Title: Winston Vacation Home Rentals from CA $293: Search Top Private Vacation Homes for Rent | Expedia.ca [Hotels in Winston](https://expedia.ca/Winston-Hotels.d553248634983181173.Travel-Guide-Hotels)[Vacation Rentals in Winston](https://expedia.ca/Winston-Vacation-Rentals.d553248634983181173.Travel-Guide-VacationRentals)[Winston Car Rentals](https://expedia.ca/Car-Rentals-In-Winston.d553248634983181173.Car-Rental-Guide)[Winston Vacation Packages](https://expedia.ca/Winston.d553248634983181173.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.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 [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248634983181173&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) In two weeks [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248634983181173&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=553248634983181173&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=553248634983181173&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winston vacation homes ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/60000000/59290000/59282600/59282599/556b3042.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/60000000/59290000/59282600/59282599/6b7ef516.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/60000000/59290000/59282600/59282599/c9663579.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/60000000/59290000/59282600/59282599/bf5bf8a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hamilton Getaway -Entire House in DT Hamilton [](https://www.expedia.ca/Hamilton-Hotels-Hamilton-Getaway-Entire-House-In-DT-Hamilton.h59282599.Hotel-Information) Hamilton 9.8/10 Exceptional (53) "Great stay-" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) IRENE H. CA $218 CA $324 total includes taxes & fees Jan 10 - Jan 11, 2026 [](https://www.expedia.ca/Hamilton-Hotels-Hamilton-Getaway-Entire-House-In-DT-Hamilton.h59282599.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/93000000/92200000/92199100/92199006/afde3ff3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, internet](https://images.trvl-media.com/lodging/93000000/92200000/92199100/92199006/af7b7b18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bathroom](https://images.trvl-media.com/lodging/93000000/92200000/92199100/92199006/4458d1a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/93000000/92200000/92199100/92199006/6354e99f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Piper's Place - 2 Bedroom House in DT Hamilton [](https://www.expedia.ca/Hamilton-Hotels-Pipers-Place-2-Bedroom-House-In-DT-Hamilton.h92199006.Hotel-Information) Hamilton 9.2/10 Wonderful (13) "House was nicely updated, conveniently located; perfect for a landing spot while we were visiting family." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Margie B. CA $192 CA $293 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Hamilton-Hotels-Pipers-Place-2-Bedroom-House-In-DT-Hamilton.h92199006.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/71000000/70990000/70987100/70987079/38f85f49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/71000000/70990000/70987100/70987079/2f548acd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/71000000/70990000/70987100/70987079/d937ab05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/71000000/70990000/70987100/70987079/dcd69499.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfortable Two-Story Family Home in Picturesque Small Town USA [](https://www.expedia.ca/Hamilton-Hotels-Comfortable-Two-Story-Family-Home-In-Picturesque-Small-Town-USA.h70987079.Hotel-Information) Hamilton 9.8/10 Exceptional (111) "We adored this place! So clean, so cute and so inviting! Would definitely stay there again if in the area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) EUNICE L. CA $222 CA $363 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Hamilton-Hotels-Comfortable-Two-Story-Family-Home-In-Picturesque-Small-Town-USA.h70987079.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/114000000/113150000/113142000/113141945/54e4edb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113150000/113142000/113141945/4341e4a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/114000000/113150000/113142000/113141945/w1202h1226x0y6-3271ba32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113150000/113142000/113141945/7964615a_edited_61e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1920s Restored Home-walk to MSQC shops, Quilt Town USA [](https://www.expedia.ca/Hamilton-Hotels-1920s-Restored-Home-Walk-To-MSQC-Shops.h113141945.Hotel-Information) Hamilton 10/10 Exceptional (7) "Very clean, lots of room, well furnished kitchen. It was like being in a new model home. Very close to the quilt shops, easy walk. Great communication with the owners! Check-in was a breeze! Would definitely stay there again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kyrenda L. CA $334 CA $580 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/Hamilton-Hotels-1920s-Restored-Home-Walk-To-MSQC-Shops.h113141945.