Title: Chester Vacation Home Rentals from CA $324: Search Top Private Vacation Homes for Rent | Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d3000445747.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d3000445747.Travel-Guide-VacationRentals)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d3000445747.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d3000445747.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) # Chester 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 In two weeks [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=3000445747&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=3000445747&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=3000445747&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=3000445747&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chester Vacation Homes ![Exterior detail](https://images.trvl-media.com/lodging/38000000/37270000/37266700/37266607/a709c15f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, books, music library](https://images.trvl-media.com/lodging/38000000/37270000/37266700/37266607/79197ad1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/38000000/37270000/37266700/37266607/5946eefe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/38000000/37270000/37266700/37266607/7e574f2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Chester 9.8/10 Exceptional (9) "This is a great little location and we were so happy to find a place to stay in Chester. We will definitely stay here again and make sure to tell others coming through the area about it if they need a place to stay. Accommodations were great and exactly what we needed for this trip." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicole P. CA $223 CA $324 total includes taxes & fees Dec 5 - Dec 6 [](https://www.expedia.ca/Chester-Hotels-The-Great-Northern-Bed-Breakfast.h37266607.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/37000000/36470000/36462300/36462235/9810ae28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, travel crib, free WiFi, bed sheets](https://images.trvl-media.com/lodging/37000000/36470000/36462300/36462235/de1a5a49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/37000000/36470000/36462300/36462235/2c8d5a55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/37000000/36470000/36462300/36462235/5db5127f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Chester 10/10 Exceptional (23) "Great place to stay in a nice town in Montana!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Neil L. CA $223 CA $324 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Chester-Hotels-The-Homestead-2-Bedroom-House-In-The-Heart-Of-Chester.h36462235.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=2025-12-18&endDate=2025-12-19®ionId=3000445747&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%2FChester-Private-Vacation-Homes.d3000445747-aaPrivateVacationHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Private-Vacation-Homes.d3000445747-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Chester Hotel Reviews ![The Westland Suite - Historic Lodging, Contemporary Comforts](https://images.trvl-media.com/lodging/38000000/37270000/37266500/37266433/fa985b9a_y.jpg) ### The Westland Suite - Historic Lodging, Contemporary Comforts 10/10 Excellent "Westland Suite was charming and fit our needs perfectly. Four adults and two teenagers stayed and all were very comfortable. " [](https://expedia.ca/Chester-Hotels-The-Westland-Suite-Historic-Lodging.h37266433.Hotel-Information) ![The Homestead - 3 bedroom House in the Heart of Chester](https://images.trvl-media.com/lodging/37000000/36470000/36462300/36462235/9810ae28_y.jpg) ### The Homestead - 3 bedroom House in the Heart of Chester 10/10 Excellent "We enjoyed our stay so much! Patty was an excellent host, and the property was sparkling clean and well provisioned! Would stau again. " [](https://expedia.ca/Chester-Hotels-The-Homestead-2-Bedroom-House-In-The-Heart-Of-Chester.h36462235.Hotel-Information) ![Farmhouse on Hi-Line near hunting and fishing enroute to Glacier National Park ](https://images.trvl-media.com/lodging/64000000/63340000/63330300/63330204/1bc17634_y.jpg) ### Farmhouse on Hi-Line near hunting and fishing enroute to Glacier National Park 10/10 Excellent "Had a great day again. Place is ideally located, very peaceful, clean, and fully updated. Will stay again." [](https://expedia.ca/Rudyard-Hotels-Farmhouse-On-Hi-Line-Near-Hunting-And-Fishing-Enroute-To-Glacier-National-Park.h63330204.Hotel-Information) ## Find out more about Chester ## Chester Vacation Homes information | Number of reviews | 23 | | ----------------- | ---------------- | | Accommodation | 3 Vacation Homes | | Lowest Price | CA $324 | | Highest Price | CA $324 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [3 Star Hotels in Brady ](https://www.expedia.ca/3Star-Brady-Hotels.s30-0-d770577791041282048.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Joplin ](https://www.expedia.ca/3Star-Joplin-Hotels.s30-0-d6339272.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Shelby ](https://www.expedia.ca/5Star-Shelby-Hotels.s50-0-d55190.Travel-Guide-Filter-Hotels) - [Apartments in Big Sandy ](https://www.expedia.ca/Big-Sandy-Apartments.d553248634983222189-aaApartments.Travel-Guide-Accommodation) - [Luxury Hotels in Big Sandy ](https://www.expedia.ca/Big-Sandy-Hotels-Luxury-Hotel.0-0-d553248634983222189-tLuxuryHotel.Travel-Guide-Filter-Hotels) - 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