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Winston Holiday Rentals

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Our top choices for Winston holiday rentals

1. Ranch house in the Elkhorn Mountains

Ranch house in the Elkhorn Mountains
Clancy
9.8 out of 10, Exceptional, (134 reviews)
"The area is nice and the ranch house was good."
United States
justin p.
The price is NZ$285
includes taxes & fees
16 Nov - 17 Nov
Ranch house in the Elkhorn Mountains

2. Lee's apartment building on Saddle Mountain

Lee's apartment building on Saddle Mountain
Clancy
10.0 out of 10, Exceptional, (72 reviews)
"Very friendly and welcoming. We enjoyed every minute of our stay."
United States
Kiersten J.
The price is NZ$389
includes taxes & fees
22 Nov - 23 Nov
Lee's apartment building on Saddle Mountain

3. SADDLE MOUNTAIN ESCAPE

SADDLE MOUNTAIN ESCAPE
Clancy
10.0 out of 10, Exceptional, (47 reviews)
"We only stayed one night, but I really wish we could’ve stayed more. It was so comfortable and relaxing. All the amenities were provided.And the owners are conscientious and kind. Can’t wait to plan my next trip there with my daughters for a girls weekend"
United States
Paula T.
The price is NZ$455
includes taxes & fees
15 Nov - 16 Nov
SADDLE MOUNTAIN ESCAPE

4. Cozy townhouse close to Hospital & Capital

Cozy townhouse close to Hospital & Capital
Helena
10.0 out of 10, Exceptional, (119 reviews)
"Great little spacious place that was perfect for our trip"
United States
Gennie W.
The price is NZ$350
includes taxes & fees
15 Nov - 16 Nov
Cozy townhouse close to Hospital & Capital

5. Luxury Home with Movie Room - right outside of Helena

Luxury Home with Movie Room - right outside of Helena
Clancy
10.0 out of 10, Exceptional, (22 reviews)
"Beautiful property, spotless and great location. Would definitely stay again."
United States
Christy P.
The price is NZ$372
includes taxes & fees
15 Nov - 16 Nov
Luxury Home with Movie Room - right outside of Helena

6. Lee's Helena Hideout

Lee's Helena Hideout
Helena
9.8 out of 10, Exceptional, (48 reviews)
"This is a great place to stay that’s close to most everything in Helena. It had everything our family of four needed and Debbie is great to communicate with. Highly recommended!!"
United States
Amy C.
Lee's Helena Hideout

7. 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, (88 reviews)
"This place is super clean and modern. Very nice stay!!"
United States
RON D.
The price is NZ$364
includes taxes & fees
15 Nov - 16 Nov
Style and comfort in Helena! Easy access to any part of Helena. No cleaning fees

8. Apartment next to Cathedral in Historic Downtown Helena

Apartment next to Cathedral in Historic Downtown Helena
Helena
9.2 out of 10, Wonderful, (48 reviews)
"A clean, charming, comfy place to stay next door the the beautiful Cathedral of St. Helena. It was a perfect fit for our family!"
United States
Sara M.
The price is NZ$402
includes taxes & fees
23 Nov - 24 Nov
Apartment next to Cathedral in Historic Downtown Helena

9. 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, (99 reviews)
"Nice cozy location in Helena, with convenient access to nearby points of interest."
United States
Richard K.
The price is NZ$341
includes taxes & fees
19 Nov - 20 Nov
Helena Townhouse next to Skelton Park (Dog and kid friendly)

10. 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, (16 reviews)
"Great place to stay. "
United States
Mark N.
The price is NZ$274
includes taxes & fees
16 Nov - 17 Nov
Trails, Tails & Town – Pet-Friendly Stay Near It All

11. LOVELY 2 Bedroom Fully Furnished w/ Laundry

LOVELY 2 Bedroom Fully Furnished w/ Laundry
Helena
9.8 out of 10, Exceptional, (19 reviews)
"Great stay! I would stay again. Great location to utilize the hot springs!!"
United States
Alisha H.
The price is NZ$490
includes taxes & fees
15 Nov - 16 Nov
LOVELY 2 Bedroom Fully Furnished w/ Laundry

