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Winston Holiday Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Winston holiday rentals

Exterior

1. Ranch House in the Elkhorn Mountains

Ranch House in the Elkhorn Mountains
Clancy
9.8 out of 10, Exceptional, (128 reviews)
"Amazing property and hosts. Beds were amazing and house was perfect for what we needed. "
United States
Michelle E.
The price is HK$1,059
HK$1,322 total
includes taxes & fees
19 Aug - 20 Aug
Ranch House in the Elkhorn Mountains
Exterior detail

2. Rustic cabin with lake views.

Rustic cabin with lake views.
Townsend
9.6 out of 10, Exceptional, (44 reviews)
"Great location away from everything - nice view of the lake. We enjoyed the fresh air. Very clean!"
United States
Brett
The price is HK$785
HK$1,017 total
includes taxes & fees
24 Aug - 25 Aug
Rustic cabin with lake views.
Exterior

3. Lee's apartment building on saddle mountain

Lee's apartment building on saddle mountain
Clancy
10.0 out of 10, Exceptional, (68 reviews)
"Our family of four stayed here for a soccer tournament. It was so unique and the property was very nice. It fit us wonderfully and had a few pets that would come say hi every day."
United States
Chelsea F.
The price is HK$981
HK$1,788 total
includes taxes & fees
17 Aug - 18 Aug
Lee's apartment building on saddle mountain
Outdoor dining

4. 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 HK$1,059
HK$2,034 total
includes taxes & fees
17 Aug - 18 Aug
SADDLE MOUNTAIN ESCAPE
Smart TV

5. Lee's Helena Hideout

Lee's Helena Hideout
Helena
9.8 out of 10, Exceptional, (47 reviews)
"Clean and the host was great! Very nice place close to the hospital."
United States
Kara D.
The price is HK$953
HK$1,903 total
includes taxes & fees
17 Aug - 18 Aug
Lee's Helena Hideout
Coffee/tea maker, fridge, microwave, oven

6. Cozy townhouse close to Hospital & Capital

Cozy townhouse close to Hospital & Capital
Helena
10.0 out of 10, Exceptional, (110 reviews)
"Perfect stay!"
United States
Craig R.
The price is HK$847
HK$1,678 total
includes taxes & fees
25 Aug - 26 Aug
Cozy townhouse close to Hospital & Capital
Property grounds

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

Tizer Botanic Gardens Cabin 1/2 way between Yellowstone & Glacier National Parks
Jefferson City
10.0 out of 10, Exceptional, (205 reviews)
"It was a very enjoyable stay"
United States
Matthias A.
The price is HK$1,020
HK$1,271 total
includes taxes & fees
19 Aug - 20 Aug
Tizer Botanic Gardens Cabin 1/2 way between Yellowstone & Glacier National Parks
Dining

8. 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, (75 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
30 Aug - 31 Aug
Style and comfort in Helena! Easy access to any part of Helena. No cleaning fees
Exterior

9. Cozy Cabin

Cozy Cabin
Clancy
8.8 out of 10, Excellent, (42 reviews)
"Was really quiet and very enjoyable!"
United States
Kaylee N.
The price is HK$1,059
HK$1,644 total
includes taxes & fees
18 Aug - 19 Aug
Cozy Cabin
Private kitchen

10. LOVELY 2 Bedroom Fully Furnished w/ Laundry

LOVELY 2 Bedroom Fully Furnished w/ Laundry
Helena
10.0 out of 10, Exceptional, (12 reviews)
"Convenient, nice, close to town place."
United States
Jessica S.
The price is HK$1,307
HK$2,581 total
includes taxes & fees
17 Aug - 18 Aug
LOVELY 2 Bedroom Fully Furnished w/ Laundry
Exterior

11. 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, (81 reviews)
"It was a perfect weekend away from home. I would stay again. "
United States
Crystal A.
The price is HK$1,177
HK$1,746 total
includes taxes & fees
31 Aug - 1 Sept
Helena Townhouse next to Skelton Park (Dog and kid friendly)
Outdoor dining

12. 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 HK$2,461
HK$4,488 total
includes taxes & fees
31 Aug - 1 Sept
Helena Forest Hideout w/ Hot Tub Near Downtown
Interior

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

South Hills - Sleeps 12+ - Sauna, Gym, Air Hockey
Helena
The price is HK$2,415
HK$5,787 total
includes taxes & fees
25 Aug - 26 Aug
South Hills - Sleeps 12+ - Sauna, Gym, Air Hockey
Exterior

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

Suite 33 - Queen Suite W/ Walk-In Shower
Helena
9.8 out of 10, Exceptional, (7 reviews)
"This place is pretty great, and had been remodeled nicely. Perfect for a few days!"
United States
Jessica B.
The price is HK$989
HK$1,280 total
includes taxes & fees
23 Aug - 24 Aug
Suite 33 - Queen Suite W/ Walk-In Shower
Private kitchen

15. PERFECT 2 bedroom, 1 bath Condo

PERFECT 2 bedroom, 1 bath Condo
Helena
9.8 out of 10, Exceptional, (40 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.
PERFECT 2 bedroom, 1 bath Condo
Exterior

16. Suites 35 +Up - Victorian Queen

Suites 35 +Up - Victorian Queen
Helena
9.0 out of 10, Wonderful, (10 reviews)
"Exactly what we need! The perfect place to break up our trip"
United States
Sam P.
The price is HK$989
HK$1,280 total
includes taxes & fees
23 Aug - 24 Aug
Suites 35 +Up - Victorian Queen
Exterior

17. 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$989
HK$1,280 total
includes taxes & fees
17 Aug - 18 Aug
Cabin 23 - Hunters Haven
Interior

18. 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, (8 reviews)
"Great place to stay. "
United States
Mark N.
The price is HK$965
HK$1,212 total
includes taxes & fees
9 Sept - 10 Sept
Trails, Tails & Town – Pet-Friendly Stay Near It All
Outdoor dining

19. Apartment next to Cathedral in Historic Downtown Helena

Apartment next to Cathedral in Historic Downtown Helena
Helena
9.0 out of 10, Wonderful, (42 reviews)
"Very convenient location. Easy to walk everywhere downtown."
United States
Keith
The price is HK$1,059
HK$2,034 total
includes taxes & fees
1 Sept - 2 Sept
Apartment next to Cathedral in Historic Downtown Helena
Smart TV

20. Newly Remodeled Downtown Helena Home, Sleeps 11

Newly Remodeled Downtown Helena Home, Sleeps 11
Helena
9.4 out of 10, Exceptional, (15 reviews)
"Very clean and had everything we needed for the weekend! Keypad was tricky to unlock, but the host was very prompt to help us get in! Only downside was I felt like the seating wasn’t enough for the people we had! Other than that, it was a great stay."
United States
Cassidy T.
The price is HK$2,076
HK$3,726 total
includes taxes & fees
31 Aug - 1 Sept
Newly Remodeled Downtown Helena Home, Sleeps 11
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

Budget Inn Express Downtown Helena

Budget Inn Express Downtown Helena

10/10 Excellent
"Older place, very well maintained, very friendly people. Met the owner, great guy. Clean room, comfortable bed."
Shawna 1-night trip
Posted 15 hours ago
Budget Inn Express Downtown Helena

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?

Ranch House in the Elkhorn Mountains: This holiday home rental outside of Winston is located in the mountains, and has a fireplace, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as 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 wider area, you’ll find Canyon Ferry Wildlife Management Area and Montana State Capitol.

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.