Winston Vacation Rentals

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Our top choices for Winston vacation rentals

Refined Modern Alpine Silos Cabin on 1,500 Acres / Private Mountain Retreat for4

Refined Modern Alpine Silos Cabin on 1,500 Acres / Private Mountain Retreat for4
Townsend
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful property and a true escape into the heart of Montana. What a wonderful place for us to celebrate our 30th anniversary. Thank you!!!!"
United States
Sheila E.
$361 nightly
The price is $390
Mar 3 - Mar 4
Total with taxes and fees
Refined Modern Alpine Silos Cabin on 1,500 Acres / Private Mountain Retreat for4

Refined Modern Alpine Silos Cabin on 1,500 Private Acres/Mountain Retreat for 4

Refined Modern Alpine Silos Cabin on 1,500 Private Acres/Mountain Retreat for 4
Townsend
10.0 out of 10, Exceptional, (1 review)
"Location awesome and clean cabin "
United States
Meghan J.
$372 nightly
The price is $402
Mar 3 - Mar 4
Total with taxes and fees
Refined Modern Alpine Silos Cabin on 1,500 Private Acres/Mountain Retreat for 4

Great place to crash after a Montana adventure!

Great place to crash after a Montana adventure!
East Helena
9.0 out of 10, Wonderful, (2 reviews)
"Clean quiet space. "
United States
Addy C.
$91 nightly
The price is $98
Mar 3 - Mar 4
Total with taxes and fees
Great place to crash after a Montana adventure!

Cozy townhouse close to Hospital & Capital

Cozy townhouse close to Hospital & Capital
Helena
10.0 out of 10, Exceptional, (99 reviews)
"Perfect stay!"
United States
Craig R.
$193 nightly
The price is $208
Mar 3 - Mar 4
Total with taxes and fees
Cozy townhouse close to Hospital & Capital

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.
$101 nightly
The price is $109
Mar 5 - Mar 6
Total with taxes and fees
Suite 33 - Queen Suite W/ Walk-In Shower

Lee's apartment building on saddle mountain

Lee's apartment building on saddle mountain
Clancy
10.0 out of 10, Exceptional, (64 reviews)
"So much thoughtful care was put into creating this bunkhouse retreat. We especially loved the friendly dogs that greeted us in the morning."
United States
Audrey H.
$212 nightly
The price is $229
Mar 3 - Mar 4
Total with taxes and fees
Lee's apartment building on saddle mountain

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, (63 reviews)
"Nice property, great price, great location "
United States
Joan J.
$139 nightly
The price is $150
Mar 13 - Mar 14
Total with taxes and fees
Helena Townhouse next to Skelton Park (Dog and kid friendly)

Cabin 23 - Hunters Haven

Cabin 23 - Hunters Haven
Helena
8.0 out of 10, Very Good, (1 review)
"Not fancy, but comfortable, which fits me perfectly. Heater worked well, comfy bed, cute decor. Easy access."
United States
Christopher
$101 nightly
The price is $109
Mar 3 - Mar 4
Total with taxes and fees
Cabin 23 - Hunters Haven

Apartment next to Cathedral in Historic Downtown Helena

Apartment next to Cathedral in Historic Downtown Helena
Helena
9.0 out of 10, Wonderful, (33 reviews)
"Great place to stay that is right next to downtown! It was very clean when we arrived! Overall, great place to stay!"
United States
Braden P.
$217 nightly
The price is $234
Mar 3 - Mar 4
Total with taxes and fees
Apartment next to Cathedral in Historic Downtown Helena

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, (58 reviews)
"We enjoyed our stay. It was clean, cozy, well-appointed and had everything we needed. I would certainly stay there again. "
United States
Laura A.
$216 nightly
The price is $233
Mar 3 - Mar 4
Total with taxes and fees
Style and comfort in Helena! Easy access to any part of Helena. No cleaning fees

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, (3 reviews)
"Awesome great place!"
United States
Valarie S.
$129 nightly
The price is $139
Apr 1 - Apr 2
Total with taxes and fees
Trails, Tails & Town – Pet-Friendly Stay Near It All

PERFECT 2 bedroom, 1 bath Condo

PERFECT 2 bedroom, 1 bath Condo
Helena
9.6 out of 10, Exceptional, (30 reviews)
"The place was very clean and had all the amenities needed. "
United States
Carlos O.
$287 nightly
The price is $310
Mar 3 - Mar 4
Total with taxes and fees
PERFECT 2 bedroom, 1 bath Condo

Giant View Home

Giant View Home
Helena
10.0 out of 10, Exceptional, (18 reviews)
"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.
$280 nightly
The price is $302
Mar 3 - Mar 4
Total with taxes and fees
Giant View Home

Spacious artist's studio loft apartment with view

Spacious artist's studio loft apartment with view
Helena
9.8 out of 10, Exceptional, (8 reviews)
"We enjoyed this "
United States
Mary L.
$217 nightly
The price is $234
Mar 13 - Mar 14
Total with taxes and fees
Spacious artist's studio loft apartment with view

Suite 35 - Victorian Suite W/ Porch

Suite 35 - Victorian Suite W/ Porch
Helena
8.0 out of 10, Very Good, (2 reviews)
"Stayed here twice after picking up each of our 2 boxer puppies in Bozeman on our way back to Kalispell. Wonderful area with beautiful historic houses."
United States
Andrea R.
$111 nightly
The price is $120
Mar 8 - Mar 9
Total with taxes and fees
Suite 35 - Victorian Suite W/ Porch

This cozy house has been completely remodeled inside and features three bedrooms.

This cozy house has been completely remodeled inside and features three bedrooms.
Helena
10.0 out of 10, Exceptional, (3 reviews)
"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.
$150 nightly
The price is $162
Mar 5 - Mar 6
Total with taxes and fees
This cozy house has been completely remodeled inside and features three bedrooms.

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.
$125 nightly
The price is $135
Mar 15 - Mar 16
Total with taxes and fees
Cabin 26 - Coyboy Corner

Cabin 22 - The Movie Cabin

Cabin 22 - The Movie Cabin
Helena
8.8 out of 10, Excellent, (3 reviews)
"Nice affordable place"
United States
Jackie L.
$101 nightly
The price is $109
Mar 11 - Mar 12
Total with taxes and fees
Cabin 22 - The Movie Cabin

Suite 32 - King Suite

Suite 32 - King Suite
Helena
9.8 out of 10, Exceptional, (16 reviews)
"Nice place to stay that avoids the hotel vibe."
United States
Erik
$111 nightly
The price is $120
Mar 3 - Mar 4
Total with taxes and fees
Suite 32 - King Suite

Cabin 25 - The Ski Lodge

Cabin 25 - The Ski Lodge
Helena
8.8 out of 10, Excellent, (6 reviews)
"Location and friendliness"
United States
Isidor R.
$111 nightly
The price is $120
Mar 8 - Mar 9
Total with taxes and fees
Cabin 25 - The Ski Lodge
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 $135 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?

Cozy townhouse close to Hospital & Capital: This vacation home rental outside of Winston offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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.