12. Family Retreat- Sauna, Arcade, Gym & Message Chair

Family Retreat- Sauna, Arcade, Gym & Message Chair
Helena
10.0 out of 10, Exceptional, (3 reviews)
"The house was amazing! Our family enjoyed the kid friendly setup and all the fun things the house had to offer. We will definitely stay again when we return in the future."
United States
Justin D.
The price is NZ$1,236
includes taxes & fees
17 Nov - 18 Nov
Family Retreat- Sauna, Arcade, Gym & Message Chair

13. PERFECT 2 bedroom, 1 bath Condo

PERFECT 2 bedroom, 1 bath Condo
Helena
9.8 out of 10, Exceptional, (44 reviews)
"Great place."
United States
Russ B.
PERFECT 2 bedroom, 1 bath Condo

14. Suite 33 - Queen Suite W/ Walk-In Shower

Suite 33 - Queen Suite W/ Walk-In Shower
Helena
9.4 out of 10, Exceptional, (9 reviews)
"This place is pretty great, and had been remodeled nicely. Perfect for a few days!"
United States
Jessica B.
The price is NZ$269
includes taxes & fees
8 Dec - 9 Dec
Suite 33 - Queen Suite W/ Walk-In Shower

15. Find Your Sanctuary at The Church

Find Your Sanctuary at The Church
Helena
10.0 out of 10, Exceptional, (15 reviews)
"Great stay"
United States
David Y.
The price is NZ$766
includes taxes & fees
15 Nov - 16 Nov
Find Your Sanctuary at The Church

16. Secluded Montana A-Frame with Hot Tub and Views

Secluded Montana A-Frame with Hot Tub and Views
Jefferson City
10.0 out of 10, Exceptional, (31 reviews)
"We had a wonderful and relaxing time. This place is extremely clean and comfortable, very private and beautiful sceneries. "
United States
Anonymous traveller
The price is NZ$1,379
includes taxes & fees
26 Nov - 27 Nov
Secluded Montana A-Frame with Hot Tub and Views

17. Spacious artist's studio loft apartment with view

Spacious artist's studio loft apartment with view
Helena
9.8 out of 10, Exceptional, (10 reviews)
"Wonderful place to stay!"
United States
Raquel W.
The price is NZ$441
includes taxes & fees
15 Nov - 16 Nov
Spacious artist's studio loft apartment with view

18. Cabin 23 - Hunters Haven

Cabin 23 - Hunters Haven
Helena
9.4 out of 10, Exceptional, (3 reviews)
"It was a great stay. The cabin is a little small, next time we will get a booger cabin. We lived our stay"
United States
Valerie L.
The price is NZ$269
includes taxes & fees
15 Nov - 16 Nov
Cabin 23 - Hunters Haven

19. Helena Forest Hideout w/ Hot Tub Near Downtown

Helena Forest Hideout w/ Hot Tub Near Downtown
Helena
9.6 out of 10, Exceptional, (17 reviews)
"Beautiful location, scenery"
United States
Rhonda H.
The price is NZ$768
includes taxes & fees
15 Nov - 16 Nov
Helena Forest Hideout w/ Hot Tub Near Downtown

20. Suites 35 +Up - Victorian Queen

Suites 35 +Up - Victorian Queen
Helena
9.4 out of 10, Exceptional, (13 reviews)
"Perfect stop!"
United States
Kathy M.
The price is NZ$314
includes taxes & fees
16 Nov - 17 Nov
Suites 35 +Up - Victorian Queen
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 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, 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 NZ$285 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 spacious king bed suite, In the heart of Historic Helena, Montana!: This holiday home rental outside of Winston is located in the mountains, and has a fireplace, a selection of books and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave and a coffee maker.

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 Montana Historical Society Museum.

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.