Title: Chesterfield Vacation Home Rentals from CA $238: Search Top Private Vacation Homes for Rent | Expedia.ca [Hotels in Chesterfield](https://expedia.ca/Chesterfield-Hotels.d553248634983592733.Travel-Guide-Hotels)[Vacation Rentals in Chesterfield](https://expedia.ca/Chesterfield-Vacation-Rentals.d553248634983592733.Travel-Guide-VacationRentals)[Chesterfield Car Rentals](https://expedia.ca/Car-Rentals-In-Chesterfield.d553248634983592733.Car-Rental-Guide)[Chesterfield Vacation Packages](https://expedia.ca/Chesterfield.d553248634983592733.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) # Chesterfield 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 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248634983592733&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 months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248634983592733&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=553248634983592733&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=553248634983592733&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chesterfield vacation homes ![Terrace/patio](https://images.trvl-media.com/lodging/43000000/42570000/42565000/42564987/9d8905a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/43000000/42570000/42565000/42564987/24911a22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/43000000/42570000/42565000/42564987/39f17f9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/43000000/42570000/42565000/42564987/2dbacef1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Girard [](https://www.expedia.ca/Girard-Hotels-Home-Is-On-The-Original-1926-1930-Route-66.h42564987.Hotel-Information) 10/10 Exceptional (96) "The historic house was perfect for our vacation. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelly F. CA $99 CA $238 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Girard-Hotels-Home-Is-On-The-Original-1926-1930-Route-66.h42564987.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100960000/100959700/100959686/w506h683x259y0-c518bec2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/101000000/100960000/100959700/100959686/w508h683x258y0-cb5da27d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/101000000/100960000/100959700/100959686/w506h683x259y0-b82b3b55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100960000/100959700/100959686/w507h683x259y0-b4826c30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Jerseyville [](https://www.expedia.ca/Jerseyville-Hotels-McClusky-Trail-GuesthouseConvenient-Access-To-Jerseyville.h100959686.Hotel-Information) 10/10 Exceptional (21) "Nicely appointed space, comfy beds, convenient location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mike & JoAnn H. CA $146 CA $297 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Jerseyville-Hotels-McClusky-Trail-GuesthouseConvenient-Access-To-Jerseyville.h100959686.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100410000/100408600/100408559/afa6466c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100410000/100408600/100408559/df4d5d86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/101000000/100410000/100408600/100408559/bc65b733.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/101000000/100410000/100408600/100408559/b5789be7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Carlinville [](https://www.expedia.ca/Carlinville-Hotels-The-Carlinville-Cottage.h100408559.Hotel-Information) 10/10 Exceptional (17) "This was a fantastic stay in a wonderfully clean space! We really enjoyed Carlinville cottage ans would stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Casey C. CA $303 CA $690 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Carlinville-Hotels-The-Carlinville-Cottage.h100408559.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=2025-12-28&endDate=2025-12-29®ionId=553248634983592733&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=Chesterfield%2C+Illinois%2C+United+States+of+America®ionId=553248634983592733&latLong=39.255046%2C-90.063163&adults=2&startDate=2026-03-14&d1=2026-03-14&endDate=2026-03-17&d2=2026-03-17&lodging=APARTMENT) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Chesterfield%2C+Illinois%2C+United+States+of+America®ionId=553248634983592733&latLong=39.255046%2C-90.063163&adults=2&startDate=2026-03-14&d1=2026-03-14&endDate=2026-03-17&d2=2026-03-17&lodging=VACATION_HOME) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Chesterfield%2C+Illinois%2C+United+States+of+America®ionId=553248634983592733&latLong=39.255046%2C-90.063163&adults=2&startDate=2026-03-14&d1=2026-03-14&endDate=2026-03-17&d2=2026-03-17&lodging=CABIN) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Chesterfield%2C+Illinois%2C+United+States+of+America®ionId=553248634983592733&latLong=39.255046%2C-90.063163&adults=2&startDate=2026-03-14&d1=2026-03-14&endDate=2026-03-17&d2=2026-03-17&lodging=COTTAGE) ![](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%2FChesterfield-Private-Vacation-Homes.d553248634983592733-aaPrivateVacationHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChesterfield-Private-Vacation-Homes.d553248634983592733-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Chesterfield