Holiday Rentals in Winston

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Winston holiday rentals

Cabin in Townsend

Mountain Silo #7
10.0 out of 10, Exceptional, (5)
"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.
The price is €339
includes taxes & fees
4 Jan - 5 Jan
Mountain Silo #7

Cabin in Townsend

Mountain Sio #6
10.0 out of 10, Exceptional, (1)
"Location awesome and clean cabin "
United States
Meghan J.
The price is €349
includes taxes & fees
4 Jan - 5 Jan
Mountain Sio #6
10.0 out of 10, Exceptional, (21)
"Very cute cabin and property. Enjoyed our time."
United States
Amanda F.
The price is €346
includes taxes & fees
6 Jan - 7 Jan
Cozy cabin nestled beside a spring-fed pond&hobby farm in the Elkhorn Mountains
10.0 out of 10, Exceptional, (95)
"Cute little place, very clean and comfortable! "
United States
Jodi B.
The price is €182
includes taxes & fees
3 Jan - 4 Jan
Cozy townhouse close to Hospital & Capital

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.
The price is €226
includes taxes & fees
3 Jan - 4 Jan
SADDLE MOUNTAIN ESCAPE
10.0 out of 10, Exceptional, (1)
"This sweet lodging was very clean, comfortable and just as described in the website. It is a very quiet neighborhood. The hostess was quick to respond to questions, being attentive and available. I would highly recommend this place for a small group or individual staying in Helena."
United States
Tom R.
The price is €132
includes taxes & fees
4 Jan - 5 Jan
Adorable 2-bedroom cottage in wonderful Helena for a quiet and relaxing stay.
10.0 out of 10, Exceptional, (64)
"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.
The price is €199
includes taxes & fees
2 Feb - 3 Feb
Lee's apartment building on saddle mountain

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.
The price is €212
includes taxes & fees
3 Jan - 4 Jan
Lee's Helena Hideout
2.0 star property
The price is €73
includes taxes & fees
2 Feb - 3 Feb
Great place to crash after a Montana adventure!
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.
The price is €90
includes taxes & fees
3 Jan - 4 Jan
Cabin 22 - The Movie Cabin
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.
The price is €141
includes taxes & fees
4 Jan - 5 Jan
This cozy house has been completely remodeled inside and features three bedrooms.

Aparthotel in Helena

Suite 29 - Modern Suite
9.4 out of 10, Exceptional, (3)
"A wonderful place in a wonderful location, walking distance to downtown and a very short walk to hiking trails. The place had everything we needed and was in a quiet neighborhood. The place was clean and well equipped. We look forward to returning."
United States
Roger H.
Suite 29 - Modern Suite
9.8 out of 10, Exceptional, (8)
"We enjoyed this "
United States
Mary L.
The price is €184
includes taxes & fees
3 Jan - 4 Jan
Spacious artist's studio loft apartment with view
9.6 out of 10, Exceptional, (28)
"The place was very clean and had all the amenities needed. "
United States
Carlos O.
The price is €271
includes taxes & fees
3 Jan - 4 Jan
PERFECT 2 bedroom, 1 bath Condo
10.0 out of 10, Exceptional, (2)
"Great stay, the hosts made us feel very at home! They pay attention to all the details. It was the perfect place to stay when we moved to Helena."
United States
Bryce W.
The price is €166
includes taxes & fees
21 Jan - 22 Jan
Cozy studio with modern kitchen in unit laundry and AC close to hiking trails.

Holiday Home in Helena

Find Your Sanctuary at The Church
2.0 star property
10.0 out of 10, Exceptional, (10)
"It was a beautiful place to stay! The Neighborhood was great The location was so close to downtown The house looked just as the pictures did online! We didn't want to leave. "
United States
Wendy M.
The price is €386
includes taxes & fees
4 Jan - 5 Jan
Find Your Sanctuary at The Church
10.0 out of 10, Exceptional, (56)
" Wry quaint area, comfy beds, and the hosts went above and beyond. "
United States
Stefanie C.
The price is €167
includes taxes & fees
18 Jan - 19 Jan
Helena Townhouse next to Skelton Park (Dog and kid friendly)
10.0 out of 10, Exceptional, (54)
"A great home to stay in Helena! This is our second annual stay and we love it Thank you for providing a clean and cozy place!!"
United States
Amy A.
The price is €189
includes taxes & fees
11 Jan - 12 Jan
Style and comfort in Helena! Easy access to any part of Helena. No cleaning fees
9.0 out of 10, Wonderful, (33)
"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.
The price is €242
includes taxes & fees
5 Jan - 6 Jan
Apartment next to Cathedral in Historic Downtown Helena

Holiday Home in Helena

Suites 34 & 35 - Victorian Suites
10.0 out of 10, Exceptional, (3)
"Pet friendly and rooms are large. Plenty of room with the bedrooms upstairs and great location. Good location and walking friendly."
United States
Donna F.
The price is €164
includes taxes & fees
2 Feb - 3 Feb
Suites 34 & 35 - Victorian Suites
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winston Hotel Reviews

Find out more about Winston

Everything you need to know about Winston holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winston holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winston holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winston holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winston holiday rentals we have selected for you start as low as €90 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winston rentals

At Expedia, we put the best Winston holiday 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 holiday.

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 holiday rentals in Winston?

Yes, there are holiday rentals close to the most popular sights in Winston, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winston has to offer?

Cozy townhouse close to Hospital & Capital: This holiday 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 wider area, you’ll find Canyon Ferry Wildlife Management Area and Hauser Dam.

What are holiday rentals like in Winston?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winston. Holiday rentals offer amenities like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for a small group gathering.