Winston Vacation Rentals

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Vacation Rentals in Winston

Vacation Home in Helena

10.0 out of 10, Exceptional, (53)
"Clean, comfortable, convenient. Thanks!"
United States
caleb
$139 nightly
The price is $150
Dec 7 - Dec 8
Total with taxes and fees
Helena Townhouse next to Skelton Park (Dog and kid friendly)

Vacation Home in Helena

10.0 out of 10, Exceptional, (106)
"The place was very nice and cozy just as listed. Lots to see in town. "
United States
Natalie K.
The Nest on Main - Walking distance to downtown Helena!

Cabin in Helena

9.8 out of 10, Exceptional, (46)
"Great place! Beautiful views of the lake and plenty of room for our family! Fun times!"
United States
Cindy M.
The west shore getaway on Canyon Ferry.

Vacation Home in Helena

10.0 out of 10, Exceptional, (126)
"we had a great time, great place to stay. we will definitely be back!"
United States
Jones B.
The Wheelhouse on Main

Vacation Home in Helena

10.0 out of 10, Exceptional, (93)
"We really enjoyed our time the home was very cozy and in the perfect location "
United States
Ashley B.
$176 nightly
The price is $190
Nov 29 - Nov 30
Total with taxes and fees
Cozy townhouse close to Hospital & Capital

Vacation Home in Helena

2.0 star property
10.0 out of 10, Exceptional, (29)
"Very clean! Very well stocked with basic needs and extras. Just an awesome place for the price we paid. "
United States
Tate
Townhouse in beautiful North Helena Valley, below the majestic Sleeping Giant

Vacation Home in Helena

10.0 out of 10, Exceptional, (66)
"Cute little place, very clean and quiet area. We enjoyed our stay."
United States
sonya G.
Trail Lovers Getaway - walk or bike to downtown

Aparthotel in Helena

9.8 out of 10, Exceptional, (16)
"Nice place to stay that avoids the hotel vibe."
United States
Erik
$124 nightly
The price is $134
Nov 24 - Nov 25
Total with taxes and fees
Suite 32 - King Suite

Vacation Home in Helena

4.0 out of 10, (1)
"The place was clean(ish). Had a horrible smoke/musty smell. Tried asking the owner about it and it was just kind of shrugged off. I messaged the host in advance about what was available for cooking, she said everything. Got to the home and they had basically nothing for cooking. 1 pan that was bent and cut so bad you couldn’t cook with it. No measuring cups, no knives for steaks, no basic utensils, very bare minimum. "
United States
Kayla A.
Lakefront single story house on Hauser Lake

Vacation Home in Helena

10.0 out of 10, Exceptional, (14)
"This is a beautiful home that had nice amenities for our stay. It was so nice to be able to stay here during our son's multi-day soccer tryouts instead of driving back home each day. Plus, we were able to squeeze in the Winter Bazaar which was a nice treat. We enjoyed being able to bring our dog with us, too. It was our mini-vacation for the weekend. :)"
United States
Heather E
$239 nightly
The price is $258
Nov 30 - Dec 1
Total with taxes and fees
Giant View Home

Cabin in Helena

8.6 out of 10, Excellent, (7)
"Very quiet, nice place. "
United States
Rebekah
$139 nightly
The price is $150
Nov 30 - Dec 1
Total with taxes and fees
Cabin 24 - Helena Hideaway

Vacation Home in Helena

9.4 out of 10, Exceptional, (8)
"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.
$149 nightly
The price is $161
Nov 30 - Dec 1
Total with taxes and fees
Suites 35 +Up - Victorian Queen

Vacation Home in Helena

10.0 out of 10, Exceptional, (154)
"Great place to stay. Would stay there again."
United States
Deborah M.
Cozy spacious king bed suite, In the heart of Historic Helena, Montana!

Vacation Home in Helena

2.0 star property
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
Nov 25 - Nov 26
Total with taxes and fees
This cozy house has been completely remodeled inside and features three bedrooms.

Vacation Home in Clancy

10.0 out of 10, Exceptional, (117)
"Lovely place! We enjoyed our stay. "
United States
Alisa T.
$146 nightly
The price is $158
Nov 24 - Nov 25
Total with taxes and fees
Ranch House in the Elkhorn Mountains

Cabin in Jefferson City

10.0 out of 10, Exceptional, (17)
"Place is adorable with incredible views! Host has thought of all the details for an incredible stay. "
United States
Kemberlee B.
Romantic Montana A-Frame | Hot Tub & Views

Vacation Home in Helena

10.0 out of 10, Exceptional, (42)
"Wonderful views! Very well stocked!! Clean interior! Accommodating hosts! "
United States
Steph G.
A cozy getaway with lakefront access.

Aparthotel in Helena

9.4 out of 10, Exceptional, (6)
"Great place near downtown Helena."
United States
Bridgett C.
$149 nightly
The price is $161
Nov 24 - Nov 25
Total with taxes and fees
Suite 31 - Private Porch Suite

Vacation Home in Helena

10.0 out of 10, Exceptional, (11)
"Great place for the family to stay, house was very clean, and we really enjoyed the front porch."
United States
jennifer M.
Governor Leslie's Historic Home

Cottage in Helena

3.0 star property
Historic Helena Retreat - Near Dtwn & Mt Helena!
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 $134 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 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.