Title: Winston Vacation Home Rentals from CA $151: Search Top Private Vacation Homes for Rent | Expedia.ca [Hotels in Winston](https://expedia.ca/Winston-Hotels.d553248634983144235.Travel-Guide-Hotels)[Vacation Rentals in Winston](https://expedia.ca/Winston-Vacation-Rentals.d553248634983144235.Travel-Guide-VacationRentals)[Winston Car Rentals](https://expedia.ca/Car-Rentals-In-Winston.d553248634983144235.Car-Rental-Guide)[Winston Vacation Packages](https://expedia.ca/Winston.d553248634983144235.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Winston Vacation Rentals ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248634983144235&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248634983144235&startDate=2025-11-14&endDate=2025-11-16&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248634983144235&startDate=2025-11-28&endDate=2025-11-30&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248634983144235&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winston Vacation Homes ![Interior](https://images.trvl-media.com/lodging/24000000/23610000/23603400/23603383/15e16e74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/24000000/23610000/23603400/23603383/1c7f303c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/24000000/23610000/23603400/23603383/574d4d30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/24000000/23610000/23603400/23603383/e46c68fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ranch House in the Elkhorn Mountains Clancy 10/10 Exceptional (116) "Beautiful views, great hosts, serene and peaceful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) darlene h. CA $175 CA $221 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/East-Helena-Hotels-Ranch-House-In-Elkhorn-Mountains.h23603383.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76390000/76386700/76386630/a94d3f56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76390000/76386700/76386630/2ef80ea1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/77000000/76390000/76386700/76386630/456d9117.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/77000000/76390000/76386700/76386630/9701cad8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy townhouse close to Hospital & Capital Helena 10/10 Exceptional (92) "We really enjoyed our time the home was very cozy and in the perfect location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ashley B. CA $145 CA $265 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Helena-Hotels-Cozy-Townhouse-Close-To-Hospital-Capital.h76386630.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108350000/108344100/108344099/b42c7a33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, WiFi](https://images.trvl-media.com/lodging/109000000/108350000/108344100/108344099/e51629ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108350000/108344100/108344099/6f95a9cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108350000/108344100/108344099/a692bd7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### This cozy house has been completely remodeled inside and features three bedrooms. Helena 10/10 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](https://a.travel-assets.com/egds/marks/flags/us.svg) Scott O. CA $175 CA $225 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Helena-Hotels-This-Cozy-House-Has-Been-Completely-Remodeled-Inside-And-Features-Three-Bedrooms.h108344099.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/90000000/89670000/89664200/89664184/9ac85e1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89670000/89664200/89664184/44ecf2f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89670000/89664200/89664184/11517a51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi](https://images.trvl-media.com/lodging/90000000/89670000/89664200/89664184/a56ca388.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Suites 34 & 35 - Victorian Suites Helena 10/10 Exceptional (2) "Property is older but easy to get to, good location, good price and plenty of room." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $208 CA $264 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Helena-Hotels-Suites-34-35-Victorian-Suites.h89664184.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/108000000/107840000/107837800/107837715/66ffab44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/108000000/107840000/107837800/107837715/017766aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107840000/107837800/107837715/b669632d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/108000000/107840000/107837800/107837715/d88b8fff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Find Your Sanctuary at The Church Helena 10/10 Exceptional (10) "The church is charming and architecturally interesting. We loved the spacious layout. Downtown is just 2-3 blocks away. The owner is very communicative. We’d definitely stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sue CA $293 CA $617 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Helena-Hotels-Find-Your-Sanctuary-At-The-Church.h107837715.