Hotel Reviews ![Super 8 by Wyndham Jerseyville](https://images.trvl-media.com/lodging/1000000/450000/440500/440446/8d67e6ab_y.jpg) ### Super 8 by Wyndham Jerseyville 10/10 Excellent "yes" [](https://expedia.ca/Litchfield-Hotels-Super-8-By-Wyndham-Jerseyville.h440446.Hotel-Information) ![Super 8 by Wyndham Staunton](https://images.trvl-media.com/lodging/1000000/70000/62400/62339/a2a3bf94_y.jpg) ### Super 8 by Wyndham Staunton 10/10 Excellent "Both great" [](https://expedia.ca/Litchfield-Hotels-Super-8-By-Wyndham-Staunton.h62339.Hotel-Information) ![Victorian Carlinville home on Rt. 66 ](https://images.trvl-media.com/lodging/65000000/65000000/64994300/64994277/7e556213_y.jpg) ### Victorian Carlinville home on Rt. 66 10/10 Excellent "The home is exactly as described and pictured. Full kitchen with spices, oil, etc - very helpful! Central location is awesome, and you can walk to the Dollar General across the street, which has great grocery options. Beds were very, very comfortable. Lots of helpful notes around the property and extras included, including several blow dryers, etc. Would recommend." [](https://expedia.ca/Carlinville-Hotels-Victorian-Retreat-Close-To-Carlinville-Iconic-Rt-66-Square.h64994277.Hotel-Information) ![Home is on the original 1926-1930 Route 66 alignment](https://images.trvl-media.com/lodging/43000000/42570000/42565000/42564987/9d8905a5_y.jpg) ### Home is on the original 1926-1930 Route 66 alignment 10/10 Excellent "Everything was just what we needed to meet our travel needs. We felt like we were at a family members home. We were lucky to encounter the first BIG snow of the season. That did not keep us from the wedding we came to town for. They left a shovel just in case. That helped make the day. Thanks for everything!" [](https://expedia.ca/Girard-Hotels-Home-Is-On-The-Original-1926-1930-Route-66.h42564987.Hotel-Information) ![Hampton Inn by Hilton Litchfield](https://images.trvl-media.com/lodging/2000000/1380000/1374000/1373941/d92274c8_y.jpg) ### Hampton Inn by Hilton Litchfield 10/10 Excellent "Room was nice hallways are really cold. Like you are outside cold. Rooms have a lot of outside noise. Staff is very helpful. Breakfast was good." [](https://expedia.ca/Litchfield-Hotels-Hampton-Inn-Litchfield.h1373941.Hotel-Information) ![Carlin Villa Motel](https://images.trvl-media.com/lodging/12000000/11400000/11392600/11392556/52edb97a_y.jpg) ### Carlin Villa Motel 10/10 Excellent " Very quiet and clean. A great place to stay for a nostalgic stay along old Route 66." [](https://expedia.ca/Litchfield-Hotels-Carlin-Villa-Motel.h11392556.Hotel-Information) ![The Carlinville Cottage](https://images.trvl-media.com/lodging/101000000/100410000/100408600/100408559/afa6466c_y.jpg) ### The Carlinville Cottage 10/10 Excellent "Beautiful home, well appointed. Very accommodating host, we have rented this home many times and keep coming back!" [](https://expedia.ca/Carlinville-Hotels-The-Carlinville-Cottage.h100408559.Hotel-Information) ![Cozy studio located in small town America, Bunker Hill, IL. ](https://images.trvl-media.com/lodging/107000000/106750000/106748200/106748150/1da5c07a_y.jpg) ### Cozy studio located in small town America, Bunker Hill, IL. 10/10 Excellent "Lovely, comfortable and quiet loft. Extremely clean and softly decorated. Host provided every amenity one might need. Very thankful for the water in frig. We would gladly stay again if anywhere near the area. Located within wslking distance of several restaurants. Sage House was excellent. Breakfast at Sally's perfect." [](https://expedia.ca/Bunker-Hill-Hotels-Cozy-Studio-Located-In-Small-Town-America.h106748150.Hotel-Information) ![McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton](https://images.trvl-media.com/lodging/101000000/100960000/100959700/100959686/w506h683x259y0-c518bec2_y.jpg) ### McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton 10/10 Excellent "Very clean, newly remodeled, very well stocked." [](https://expedia.ca/Jerseyville-Hotels-McClusky-Trail-GuesthouseConvenient-Access-To-Jerseyville.h100959686.Hotel-Information) ## Find out more about Chesterfield ## Chesterfield Vacation Homes information | Number of reviews | 132 | | ----------------- | ---------------- | | Accommodation | 6 Vacation Homes | | Lowest Price | CA $238 | | Highest Price | CA $690 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Apartments in Benld ](https://www.expedia.ca/Benld-Apartments.d553248634983372757-aaApartments.Travel-Guide-Accommodation) - [Spa Hotels in Bethalto ](https://www.expedia.ca/Bethalto-Hotels-Spa-Hotel.0-0-d79380-tSpaHotel.Travel-Guide-Filter-Hotels) - [Bethalto Hotels ](https://www.expedia.ca/Bethalto-Hotels.d79380.Travel-Guide-Hotels) - [Brighton Hotels ](https://www.expedia.ca/Brighton-Hotels.d553248634983484440.Travel-Guide-Hotels) - [Bunker Hill Hotels ](https://www.expedia.ca/Bunker-Hill-Hotels.d553248634983416591.Travel-Guide-Hotels) - 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