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Winston Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Winston holiday 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, (46 reviews)
"The property was beautiful and perfect for 2 people. The host was very nice and communicated great with any updates needed!"
United States
peyton c.
The price is HK$785
HK$1,017 total
includes taxes & fees
16 Oct - 17 Oct
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, (132 reviews)
"The area is nice and the ranch house was good."
United States
justin p.
The price is HK$1,059
HK$1,322 total
includes taxes & fees
5 Oct - 6 Oct
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, (69 reviews)
"Clean"
United States
Terryn
The price is HK$981
HK$1,788 total
includes taxes & fees
5 Oct - 6 Oct
Lee's apartment building on saddle mountain
A house with a covered porch, stone pillars, a fire pit, and a satellite dish.

4. SADDLE MOUNTAIN ESCAPE

SADDLE MOUNTAIN ESCAPE
Clancy
10.0 out of 10, Exceptional, (44 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$1,059
HK$2,034 total
includes taxes & fees
6 Oct - 7 Oct
SADDLE MOUNTAIN ESCAPE
A wooden table with a framed poster, a glass of iced coffee, a blue vase, and three travel magazines.

5. 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, (12 reviews)
"Great place to stay. "
United States
Mark N.
The price is HK$942
HK$1,187 total
includes taxes & fees
1 Nov - 2 Nov
Trails, Tails & Town – Pet-Friendly Stay Near It All
A modern kitchen with wooden cabinets, stainless steel appliances, a granite countertop, and a central island.

6. Cozy townhouse close to Hospital & Capital

Cozy townhouse close to Hospital & Capital
Helena
10.0 out of 10, Exceptional, (117 reviews)
"Great little spacious place that was perfect for our trip"
United States
Gennie W.
The price is HK$1,052
HK$1,924 total
includes taxes & fees
25 Oct - 26 Oct
Cozy townhouse close to Hospital & Capital
A modern, dark-colored building with a flat roof and large windows.

7. 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, (21 reviews)
"Beautiful property, spotless and great location. Would definitely stay again."
United States
Christy P.
The price is HK$1,413
HK$1,737 total
includes taxes & fees
8 Oct - 9 Oct
Luxury Home with Movie Room - right outside of 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)
"Clean and the host was great! Very nice place close to the hospital."
United States
Kara D.
The price is HK$953
HK$1,894 total
includes taxes & fees
5 Oct - 6 Oct
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
9.6 out of 10, Exceptional, (8 reviews)
"This place is pretty great, and had been remodeled nicely. Perfect for a few days!"
United States
Jessica B.
The price is HK$871
HK$1,152 total
includes taxes & fees
1 Nov - 2 Nov
Suite 33 - Queen Suite W/ Walk-In Shower
A spacious kitchen with a central island, wooden flooring, pendant lighting, and a view of the outdoors.

10. 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, (82 reviews)
"This place is super clean and modern. Very nice stay!!"
United States
RON D.
The price is HK$1,377
HK$1,699 total
includes taxes & fees
11 Oct - 12 Oct
Style and comfort in Helena! Easy access to any part of Helena. No cleaning fees
A deck with a table and chairs, a white railing, and a view of a church spire.

11. 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)
"Very convenient location. Easy to walk everywhere downtown."
United States
Keith
The price is HK$953
HK$1,903 total
includes taxes & fees
11 Oct - 12 Oct
Apartment next to Cathedral in Historic Downtown Helena
A red building with a wooden staircase and a brick pathway.

12. 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.
Spacious artist's studio loft apartment with view
A two-story house with a front porch, a small front yard, and a wooden fence.

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, (90 reviews)
"It was a perfect weekend away from home. I would stay again. "
United States
Crystal A.
The price is HK$1,059
HK$1,602 total
includes taxes & fees
17 Oct - 18 Oct
Helena Townhouse next to Skelton Park (Dog and kid friendly)
A modern kitchen with dark wood cabinets, stainless steel appliances, and a central island with stools.

14. 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 HK$1,066
HK$2,279 total
includes taxes & fees
13 Oct - 14 Oct
LOVELY 2 Bedroom Fully Furnished w/ Laundry
A modern living room with a flat-screen TV displaying various streaming services, a grey sofa, a blue bean bag, and a wooden coffee table.

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

Family Retreat- Sauna, Arcade, Gym & Message Chair
Helena
10.0 out of 10, Exceptional, (2 reviews)
"Excellent stay! The home was spacious, clean, comfortable, and incredibly welcoming—it truly felt like a home away from home. The amenities were great, and everything we needed was thoughtfully provided. We felt comfortable from the moment we arrived and would absolutely stay here again. Highly recommend!"
United States
Melisa M.
The price is HK$2,649
HK$5,996 total
includes taxes & fees
13 Oct - 14 Oct
Family Retreat- Sauna, Arcade, Gym & Message Chair
A small wooden building with a garage, a wooden porch, and a window displaying a neon 'OPEN' sign.

16. 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 HK$871
HK$1,152 total
includes taxes & fees
1 Nov - 2 Nov
Cabin 23 - Hunters Haven
A modern kitchen with a central island, bar stools, wooden cabinets, stainless steel appliances, and a dining area with a table and chairs.

17. PERFECT 2 bedroom, 1 bath Condo

PERFECT 2 bedroom, 1 bath Condo
Helena
9.8 out of 10, Exceptional, (43 reviews)
"Clean and welcoming! Kitchen has everything you could ever need which was great! Neighbors were quiet, and the provided sound machines were a nice touch. Would stay here again!"
United States
Grace C.
The price is HK$1,130
HK$2,356 total
includes taxes & fees
1 Nov - 2 Nov
PERFECT 2 bedroom, 1 bath Condo
Suite #34 outside

18. Suite 34- Victorian Suite

Suite 34- Victorian Suite
Helena
7.8 out of 10, Good, (8 reviews)
"Very nice place to stay. Close to downtown and can walk to supermarket. The property was quiet and comfortable"
United States
KARL T.
The price is HK$871
HK$1,152 total
includes taxes & fees
3 Nov - 4 Nov
Suite 34- Victorian Suite
A spacious kitchen with a central island, a dining area with chairs, and a large arched doorway leading to another room.

19. 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 HK$1,692
HK$3,641 total
includes taxes & fees
11 Oct - 12 Oct
Find Your Sanctuary at The Church
A small wooden building with a garage, a wooden porch, and a window displaying a neon 'OPEN' sign.

20. 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 HK$871
HK$1,152 total
includes taxes & fees
1 Nov - 2 Nov
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

Americas Best Value Inn & Suites Helena

Americas Best Value Inn & Suites Helena

8/10 Good
"Room was adequate, Staff friendly and accommodating."
Steven 1-night trip
Posted 1 day ago
Americas Best Value Inn & Suites 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 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 spacious king bed suite, In the heart of Historic Helena, Montana!: This holiday 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 wider area, you’ll find Canyon Ferry Wildlife Management Area and Montana Historical Society Museum.

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.