Winston Holiday Rentals

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Holiday Rentals in Winston

Tizer Botanic Gardens Cabin 1/2 way between Yellowstone & Glacier National Parks
10.0 out of 10, Exceptional, (144)
"Our family enjoyed the gardens and Bevla was a gracious host. The cabin, the creek, and the gardens were just what we needed for the weekend. Thank you."
The price is NZ$265
includes taxes & fees
10 Jun - 11 Jun
Tizer Botanic Gardens Cabin 1/2 way between Yellowstone & Glacier National Parks
Cozy townhouse close to Hospital & Capital
10.0 out of 10, Exceptional, (38)
"Was perfect"
The price is NZ$333
includes taxes & fees
30 Jun - 1 Jul
Cozy townhouse close to Hospital & Capital
Cozy spacious king bed suite, In the heart of Historic Helena, Montana!
10.0 out of 10, Exceptional, (93)
"Excellent location within walking distance of good eateries, historic Last Chance Gulch, Great Northern district and Centennial Park. Very clean and plenty of linens. Wonderful walk in shower. For someone in her 80’s the distance from parking area to lodging entrance and 5 steps up to entrance, without handrail, was a challenge when carrying in luggage or heavy bags. Also, the lack of any table with chair for computer work or eating breakfast was a problem. Even a small coffee table would help....
Cozy spacious king bed suite, In the heart of Historic Helena, Montana!
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Style and comfort in Helena! Easy access to any part of Helena
10.0 out of 10, Exceptional, (12)
"Lovely home, with every detail on point! Beautiful, comfortable and clean The home owner has done a wonderful job with everything from the decor to the furniture to the linens and towels. The beds are very comfortable and cozy. They even have a drawer in the bathroom with items “maybe forgotten” which was an unexpected touch. We’d love to stay in this property again! Can’t say enough good things about it! Bravo homeowner, bravo!"
The price is NZ$435
includes taxes & fees
9 Jun - 10 Jun
Style and comfort in Helena! Easy access to any part of Helena
Giant View Home Summa
10.0 out of 10, Exceptional, (11)
"We visited a friend in Helena for a long weekend. The home was clean and as expected. Nice new appliances and well stocked kitchen. We had a question on regulating the electric fireplace, and the property manager promptly responded to our questions. Would definitely stay here again!"
Giant View Home Summa
Little House - Trails & Town 5 minute walk!
9.4 out of 10, Exceptional, (23)
"Super clean rental that was very relaxing to stay at. Tile shower was nice. Bed was more comfy than the one i have at home. A couple blocks away from breakfast & coffee at Greatful Bread. Communication from the host was easy & straight-forward."
The price is NZ$332
includes taxes & fees
13 Jun - 14 Jun
Little House - Trails & Town 5 minute walk!
Ranch House in the Elkhorn Mountains
9.8 out of 10, Exceptional, (84)
"Our stay at this cozy ranch house had wonderful views. We were able to walk around the property unobstructed. At dusk and dawn, we were able to see the elk that hang around this area."
The price is NZ$258
includes taxes & fees
9 Jun - 10 Jun
Ranch House in the Elkhorn Mountains
Montana living with Hot tub!
10.0 out of 10, Exceptional, (6)
"Just a great place to stay. A Beautiful house and property. Everything worked flawlessly. All the equipment and kitchen utensils are there to there for a perfect stay. The bedrooms in the basement are not furnished so it is not a 6 bedroom accommodation, but loved having the 3rd bathroom downstairs. Good communication with owner. Hope you enjoy it as much as we did."
Montana living with Hot tub!
Family Friendly Grama House
10.0 out of 10, Exceptional, (7)
"Shirley was very flexible and accommodating with our changing needs. Our stay was lovely. Thank you Shirley!"
Family Friendly Grama House
Modern Victorian - walk to downtown and trails!
10.0 out of 10, Exceptional, (20)
"Really enjoyed the physical property. Unit is on property of a main house that is timeless. The unit is the mini-me version. Security is ideal by location on property. Noise is non existent. Separate quarters upstairs with a bath/shower maintains the integrity of the building along with rock walls. Highly recommend this property. Walk to all the fun, breakfast and groceries within 5-10 min."
The price is NZ$377
includes taxes & fees
10 Jun - 11 Jun
Modern Victorian - walk to downtown and trails!
Traveler's Nest - Mt. Ascension
9.2 out of 10, Wonderful, (11)
"Clean and exactly as described. Cozy loft with incredible Helena view. Caroline and Tyler were so nice to us"
The price is NZ$352
includes taxes & fees
13 Jun - 14 Jun
Traveler's Nest - Mt. Ascension
Historic 1886 House locate convienently
9.8 out of 10, Exceptional, (13)
"It was a great house. Dining area and kitchen 10/10!!! The whole house was super charming. "
Historic 1886 House locate convienently
Birders delight! Beautiful hiking! Mountain biking! Fishing!
9.8 out of 10, Exceptional, (17)
"We enjoyed our stay!"
Birders delight! Beautiful hiking! Mountain biking! Fishing!
Rustic cabin with lake views.
9.6 out of 10, Exceptional, (25)
"Very clean"
The price is NZ$212
includes taxes & fees
16 Jun - 17 Jun
Rustic cabin with lake views.
Trail Lovers Getaway - walk or bike to downtown
10.0 out of 10, Exceptional, (37)
"I have family in Helena and visit often. I've rented various places through VRBO and I have to say that this is one of my favorites. The apartment was comfortable, clean and thoughtfully stocked (thanks for the Q-tips and Kleenex). Perhaps the best part is the neighborhood. This apartment is located on a street that is really a paved alley. The older homes are squeezed in together in every possible way. They are in all stages of repair and everyone has a project--clearly labors of love for the...
Trail Lovers Getaway - walk or bike to downtown
The west shore getaway on Canyon Ferry.
10.0 out of 10, Exceptional, (30)
"This was a lovely place to rest, relax, and recharge. The house is well stocked. We enjoyed the deck, water, and local hiking. Our only concern was the lack of phone service in case of an emergency."
The west shore getaway on Canyon Ferry.
Treasure State Cottage - centrally located
10.0 out of 10, Exceptional, (5)
"Inexpensive property, exactly what we needed. Close to everything. Check in was a breeze."
Treasure State Cottage - centrally located
Central Hub - the heart of Helena
9.6 out of 10, Exceptional, (33)
"We really enjoyed our stay."
Central Hub - the heart of Helena
Charming 2 Bed - Mt Ascension
9.6 out of 10, Exceptional, (14)
"Charming, clean and well appointed home in downtown Helena. Highly recommend :-)"
Charming 2 Bed - Mt Ascension
Hayes House 1/2 block from trail
9.6 out of 10, Exceptional, (4)
"Stayed a few days to work remote and enjo"
The price is NZ$352
includes taxes & fees
10 Jun - 11 Jun
Hayes House 1/2 block from trail
Don't see what you're looking for?
See all available properties in Winston
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.

