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Winston Vacation 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 vacation 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 AED 496
AED 619 total
includes taxes & fees
14 Aug - 15 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 AED 367
AED 476 total
includes taxes & fees
20 Aug - 21 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 AED 459
AED 841 total
includes taxes & fees
6 Sep - 7 Sep
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 AED 496
AED 952 total
includes taxes & fees
10 Sep - 11 Sep
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 AED 446
AED 891 total
includes taxes & fees
14 Aug - 15 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 AED 450
AED 851 total
includes taxes & fees
22 Aug - 23 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 AED 477
AED 595 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)
"Perfect fit for our family trip to Helena! "
United States
Katie W.
The price is AED 694
AED 857 total
includes taxes & fees
17 Aug - 18 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, (41 reviews)
"Was really quiet and very enjoyable!"
United States
Kaylee N.
The price is AED 551
AED 841 total
includes taxes & fees
5 Sep - 6 Sep
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 AED 602
AED 1,197 total
includes taxes & fees
16 Aug - 17 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 AED 551
AED 817 total
includes taxes & fees
31 Aug - 1 Sep
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.
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
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 AED 463
AED 599 total
includes taxes & fees
10 Sep - 11 Sep
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.
The price is AED 529
AED 1,107 total
includes taxes & fees
31 Aug - 1 Sep
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.
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 AED 463
AED 599 total
includes taxes & fees
16 Aug - 17 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.
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 AED 496
AED 952 total
includes taxes & fees
1 Sep - 2 Sep
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)
"We loved our stay here! "
United States
Jennifer B.
The price is AED 998
AED 1,776 total
includes taxes & fees
31 Aug - 1 Sep
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

Best Western Helena/Capitol Hotel

Best Western Helena/Capitol Hotel

8/10 Good
"Staff were very helpful. Room was decent and clean. That said, the hotel is in need of an overall upgrade. The lady overseeing the morning breakfast was extremely nice, but the layout of the breakfast was very odd (they may be remodeling the breakfast area)."
Kimberly 3-night trip
Posted 16 hours ago
Best Western Helena/Capitol Hotel

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?

Ranch House in the Elkhorn Mountains: This vacation home rental outside of Winston is located in the mountains and has a fireplace, a garden, and a barbecue grill 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 vacation with amenities like 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 larger area, you’ll find Canyon Ferry Wildlife Management Area and Montana State Capitol.

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.