Winston Vacation Rentals

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Vacation Rentals in Winston

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

10.0 out of 10, Exceptional, (185)
"We had a great time. "
$150 nightly
The price is $162
Sep 1 - Sep 2
Total with taxes and fees
Tizer Botanic Gardens Cabin 1/2 way between Yellowstone & Glacier National Parks

The west shore getaway on Canyon Ferry.

9.8 out of 10, Exceptional, (44)
"What an amazing stay. The property is perhaps the most beautiful on the lake. Great fishing. Everything was there that we needed or forgot to bring. Exceptionally clean and well maintained. Games and beautiful areas on the porch or inside for family time. Walking distance from schooners restaurant and the marina. Will book more stays with this wonderful host. "
The west shore getaway on Canyon Ferry.

Helena Townhouse next to Skelton Park (Dog and kid friendly)

9.8 out of 10, Exceptional, (41)
"Fantastic place, wish we could have stayed longer. Just what we needed and just as advertised "
$206 nightly
The price is $222
Sep 21 - Sep 22
Total with taxes and fees
Helena Townhouse next to Skelton Park (Dog and kid friendly)

Townhouse in beautiful North Helena Valley, below the majestic Sleeping Giant

2.0 star property
10.0 out of 10, Exceptional, (23)
"5 nights, rental was superb in every way. Large, clean, great location. Will be back!"
Townhouse in beautiful North Helena Valley, below the majestic Sleeping Giant

Lee's Helena Hideout

10.0 out of 10, Exceptional, (36)
"We stayed on our way to Yellowstone and it was wonderful. We were able to easily get our groceries for our adventure and have a wonderful meal at the condo. It was a perfect rest before a great vacation. "
$225 nightly
The price is $242
Sep 2 - Sep 3
Total with taxes and fees
Lee's Helena Hideout

Cozy townhouse close to Hospital & Capital

10.0 out of 10, Exceptional, (84)
"Great place! Would stay again. "
$176 nightly
The price is $190
Sep 1 - Sep 2
Total with taxes and fees
Cozy townhouse close to Hospital & Capital

Mountain Hideaway Retreat- Room for Everyone

2.0 star property
10.0 out of 10, Exceptional, (15)
"We had an amazing weekend. The house was gorgeous and so clean. There was room for everyone and comfortable for adults and the kiddos. The air hockey table was an absolute hit. "
Mountain Hideaway Retreat- Room for Everyone

Ranch House in the Elkhorn Mountains

10.0 out of 10, Exceptional, (114)
"It is a very charming and unique house."
$146 nightly
The price is $158
Sep 8 - Sep 9
Total with taxes and fees
Ranch House in the Elkhorn Mountains

Rustic cabin with lake views.

9.6 out of 10, Exceptional, (36)
"The host Beth was very helpful!"
$120 nightly
The price is $130
Sep 9 - Sep 10
Total with taxes and fees
Rustic cabin with lake views.

Cozy spacious king bed suite, In the heart of Historic Helena, Montana!

9.8 out of 10, Exceptional, (144)
"Great place to stay. Would stay there again."
Cozy spacious king bed suite, In the heart of Historic Helena, Montana!

The Nest on Main - Walking distance to downtown Helena!

10.0 out of 10, Exceptional, (98)
"Great location, adorable house. "
The Nest on Main - Walking distance to downtown Helena!

Mountain Retreat close to town.

9.8 out of 10, Exceptional, (16)
"Clean, well equipped, comfy beds, serene surroundings, close to town, Whitney is the best!"
Mountain Retreat close to town.

You and Fido welcome here!

9.6 out of 10, Exceptional, (21)
"Enjoyed our visit very much. Welcoming, clean and perfect for our fur boy. "
You and Fido welcome here!

Spacious lakefront home with stunning views!

10.0 out of 10, Exceptional, (1)
"Amazing stay with great warm and friendly hosts lots of room and a view that will take your breath away. So many fun activities to engage in. "
Spacious lakefront home with stunning views!

Cabin 24 - Helena Hideaway

8.6 out of 10, Excellent, (7)
"Very quiet, nice place. "
$140 nightly
The price is $151
Sep 1 - Sep 2
Total with taxes and fees
Cabin 24 - Helena Hideaway

Hauser Lake Waterfront-Direct access and amazing VIEWS

9.8 out of 10, Exceptional, (25)
"Great house on a beautiful lake. We loved our stay and Amy was helpful with everything."
Hauser Lake Waterfront-Direct access and amazing VIEWS

Updated Helena Condo - Walk to Downtown Spots

10.0 out of 10, Exceptional, (35)
"It was a great spot to stay. Very clean!!"
Updated Helena Condo - Walk to Downtown Spots

Cozy Cabin

9.0 out of 10, Wonderful, (31)
"It was misrepresented and as a result I never stayed there"
$195 nightly
The price is $211
Aug 31 - Sep 1
Total with taxes and fees
Cozy Cabin

Lake Helena Lookout: Gourmet Kitchen, Gorgeous Views, Unforgettable Stay

10.0 out of 10, Exceptional, (3)
"Great stay!"
Lake Helena Lookout: Gourmet Kitchen, Gorgeous Views, Unforgettable Stay

Lake Front Lodge: Your ideal Montana getaway! Watercraft rental available!

10.0 out of 10, Exceptional, (8)
"This property is absolutely beautiful with stunning lake front location and stunning views. Great layout and amenities. Amy has been incredibly helpful and quick to respond with any questions I have. We thoroughly enjoyed our time here and will most likely rent here again."
Lake Front Lodge: Your ideal Montana getaway! Watercraft rental available!
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

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 $130 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 Hauser Dam.

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.