Other types of properties in Winston you may be interested in

Baymont by Wyndham Helena
2.5 star property
8.4 out of 10, Very good, (1146)
"Great bed and shower. Area around the hotel was sketchy, but felt safe within the hotel. Loved the carpeting in the rooms as well as the cleanliness throughout the common areas."
The price is NZ$152
includes taxes & fees
16 Jun - 17 Jun
Baymont by Wyndham Helena
La Quinta Inn & Suites by Wyndham Helena
2.5 star property
7.6 out of 10, Good, (1010)
"Clean room, nice pool, comfy beds. Run down hotel but decent for the price! "
The price is NZ$196
includes taxes & fees
16 Jun - 17 Jun
La Quinta Inn & Suites by Wyndham Helena
Fairfield Inn & Suites by Marriott Helena
2.5 star property
8.6 out of 10, Excellent, (498)
"The property seemed noisy with not enough insulation between the walls and floors. Otherwise, everything was comfortable and clean."
The price is NZ$220
includes taxes & fees
23 Jun - 24 Jun
Fairfield Inn & Suites by Marriott 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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Winston holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Winston. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Winston. Seeing all the best attractions is bound to make you fall in love with Winston. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Winston short-term rentals, that won’t be hard to do.

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 Montana State Capitol and Cathedral of St. Helena.

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.

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