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Winston Vacation Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Winston vacation rentals

A rustic wooden cabin with a bar area and several wooden chairs.

1. Ranch house in the Elkhorn Mountains

Ranch house in the Elkhorn Mountains
Clancy
9.8 out of 10, Exceptional, (135 reviews)
"The area is nice and the ranch house was good."
United States
justin p.
The price is AED 496
AED 587 total
includes taxes & fees
16 Nov - 17 Nov
Ranch house in the Elkhorn Mountains
A rustic wooden building with a sloped roof, a mounted deer skull, and a wooden fence.

2. Lee's apartment building on Saddle Mountain

Lee's apartment building on Saddle Mountain
Clancy
10.0 out of 10, Exceptional, (72 reviews)
"Very friendly and welcoming. We enjoyed every minute of our stay."
United States
Kiersten J.
The price is AED 496
AED 841 total
includes taxes & fees
16 Nov - 17 Nov
Lee's apartment building on Saddle Mountain
A modern kitchen with wooden cabinets, stainless steel appliances, a granite countertop, and a central island.

3. 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 AED 380
AED 728 total
includes taxes & fees
19 Nov - 20 Nov
Cozy townhouse close to Hospital & Capital
A deck with a table and chairs, a white railing, and a view of a church spire.

4. Apartment next to Cathedral in Historic Downtown Helena

Apartment next to Cathedral in Historic Downtown Helena
Helena
9.2 out of 10, Wonderful, (48 reviews)
"Great property and location. If you have kids, air hockey table is a big hit."
United States
Chris D.
The price is AED 446
AED 847 total
includes taxes & fees
16 Nov - 17 Nov
Apartment next to Cathedral in Historic Downtown Helena
A covered patio with stone pillars, a fire pit, and a view of a forested area.

5. SADDLE MOUNTAIN ESCAPE

SADDLE MOUNTAIN ESCAPE
Clancy
10.0 out of 10, Exceptional, (47 reviews)
"We only stayed one night, but I really wish we could’ve stayed more. It was so comfortable and relaxing. All the amenities were provided.And the owners are conscientious and kind. Can’t wait to plan my next trip there with my daughters for a girls weekend"
United States
Paula T.
The price is AED 533
AED 924 total
includes taxes & fees
16 Nov - 17 Nov
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)
"Great location with beautiful views."
United States
Brodie N.
The price is AED 579
AED 680 total
includes taxes & fees
16 Nov - 17 Nov
Luxury Home with Movie Room - right outside of Helena
A spacious kitchen with a central island, wooden flooring, pendant lighting, and a view of the outdoors.

7. 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, (88 reviews)
"Very nice house with everything we could have need. The TV-seats are very comfortable Would come again "
United States
Denise H.
The price is AED 645
AED 724 total
includes taxes & fees
22 Nov - 23 Nov
Style and comfort in Helena! Easy access to any part of Helena. No cleaning fees
A two-story house with a front porch, a small front yard, and a wooden fence.

8. 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, (100 reviews)
"Great location and had everything we needed."
United States
Kristine
The price is AED 496
AED 714 total
includes taxes & fees
19 Nov - 20 Nov
Helena Townhouse next to Skelton Park (Dog and kid friendly)
A dog sitting outside a house with a red door and a window. There are two chairs, one blue and one green, and a stone wall in the background.

9. 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, (16 reviews)
"Great place to stay. "
United States
Mark N.
The price is AED 477
AED 563 total
includes taxes & fees
16 Nov - 17 Nov
Trails, Tails & Town – Pet-Friendly Stay Near It All
A residential building with a front door, a welcome sign, and a utility box.

10. LOVELY 2 Bedroom Fully Furnished w/ Laundry

LOVELY 2 Bedroom Fully Furnished w/ Laundry
Helena
9.8 out of 10, Exceptional, (19 reviews)
"Great stay! I would stay again. Great location to utilize the hot springs!!"
United States
Alisha H.
The price is AED 498
AED 986 total
includes taxes & fees
21 Nov - 22 Nov
LOVELY 2 Bedroom Fully Furnished w/ Laundry
A concrete pathway flanked by a wooden fence on one side and a stone wall on the other, leading up a set of steps.

11. 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 AED 1,306
AED 2,779 total
includes taxes & fees
16 Nov - 17 Nov
Family Retreat- Sauna, Arcade, Gym & Message Chair
A modern kitchen with a large island, bar stools, stainless steel appliances, and wooden cabinets.

12. 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 AED 498
AED 1,017 total
includes taxes & fees
16 Nov - 17 Nov
PERFECT 2 bedroom, 1 bath Condo
A house with a garage, a small deck, and a lawn with trees.

13. 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 AED 833
AED 1,625 total
includes taxes & fees
16 Nov - 17 Nov
Helena Forest Hideout w/ Hot Tub Near Downtown
A red building with a wooden staircase and a brick pathway.

14. 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 AED 415
AED 920 total
includes taxes & fees
16 Nov - 17 Nov
Spacious artist's studio loft apartment with view
A red brick church with a green steeple, surrounded by trees and hills.

15. 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 AED 792
AED 1,621 total
includes taxes & fees
19 Nov - 20 Nov
Find Your Sanctuary at The Church
Overhead view of the property

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 AED 279
AED 554 total
includes taxes & fees
16 Nov - 17 Nov
Cabin 23 - Hunters Haven
A snow-covered residential area with a sign for 'LAMPLIGHTER CABINS & SUITES'.

17. 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.
The price is AED 279
AED 526 total
includes taxes & fees
22 Nov - 23 Nov
Suite 33 - Queen Suite W/ Walk-In Shower
A snow-covered residential area with a sign for 'LAMPLIGHTER CABINS & SUITES'.

18. Suites 35 +Up - Victorian Queen

Suites 35 +Up - Victorian Queen
Helena
9.4 out of 10, Exceptional, (13 reviews)
"Perfect stop!"
United States
Kathy M.
The price is AED 279
AED 654 total
includes taxes & fees
16 Nov - 17 Nov
Suites 35 +Up - Victorian Queen
A modern A-frame house with a hot tub and outdoor seating area.

19. Secluded Montana A-Frame with Hot Tub and Views

Secluded Montana A-Frame with Hot Tub and Views
Jefferson City
10.0 out of 10, Exceptional, (31 reviews)
"We had a wonderful and relaxing time. This place is extremely clean and comfortable, very private and beautiful sceneries. "
United States
Anonymous traveler
The price is AED 2,002
AED 2,995 total
includes taxes & fees
26 Nov - 27 Nov
Secluded Montana A-Frame with Hot Tub and Views
A room with a wooden bookshelf containing books and decorative items, a white door, and a standing mirror.

20. Newly Remodeled Downtown Helena Home, Sleeps 11

Newly Remodeled Downtown Helena Home, Sleeps 11
Helena
9.4 out of 10, Exceptional, (16 reviews)
"Great stay! Second time booking here! Highly recommend!"
United States
Radhika W.
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

La Quinta Inn & Suites by Wyndham Helena

La Quinta Inn & Suites by Wyndham Helena

8/10 Good
"nothing"
Matt 3-night trip
Posted 6 hours ago
La Quinta Inn & Suites by Wyndham Helena

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.