 out of 10, Exceptional, (54 reviews)
"We enjoyed our stay. It was clean, cozy, well-appointed and had everything we needed. I would certainly stay there again. "
United States
Laura A.
The price is HK$1,368
HK$1,679 total
includes taxes & fees
18 Jan - 19 Jan
Style and comfort in Helena! Easy access to any part of Helena. No cleaning fees
Interior
Find Your Sanctuary at The Church

Holiday Home in Helena

Find Your Sanctuary at The Church
2.0 star property
10.0 out of 10, Exceptional, (10 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 HK$1,629
HK$3,451 total
includes taxes & fees
15 Jan - 16 Jan
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

10/10 Excellent
"Great, clean, convenient little spot."
Randall 2-night trip
Posted 3 days 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 holiday rentals in Winston?

Yes, there are holiday rentals close to the most popular sights in Winston, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winston has to offer?

Cozy townhouse close to Hospital & Capital: This holiday home rental outside of Winston offers a patio, a garden and air conditioning 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 wider area, you’ll find Canyon Ferry Wildlife Management Area and Hauser Dam.

What are holiday rentals like in Winston?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winston. Holiday rentals offer amenities like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for a small group gathering.