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=2026-01-03&endDate=2026-01-04®ionId=553248634983181173&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Apartments [](https://www.expedia.ca/Hotel-Search?destination=Winston%2C+Missouri%2C+United+States+of+America®ionId=553248634983181173&latLong=39.870004%2C-94.139947&adults=2&startDate=2026-03-20&d1=2026-03-20&endDate=2026-03-23&d2=2026-03-23&lodging=APARTMENT) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Winston%2C+Missouri%2C+United+States+of+America®ionId=553248634983181173&latLong=39.870004%2C-94.139947&adults=2&startDate=2026-03-20&d1=2026-03-20&endDate=2026-03-23&d2=2026-03-23&lodging=CABIN) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Winston%2C+Missouri%2C+United+States+of+America®ionId=553248634983181173&latLong=39.870004%2C-94.139947&adults=2&startDate=2026-03-20&d1=2026-03-20&endDate=2026-03-23&d2=2026-03-23&lodging=COTTAGE) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Winston%2C+Missouri%2C+United+States+of+America®ionId=553248634983181173&latLong=39.870004%2C-94.139947&adults=2&startDate=2026-03-20&d1=2026-03-20&endDate=2026-03-23&d2=2026-03-23&lodging=VACATION_HOME) ![](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.d553248634983181173-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.d553248634983181173-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Winston Hotel Reviews ![Red Roof Inn Cameron](https://images.trvl-media.com/lodging/1000000/40000/40000/39991/917e85d1_y.jpg) ### Red Roof Inn Cameron 10/10 Excellent "Comfortable small hotel " [](https://expedia.ca/St-Joseph-Hotels-Red-Roof-Inn-Cameron.h39991.Hotel-Information) ![Charming 1-bedroom Guest Home with WiFi, AC in delightful Gallatin](https://images.trvl-media.com/lodging/110000000/109420000/109414700/109414671/f709f30d_y.jpg) ### Charming 1-bedroom Guest Home with WiFi, AC in delightful Gallatin 10/10 Excellent "The host was quick and efficient in all correspondence. The place was cute and clean!" [](https://expedia.ca/Gallatin-Hotels-Charming-1-Bedroom-Guest-Home-With-WiFi.h109414671.Hotel-Information) ![The Farm House - Have Fun on the Farm This Fall!](https://images.trvl-media.com/lodging/107000000/106800000/106793500/106793415/e617de81_y.jpg) ### The Farm House - Have Fun on the Farm This Fall! 10/10 Excellent "We werebin town for a quick wedding trip. This house was perfect for our group of 6 adults. The house was spacious, welcoming, clean, and accommodating. One of our party is handicapped. We had zero issues. The host was quick to respond. Our trip was definitely a 10/10\. " [](https://expedia.ca/Osborn-Hotels-The-Farm-House.h106793415.Hotel-Information) ![Quality Inn Cameron](https://images.trvl-media.com/lodging/1000000/50000/42200/42192/5baaa282_y.jpg) ### Quality Inn Cameron 10/10 Excellent "efficient check in. VERY CLEAN and quiet. Right next door to 24 Wendys, McDonalds, and huge gas station. Washer 75 cents and dryer $1\. Walmart near by." [](https://expedia.ca/St-Joseph-Hotels-Quality-Inn-Cameron.h42192.Hotel-Information) ![1920s Restored Home-walk to MSQC shops, Quilt Town USA](https://images.trvl-media.com/lodging/114000000/113150000/113142000/113141945/54e4edb9_y.jpg) ### 1920s Restored Home-walk to MSQC shops, Quilt Town USA 10/10 Excellent "The kitchen was well stocked with essential utensils. The fridge is amazing - large, with ice maker. We enjoyed the open flow of the dining/lounge/living room area. We even had space to open a folding table to do a jigsaw puzzle. The beds are comfortable and rooms nicely decorated. Bathrooms are upstairs and down, so very convenient. We will be back! " [](https://expedia.ca/Hamilton-Hotels-1920s-Restored-Home-Walk-To-MSQC-Shops.h113141945.Hotel-Information) ![Days Inn by Wyndham Cameron](https://images.trvl-media.com/lodging/1000000/50000/42200/42165/602776a9_y.jpg) ### Days Inn by Wyndham Cameron 10/10 Excellent "Yes.very good" [](https://expedia.ca/St-Joseph-Hotels-Days-Inn-By-Wyndham-Cameron.h42165.Hotel-Information) ![Motel 6 Cameron, MO](https://images.trvl-media.com/lodging/10000000/10000000/9992800/9992788/35d22ebd_y.jpg) ### Motel 6 Cameron, MO 10/10 Excellent "Very clean and comfortable. Great staff. " [](https://expedia.ca/Cameron-Hotels-Motel-6-Cameron.h9992788.Hotel-Information) ![Super 8 by Wyndham Cameron](https://images.trvl-media.com/lodging/1000000/860000/855500/855452/fbe988e4_y.jpg) ### Super 8 by Wyndham Cameron 10/10 Excellent "Great hotel and staff, excellent rooms and beds, breakfast bar and coffee the best" [](https://expedia.ca/St-Joseph-Hotels-Super-8-By-Wyndham-Cameron.h855452.Hotel-Information) ![SureStay Hotel by Best Western Cameron](https://images.trvl-media.com/lodging/1000000/20000/10500/10417/b317db33_y.jpg) ### SureStay Hotel by Best Western Cameron 10/10 Excellent "Comfy bed. Good breakfast" [](https://expedia.ca/Cameron-Hotels-SureStay-Hotel-By-Best-Western-Cameron.h10417.Hotel-Information) ## Find out more about Winston ## Winston Vacation Homes information | Number of reviews | 180 | | ----------------- | ----------------- | | Accommodation | 15 Vacation Homes | | Lowest Price | CA $293 | | Highest Price | CA $580 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [4 Star Hotels in Holt ](https://www.expedia.ca/4Star-Holt-Hotels.s40-0-d553248634983503554.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Cameron ](https://www.expedia.ca/5Star-Cameron-Hotels.s50-0-d6533.Travel-Guide-Filter-Hotels) - [Amity Hotels ](https://www.expedia.ca/Amity-Hotels.d553248634983263244.Travel-Guide-Hotels) - [Cheap Hotels in Bethany ](https://www.expedia.ca/Bethany-Hotels-Cheap-Hotels.0-0-d6897-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Bethany ](https://www.expedia.ca/Bethany-Hotels-Luxury-Hotel.0-0-d6897-tLuxuryHotel.Travel-Guide-Filter-Hotels) - 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