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/92000000/91570000/91562200/91562139/w903h683x60y0-45219a3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, stereo](https://images.trvl-media.com/lodging/92000000/91570000/91562200/91562139/w507h683x259y0-84958512.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91570000/91562200/91562139/w506h683x259y0-c6152df5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, travel crib, free WiFi, bed sheets](https://images.trvl-media.com/lodging/92000000/91570000/91562200/91562139/w904h683x60y0-65f02d14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Style and comfort in Helena! Easy access to any part of Helena. No cleaning fees Helena 10/10 Exceptional (50) "Cozy and very clean. I would stay here again anytime!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joelle H. CA $246 CA $303 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Helena-Hotels-Style-And-Comfort-In-Helena-Easy-Access-To-Any-Part-Of-Helena.h91562139.Hotel-Information) ![Eco-friendly cleaning products, paper towels, dining tables](https://images.trvl-media.com/lodging/109000000/108590000/108582500/108582473/39dd06c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108590000/108582500/108582473/cf777c04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/109000000/108590000/108582500/108582473/c1bda555.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/109000000/108590000/108582500/108582473/f9ab852d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Giant View Home Helena 10/10 Exceptional (13) "Loved my stay and would absolutely book again when I visit Helena next. Everything about the house and property were great, and the location is nice and quiet. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ethan K. CA $159 CA $361 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Helena-Hotels-Giant-View-Home.h108582473.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/94000000/93070000/93061100/93061024/2b1d06e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/94000000/93070000/93061100/93061024/414fcc08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/94000000/93070000/93061100/93061024/2b7396ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/94000000/93070000/93061100/93061024/53c68eab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Madison - newly remodeled, centrally located. Helena 9.4/10 Exceptional (11) "Great stay at a clean, well stocked and pretty house. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Holly S. CA $265 CA $534 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Helena-Hotels-Madison-Newly-Remodeled.h93061024.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/90000000/89670000/89664200/89664180/b00abe98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower](https://images.trvl-media.com/lodging/90000000/89670000/89664200/89664180/4c34ecbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi](https://images.trvl-media.com/lodging/90000000/89670000/89664200/89664180/8138d362.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/90000000/89670000/89664200/89664180/w959h1365x0y0-a4042c2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Suite 35 - Victorian Suite W/ Porch Helena 8.0/10 Very good (2) "Stayed here twice after picking up each of our 2 boxer puppies in Bozeman on our way back to Kalispell. Wonderful area with beautiful historic houses." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea R. CA $106 CA $151 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Helena-Hotels-Suite-35-Victorian-Suite-W-Porch.h89664180.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/90000000/89670000/89664200/89664177/0e2ec103.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower](https://images.trvl-media.com/lodging/90000000/89670000/89664200/89664177/20bbfa6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi](https://images.trvl-media.com/lodging/90000000/89670000/89664200/89664177/0440e31f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/90000000/89670000/89664200/89664177/6d092c03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Suite 34- Victorian Suite Helena 7.4/10 Good (6) "Overall we had a good time. Didn't have any issues with our stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa R. CA $106 CA $151 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Helena-Hotels-Suite-34-Victorian-Suite.h89664177.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/90000000/89670000/89664200/89664188/2d0d4ff3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/90000000/89670000/89664200/89664188/w959h1365x0y0-7ac8e25d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89670000/89664200/89664188/00f92590.