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Winston Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Winston vacation rentals

A wooden cabin with a green roof, a front door, and two windows.

1. Rustic cabin with lake views.

Rustic cabin with lake views.
Townsend
9.6 out of 10, Exceptional, (47 reviews)
"Quiet"
United States
Matthew
Rustic cabin with lake views.
Two rustic cabins with metal roofs, surrounded by a grassy field and trees.

2. Ranch House in the Elkhorn Mountains

Ranch House in the Elkhorn Mountains
Clancy
9.8 out of 10, Exceptional, (133 reviews)
"The area is nice and the ranch house was good."
United States
justin p.
The price is ￥21,271
￥25,185 total
includes taxes & fees
Nov 11 - Nov 12
Ranch House in the Elkhorn Mountains
A rustic wooden building with a sloped roof, a mounted deer skull, and a wooden fence.

3. Lee's apartment building on saddle mountain

Lee's apartment building on saddle mountain
Clancy
10.0 out of 10, Exceptional, (71 reviews)
"Very friendly and welcoming. We enjoyed every minute of our stay."
United States
Kiersten J.
The price is ￥21,271
￥36,075 total
includes taxes & fees
Nov 5 - Nov 6
Lee's apartment building on saddle mountain
A modern kitchen with wooden cabinets, stainless steel appliances, a granite countertop, and a central island.

4. Cozy townhouse close to Hospital & Capital

Cozy townhouse close to Hospital & Capital
Helena
10.0 out of 10, Exceptional, (119 reviews)
"Great little spacious place that was perfect for our trip"
United States
Gennie W.
The price is ￥16,318
￥32,778 total
includes taxes & fees
Nov 1 - Nov 2
Cozy townhouse close to Hospital & Capital
A house with a covered porch, stone pillars, a fire pit, and a satellite dish.

5. SADDLE MOUNTAIN ESCAPE

SADDLE MOUNTAIN ESCAPE
Clancy
10.0 out of 10, Exceptional, (47 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 ￥22,846
￥38,797 total
includes taxes & fees
Nov 1 - Nov 2
SADDLE MOUNTAIN ESCAPE
A modern, dark-colored building with a flat roof and large windows.

6. 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, (22 reviews)
"Beautiful property, spotless and great location. Would definitely stay again."
United States
Christy P.
The price is ￥31,512
￥35,224 total
includes taxes & fees
Nov 30 - Dec 1
Luxury Home with Movie Room - right outside of Helena
A deck with a table and chairs, a white railing, and a view of a church spire.

7. Apartment next to Cathedral in Historic Downtown Helena

Apartment next to Cathedral in Historic Downtown Helena
Helena
9.2 out of 10, Wonderful, (46 reviews)
"A clean, charming, comfy place to stay next door the the beautiful Cathedral of St. Helena. It was a perfect fit for our family!"
United States
Sara M.
The price is ￥19,144
￥36,331 total
includes taxes & fees
Nov 17 - Nov 18
Apartment next to Cathedral in Historic Downtown Helena
A hallway with a wooden floor, a gray wall with a 'HOME SWEET HOME' sign, a gray chair, and a TV.

8. Lee's Helena Hideout

Lee's Helena Hideout
Helena
9.8 out of 10, Exceptional, (48 reviews)
"This is a great place to stay that’s close to most everything in Helena. It had everything our family of four needed and Debbie is great to communicate with. Highly recommended!!"
United States
Amy C.
The price is ￥20,575
￥39,929 total
includes taxes & fees
Nov 12 - Nov 13
Lee's Helena Hideout
A small wooden building with a garage, a wooden porch, and a window displaying a neon 'OPEN' sign.

9. Suite 33 - Queen Suite W/ Walk-In Shower

Suite 33 - Queen Suite W/ Walk-In Shower
Helena
9.4 out of 10, Exceptional, (9 reviews)
"This place is pretty great, and had been remodeled nicely. Perfect for a few days!"
United States
Jessica B.
Suite 33 - Queen Suite W/ Walk-In Shower
A modern kitchen with dark wood cabinets, stainless steel appliances, and a central island with stools.

10. LOVELY 2 Bedroom Fully Furnished w/ Laundry

LOVELY 2 Bedroom Fully Furnished w/ Laundry
Helena
9.8 out of 10, Exceptional, (18 reviews)
"Great stay! I would stay again. Great location to utilize the hot springs!!"
United States
Alisha H.
The price is ￥20,420
￥42,472 total
includes taxes & fees
Nov 2 - Nov 3
LOVELY 2 Bedroom Fully Furnished w/ Laundry
A red building with a wooden staircase and a brick pathway.

