Winston Vacation Rentals

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Check prices for these dates

In two weeks
Feb 13 - Feb 15
In two months
Mar 27 - Mar 29
In three months
Apr 24 - Apr 26
In four months
May 22 - May 24

Our top choices for Winston vacation rentals

1 bedroom, free WiFi, bed sheets

Cabin in Townsend

Refined Modern Alpine Silos Cabin on 1,500 Acres / Private Mountain Retreat for4
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 ￥32,796
￥59,307 total
includes taxes & fees
Jan 30 - Jan 31
Refined Modern Alpine Silos Cabin on 1,500 Acres / Private Mountain Retreat for4
Property grounds

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 ￥30,508
￥60,296 total
includes taxes & fees
Jan 30 - Jan 31
Cozy cabin nestled beside a spring-fed pond&hobby farm in the Elkhorn Mountains
Fridge, microwave, oven, stovetop

Vacation Home in Helena

Cozy townhouse close to Hospital & Capital
10.0 out of 10, Exceptional, (97 reviews)
"Perfect stay!"
United States
Craig R.
The price is ￥15,788
￥31,713 total
includes taxes & fees
Feb 4 - Feb 5
Cozy townhouse close to Hospital & Capital
Interior

Cabin in Townsend

Refined Modern Alpine Silos Cabin on 1,500 Private Acres/Mountain Retreat for 4
10.0 out of 10, Exceptional, (1 review)
"Location awesome and clean cabin "
United States
Meghan J.
The price is ￥34,322
￥61,285 total
includes taxes & fees
Jan 30 - Jan 31
Refined Modern Alpine Silos Cabin on 1,500 Private Acres/Mountain Retreat for 4
Exterior

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 ￥19,068
￥34,926 total
includes taxes & fees
Jan 31 - Feb 1
Lee's apartment building on saddle mountain
Exterior

Cabin in Helena

Cabin 21 - Bicycle Retreat
10.0 out of 10, Exceptional, (1 review)
"Easy check in, good communications, good price"
United States
Jackie L.
The price is ￥9,303
￥14,001 total
includes taxes & fees
Feb 1 - Feb 2
Cabin 21 - Bicycle Retreat
Exterior

Aparthotel in Helena

Suite 32 - King Suite
9.8 out of 10, Exceptional, (16 reviews)
"Nice place to stay that avoids the hotel vibe."
United States
Erik
The price is ￥17,542
￥22,899 total
includes taxes & fees
Feb 1 - Feb 2
Suite 32 - King Suite
Outdoor dining

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 ￥20,593
￥39,538 total
includes taxes & fees
Jan 31 - Feb 1
SADDLE MOUNTAIN ESCAPE
Living area

Apartment in East Helena

Great place to crash after a Montana adventure!
8.0 out of 10, Very Good, (1 review)
"Clean quiet space. "
United States
Addy C.
The price is ￥9,152
￥13,673 total
includes taxes & fees
Feb 1 - Feb 2
Great place to crash after a Montana adventure!
Interior

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 ￥14,003
￥18,418 total
includes taxes & fees
Feb 3 - Feb 4
Trails, Tails & Town – Pet-Friendly Stay Near It All
Exterior

Vacation 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 ￥17,161
￥26,936 total
includes taxes & fees
Jan 30 - Jan 31
Helena Townhouse next to Skelton Park (Dog and kid friendly)
Terrace/patio

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 ￥13,729
￥32,125 total
includes taxes & fees
Jan 31 - Feb 1
Spacious artist's studio loft apartment with view
Property grounds

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

Vacation Home in Helena

Suite 34- Victorian Suite
7.4 out of 10, Good, (6 reviews)
"Safe, clean, had everything we needed! Conveniently located. "
United States
Melonie W.
The price is ￥17,611
￥22,989 total
includes taxes & fees
Mar 1 - Mar 2
Suite 34- Victorian Suite
2 bedrooms, WiFi, bed sheets

Vacation 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 ￥18,305
￥40,362 total
includes taxes & fees
Feb 2 - Feb 3
Giant View Home
Private kitchen

Condo in Helena

PERFECT 2 bedroom, 1 bath Condo
9.6 out of 10, Exceptional, (29 reviews)
"The place was very clean and had all the amenities needed. "
United States
Carlos O.
The price is ￥23,064
￥47,315 total
includes taxes & fees
Jan 30 - Jan 31
PERFECT 2 bedroom, 1 bath Condo
Microwave, oven, stovetop, dishwasher

Vacation Home in Helena

Charming 1-bedroom house with AC in Helena perfect for relaxing
Charming 1-bedroom house with AC in Helena perfect for relaxing
Dining

Vacation Home in Helena

Style and comfort in Helena! Easy access to any part of Helena. No cleaning fees
10.0 out of 10, Exceptional, (56 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 ￥26,771
￥33,031 total
includes taxes & fees
Feb 8 - Feb 9
Style and comfort in Helena! Easy access to any part of Helena. No cleaning fees
3 bedrooms, WiFi

Vacation Home in Helena

This cozy house has been completely remodeled inside and features three bedrooms.
10.0 out of 10, Exceptional, (3 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 ￥19,068
￥24,547 total
includes taxes & fees
Feb 1 - Feb 2
This cozy house has been completely remodeled inside and features three bedrooms.
Outdoor dining

Apartment in Helena

Apartment next to Cathedral in Historic Downtown Helena
9.0 out of 10, Wonderful, (33 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 ￥22,881
￥42,339 total
includes taxes & fees
Jan 31 - Feb 1
Apartment next to Cathedral in Historic Downtown Helena
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
"The whole process was seamless! They have excellent communication and make check-in and out a breeze. Cabins are clean, well stocked, and beds are comfy. I will always book with Lamplighter any time we are in town. "
Hannah 1-night trip
Posted 5 days 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?

Trail Lovers Getaway - walk or bike to downtown: This vacation home rental outside of Winston is located in the city center and has a garden, a selection of games, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

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.