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, WiFi](https://images.trvl-media.com/lodging/90000000/89670000/89664200/89664188/7c7c77a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Suites 35 +Up - Victorian Queen Helena 9.4/10 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](https://a.travel-assets.com/egds/marks/flags/us.svg) Tiffany K. CA $175 CA $225 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Helena-Hotels-Suites-35-Up-Victorian-Queen.h89664188.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-11&endDate=2025-11-12®ionId=553248634983144235&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinston-Private-Vacation-Homes.d553248634983144235-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinston-Private-Vacation-Homes.d553248634983144235-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Winston Hotel Reviews ![Best Western Helena/Capitol Hotel](//images.trvl-media.com/lodging/1000000/50000/40100/40040/4374d125_y.jpg) ### Best Western Helena/Capitol Hotel 10/10 Excellent "it was a nice property, nice rooms, excellent staff. " [](https://expedia.ca/Helena-Hotels-Jorgensons-Inn-Suites.h40040.Hotel-Information) ![Best Western Premier Helena Great Northern Hotel](//images.trvl-media.com/lodging/1000000/980000/970600/970516/23473bf8_y.jpg) ### Best Western Premier Helena Great Northern Hotel 10/10 Excellent "Great" [](https://expedia.ca/Helena-Hotels-Best-Western-Premier-Helena-Great-Northern-Hotel.h970516.Hotel-Information) ![Days Inn by Wyndham Helena](//images.trvl-media.com/lodging/1000000/30000/21600/21508/adb73f63_y.jpg) ### Days Inn by Wyndham Helena 10/10 Excellent "The room was very clean and well-appointed. Bed was super comfy. I would definitely book this hotel again. " [](https://expedia.ca/Helena-Hotels-Days-Inn-By-Wyndham-Helena.h21508.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Helena](//images.trvl-media.com/lodging/1000000/20000/19200/19156/e6191e60_y.jpg) ### La Quinta Inn & Suites by Wyndham Helena 10/10 Excellent "Adequate for the night " [](https://expedia.ca/Helena-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Helena.h19156.Hotel-Information) ![Holiday Inn Express Hotel & Suites Helena by IHG](//images.trvl-media.com/lodging/5000000/4240000/4236100/4236001/dbab0196_y.jpg) ### Holiday Inn Express Hotel & Suites Helena by IHG 10/10 Excellent "We had a wonderful stay in Helena! Jim was a staff member we would like to recognize. He was always ready and helpful at the front desk!" [](https://expedia.ca/Helena-Hotels-Holiday-Inn-Express-Hotel-Suites-Helena.h4236001.Hotel-Information) ![Delta Hotels by Marriott Helena Colonial](//images.trvl-media.com/lodging/1000000/30000/22400/22384/f437d8d4_y.jpg) ### Delta Hotels by Marriott Helena Colonial 10/10 Excellent "Beautiful stairway in the lobby. Few steps up from the last place we stayed at in Helena. This is our new favorite. We’ll be back! " [](https://expedia.ca/Helena-Hotels-Delta-Hotels-By-Marriott-Helena-Colonial.h22384.Hotel-Information) ![Baymont by Wyndham Helena](//images.trvl-media.com/lodging/1000000/20000/14400/14395/8d2b3e6d_y.jpg) ### Baymont by Wyndham Helena 10/10 Excellent "Shower/tub was clean but tub needs replaced. Pillow stains washed but still visible? However, pillows and beds were comfortable. Place was out of regular coffee except at free breakfast. We so look forward to in room coffee. Breakfast was ok and coffee was good." [](https://expedia.ca/Helena-Hotels-Baymont-By-Wyndham-Helena.h14395.Hotel-Information) ![Hampton Inn Helena](//images.trvl-media.com/lodging/1000000/900000/894600/894538/875696da_y.jpg) ### Hampton Inn Helena 10/10 Excellent "Hampton inn is a win. We always stay here Great beds. Efficient staff great breakfast And the location is handy" [](https://expedia.ca/Helena-Hotels-Hampton-Inn-Helena.h894538.Hotel-Information) ![DoubleTree by Hilton Helena Downtown](//images.trvl-media.com/lodging/1000000/50000/40100/40047/ab895621_y.jpg) ### DoubleTree by Hilton Helena Downtown 10/10 Excellent "Actually the entry way had 2 pigeons and their bird poop needed to be cleaned up. " [](https://expedia.ca/Helena-Hotels-DoubleTree-By-Hilton-Helena-Downtown.h40047.Hotel-Information) ## Find out more about Winston ## Winston Vacation Homes information | Number of reviews | 300 | | --- | --- | | Accommodation | 72 Vacation Homes | | Lowest Price | CA $151 | | Highest Price | CA $617 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [Hotels near Canyon Ferry Lake](https://www.expedia.ca/Canyon-Ferry-Lake-Hotels.0-l553248635976197408-0.Travel-Guide-Filter-Hotels) - [Guest Houses in Clancy](https://www.expedia.ca/Clancy-Guest-Houses.d6069851-aaGuestHouses.Travel-Guide-Accommodation) - [Cheap Hotels in Clancy](https://www.expedia.ca/Clancy-Hotels-Cheap-Hotels.0-0-d6069851-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Free Breakfast in Clancy](https://www.expedia.ca/Clancy-Hotels-Hotels-With-Free-Breakfast.0-0-d6069851-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) - [Spa Hotels in Clancy](https://www.expedia.ca/Clancy-Hotels-Spa-Hotel.0-0-d6069851-tSpaHotel.Travel-Guide-Filter-Hotels) - 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