11. 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)
"Wonderful place to stay!"
United States
Raquel W.
The price is ￥17,016
￥38,457 total
includes taxes & fees
Nov 1 - Nov 2
Spacious artist's studio loft apartment with view
A two-story house with a front porch, a small front yard, and a wooden fence.

12. 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, (98 reviews)
"Nice cozy location in Helena, with convenient access to nearby points of interest."
United States
Richard K.
The price is ￥21,271
￥30,630 total
includes taxes & fees
Nov 7 - Nov 8
Helena Townhouse next to Skelton Park (Dog and kid friendly)
A modern kitchen with a central island, bar stools, wooden cabinets, stainless steel appliances, and a dining area with a table and chairs.

13. PERFECT 2 bedroom, 1 bath Condo

PERFECT 2 bedroom, 1 bath Condo
Helena
9.8 out of 10, Exceptional, (44 reviews)
"Great place."
United States
Russ B.
The price is ￥20,433
￥42,499 total
includes taxes & fees
Nov 8 - Nov 9
PERFECT 2 bedroom, 1 bath Condo
A small wooden building with a garage, a wooden porch, and a window displaying a neon 'OPEN' sign.

14. Cabin 23 - Hunters Haven

Cabin 23 - Hunters Haven
Helena
9.4 out of 10, Exceptional, (3 reviews)
"It was a great stay. The cabin is a little small, next time we will get a booger cabin. We lived our stay"
United States
Valerie L.
The price is ￥10,397
￥22,066 total
includes taxes & fees
Dec 1 - Dec 2
Cabin 23 - Hunters Haven
A wooden table with a framed poster, a glass of iced coffee, a blue vase, and three travel magazines.

15. 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, (15 reviews)
"Great place to stay. "
United States
Mark N.
The price is ￥20,483
￥24,164 total
includes taxes & fees
Nov 10 - Nov 11
Trails, Tails & Town – Pet-Friendly Stay Near It All
A small wooden building with a garage, a wooden porch, and a window displaying a neon 'OPEN' sign.

16. Suites 35 +Up - Victorian Queen

Suites 35 +Up - Victorian Queen
Helena
9.4 out of 10, Exceptional, (13 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 ￥10,397
￥26,175 total
includes taxes & fees
Nov 3 - Nov 4
Suites 35 +Up - Victorian Queen
A small wooden building with a garage, a wooden porch, and a window displaying a neon 'OPEN' sign.

17. Cabin 26 - Coyboy Corner

Cabin 26 - Coyboy Corner
Helena
9.0 out of 10, Wonderful, (2 reviews)
"Great place, very clean and it was perfect for our one-night stay in Helena. We would stay there again"
United States
Ana Z.
The price is ￥10,404
￥20,888 total
includes taxes & fees
Nov 1 - Nov 2
Cabin 26 - Coyboy Corner
A spacious kitchen with a central island, a dining area with chairs, and a large arched doorway leading to another room.

18. Find Your Sanctuary at The Church

Find Your Sanctuary at The Church
Helena
10.0 out of 10, Exceptional, (15 reviews)
"Great stay"
United States
David Y.
The price is ￥33,970
￥69,530 total
includes taxes & fees
Nov 5 - Nov 6
Find Your Sanctuary at The Church
A massage chair by BOSSCARE in a room with a large window, a potted plant, a candle, and a mug.

19. Family Retreat- Sauna, Arcade, Gym & Message Chair

Family Retreat- Sauna, Arcade, Gym & Message Chair
Helena
10.0 out of 10, Exceptional, (3 reviews)
"The house was amazing! Our family enjoyed the kid friendly setup and all the fun things the house had to offer. We will definitely stay again when we return in the future."
United States
Justin D.
The price is ￥54,358
￥121,838 total
includes taxes & fees
Nov 17 - Nov 18
Family Retreat- Sauna, Arcade, Gym & Message Chair
A rustic cabin with a patio area featuring outdoor furniture and a grill.

20. Helena Forest Hideout w/ Hot Tub Near Downtown

Helena Forest Hideout w/ Hot Tub Near Downtown
Helena
9.6 out of 10, Exceptional, (17 reviews)
"Beautiful location, scenery"
United States
Rhonda H.
The price is ￥35,719
￥69,717 total
includes taxes & fees
Nov 2 - Nov 3
Helena Forest Hideout w/ Hot Tub Near Downtown
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

Baymont by Wyndham Helena

Baymont by Wyndham Helena

10/10 Excellent
"The bathroom needs updating...Breakfast was great."
Michelle 2-night trip
Posted 8 hours ago
Baymont by Wyndham Helena

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:

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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.