Winston Vacation Rentals

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Our top choices for Winston vacation rentals

Cabin in Townsend

Mountain Silo #7
10.0 out of 10, Exceptional, (5)
"What a wonderful stay at the Mountain Silo. A beautifully and thoughtfully decorated and appointed unit. Not a detail was overlooked. Would definitely stay again. Tina is a wonderful host. The property is magical!"
United States
sue l.
$361 nightly
The price is $390
Dec 14 - Dec 15
Total with taxes and fees
Mountain Silo #7
10.0 out of 10, Exceptional, (94)
"We really enjoyed our time the home was very cozy and in the perfect location "
United States
Ashley B.
$193 nightly
The price is $208
Dec 13 - Dec 14
Total with taxes and fees
Cozy townhouse close to Hospital & Capital
10.0 out of 10, Exceptional, (21)
"Very cute cabin and property. Enjoyed our time."
United States
Amanda F.
$367 nightly
The price is $396
Dec 14 - Dec 15
Total with taxes and fees
Cozy cabin nestled beside a spring-fed pond&hobby farm in the Elkhorn Mountains
$310 nightly
The price is $335
Dec 13 - Dec 14
Total with taxes and fees
Montana's Tranquil Dry Creek Hideaway
$140 nightly
The price is $151
Dec 15 - Dec 16
Total with taxes and fees
Adorable 2-bedroom cottage in wonderful Helena for a quiet and relaxing stay.
10.0 out of 10, Exceptional, (117)
"Lovely place! We enjoyed our stay. "
United States
Alisa T.
$146 nightly
The price is $158
Dec 14 - Dec 15
Total with taxes and fees
Ranch House in the Elkhorn Mountains

Aparthotel in Helena

Suite 28 - Double Queen Suite
10.0 out of 10, Exceptional, (1)
"The double queen suite was perfect for a couple of dudes coming to fish Montana. Clean, Cool and Comfortable. Great location too. Quick access to downtown restaurants and to highway for travel. Will likely book again."
United States
Rob G.
$114 nightly
The price is $123
Dec 15 - Dec 16
Total with taxes and fees
Suite 28 - Double Queen Suite

Cabin in Townsend

Mountain Sio #6
10.0 out of 10, Exceptional, (1)
"Location awesome and clean cabin "
United States
Meghan J.
$372 nightly
The price is $402
Dec 14 - Dec 15
Total with taxes and fees
Mountain Sio #6
10.0 out of 10, Exceptional, (64)
"The place was great. We were also greeted by a couple of sweet dogs and a kitty cat! It would be a great place any time of year, but I bet winter time would be fun with the atmosphere of the place. "
United States
Katharine H.
$212 nightly
The price is $229
Dec 13 - Dec 14
Total with taxes and fees
Lee's apartment building on saddle mountain
9.8 out of 10, Exceptional, (8)
"We enjoyed this "
United States
Mary L.
$195 nightly
The price is $211
Dec 19 - Dec 20
Total with taxes and fees
Spacious artist's studio loft apartment with view
9.0 out of 10, Wonderful, (2)
"Cute and clean cabins in Helena - the Movie Cabin is a nod to Myrna Loy and Gary Cooper, which are fun touches. Cabin 22 is very compact and clean. The mini fridge was a plus. "
United States
Angela H.
$94 nightly
The price is $102
Dec 14 - Dec 15
Total with taxes and fees
Cabin 22 - The Movie Cabin
10.0 out of 10, Exceptional, (53)
"Beautiful property! Close to coffee shops and restaurants. Super comfortable! We definitely enjoyed our stay and would recommend it to everyone!"
United States
N N.
$149 nightly
The price is $161
Jan 3 - Jan 4, 2026
Total with taxes and fees
Helena Townhouse next to Skelton Park (Dog and kid friendly)

Vacation Home in Helena

Suites 35 +Up - Victorian Queen
9.4 out of 10, Exceptional, (9)
"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.
$124 nightly
The price is $134
Dec 15 - Dec 16
Total with taxes and fees
Suites 35 +Up - Victorian Queen
10.0 out of 10, Exceptional, (2)
"The house was perfect for my family. Dogs had a fenced yard and the facilities were close to the college and golf course. "
United States
Scott O.
$149 nightly
The price is $161
Dec 14 - Dec 15
Total with taxes and fees
This cozy house has been completely remodeled inside and features three bedrooms.

Apartment in Clancy

SADDLE MOUNTAIN ESCAPE
9.8 out of 10, Exceptional, (40)
"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.
$239 nightly
The price is $258
Dec 31 - Jan 1, 2026
Total with taxes and fees
SADDLE MOUNTAIN ESCAPE
2.0 star property
$75 nightly
The price is $81
Dec 17 - Dec 18
Total with taxes and fees
Great place to crash after a Montana adventure!

Vacation Home in Helena

Giant View Home
10.0 out of 10, Exceptional, (14)
"Great views. Perfect location for working and playing in/around Helena. I will book this place the next time we get to go to Montana."
United States
John T.
$236 nightly
The price is $255
Dec 14 - Dec 15
Total with taxes and fees
Giant View Home
10.0 out of 10, Exceptional, (192)
"Super cute cabin and the host was extremely friendly and easy to work with. "
United States
Joel H.
$150 nightly
The price is $162
Dec 31 - Jan 1, 2026
Total with taxes and fees
Tizer Botanic Gardens Cabin 1/2 way between Yellowstone & Glacier National Parks

Condo in Helena

Lee's Helena Hideout
9.8 out of 10, Exceptional, (39)
"Had a great stay with all the comforts of home!"
United States
amy m.
$239 nightly
The price is $258
Dec 31 - Jan 1, 2026
Total with taxes and fees
Lee's Helena Hideout
10.0 out of 10, Exceptional, (54)
"Cozy and very clean. I would stay here again anytime!"
United States
Joelle H.
$201 nightly
The price is $217
Dec 14 - Dec 15
Total with taxes and fees
Style and comfort in Helena! Easy access to any part of Helena. No cleaning fees
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

Find out more about Winston

Everything you need to know about Winston vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winston vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winston vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winston vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winston. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winston in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $123 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winston rentals

At Expedia, we put the best Winston vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winston rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winston vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winston. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Helena Townhouse next to Skelton Park (Dog and kid friendly): This vacation home rental outside of Winston is located near skiing and has a fireplace, a garden, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. 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 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.