Title: Chesterfield Vacation Rentals from CA $173: Short-Term Rentals for 2026 | Expedia.ca

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## Check prices for these dates

In two weeks

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=553248634983592733&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=553248634983592733&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 26 - Jun 28](https://www.expedia.ca/Hotel-Search?regionId=553248634983592733&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 24 - Jul 26](https://www.expedia.ca/Hotel-Search?regionId=553248634983592733&startDate=2026-07-24&endDate=2026-07-26&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 rentals

![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/101000000/100960000/100959700/100959686/w504h683x260y0-fa59f152.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100960000/100959700/100959686/w506h683x259y0-d3f94072.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/101000000/100960000/100959700/100959686/w507h683x259y0-ec4425e3.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/w506h683x259y0-c518bec2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton

[](https://www.expedia.ca/Jerseyville-Hotels-McClusky-Trail-GuesthouseConvenient-Access-To-Jerseyville.h100959686.Hotel-Information)

Jerseyville

10/10

Exceptional

(22 reviews)

"We had a wonderful New Year’s Eve stay, everything was clean and as described. The space is very nicely renovated and decorated, highly recommended."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Valerie L.

CA $148

CA $306 total

includes taxes & fees

Apr 6 - Apr 7

[](https://www.expedia.ca/Jerseyville-Hotels-McClusky-Trail-GuesthouseConvenient-Access-To-Jerseyville.h100959686.Hotel-Information)

![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121830000/121829800/121829706/3bec06b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/122000000/121830000/121829800/121829706/803e5f8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121830000/121829800/121829706/a65ed3d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121830000/121829800/121829706/91f85310.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Light Filled Loft on Town Square

[](https://www.expedia.ca/Carlinville-Hotels-Light-Filled-Loft-On-Town-Square.h121829706.Hotel-Information)

Carlinville

10/10

Exceptional

(9 reviews)

"The loft was amazing as well as the views looking out to the town square!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Gerry G.

CA $314

CA $463 total

includes taxes & fees

Apr 12 - Apr 13

[](https://www.expedia.ca/Carlinville-Hotels-Light-Filled-Loft-On-Town-Square.h121829706.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100410000/100408600/100408559/966feace.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/101000000/100410000/100408600/100408559/7d561f10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100410000/100408600/100408559/ad150e08.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)

### The Carlinville Cottage

[](https://www.expedia.ca/Carlinville-Hotels-The-Carlinville-Cottage.h100408559.Hotel-Information)

Carlinville

10/10

Exceptional

(17 reviews)

"Beautiful home, well appointed. Very accommodating host, we have rented this home many times and keep coming back!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Janell M.

CA $307

CA $701 total

includes taxes & fees

Apr 18 - Apr 19

[](https://www.expedia.ca/Carlinville-Hotels-The-Carlinville-Cottage.h100408559.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/43000000/42570000/42565000/42564987/2dbacef1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/43000000/42570000/42565000/42564987/384b3f58.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)

![Terrace/patio](https://images.trvl-media.com/lodging/43000000/42570000/42565000/42564987/853c552f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Home is on the original 1926-1930 Route 66 alignment

[](https://www.expedia.ca/Girard-Hotels-Home-Is-On-The-Original-1926-1930-Route-66.h42564987.Hotel-Information)

Girard

10/10

Exceptional

(101 reviews)

"Very clean, host stayed in contact Really nice place just to get together and visit. The only thing beds were little to firm for our liking and the trains coming through at night!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Marilyn

CA $112

CA $251 total

includes taxes & fees

Apr 8 - Apr 9

[](https://www.expedia.ca/Girard-Hotels-Home-Is-On-The-Original-1926-1930-Route-66.h42564987.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106750000/106748200/106748150/e65f0c1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/107000000/106750000/106748200/106748150/aebe16d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106750000/106748200/106748150/f6f7ac38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/107000000/106750000/106748200/106748150/ea60dc99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy studio located in small town America, Bunker Hill, IL. 

[](https://www.expedia.ca/Bunker-Hill-Hotels-Cozy-Studio-Located-In-Small-Town-America.h106748150.Hotel-Information)

Bunker Hill

10/10

Exceptional

(16 reviews)

"The apartment was very comfortable and cozy. We slept great and it was very nice to have a place to stay in Bunker Hill. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Erica L.

CA $100

CA $173 total

includes taxes & fees

Apr 12 - Apr 13

[](https://www.expedia.ca/Bunker-Hill-Hotels-Cozy-Studio-Located-In-Small-Town-America.h106748150.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/65000000/65000000/64994300/64994277/0c54b2c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player, books, video library](https://images.trvl-media.com/lodging/65000000/65000000/64994300/64994277/db2ed282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/65000000/65000000/64994300/64994277/9c8964e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player, books, video library](https://images.trvl-media.com/lodging/65000000/65000000/64994300/64994277/211d40ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Grand Victorian Carlinville home on Rt. 66\. 

[](https://www.expedia.ca/Carlinville-Hotels-Victorian-Retreat-Close-To-Carlinville-Iconic-Rt-66-Square.h64994277.Hotel-Information)

Carlinville

10/10

Exceptional

(12 reviews)

"Great place to stay"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Adam M.

CA $434

CA $770 total

includes taxes & fees

Apr 11 - Apr 12

[](https://www.expedia.ca/Carlinville-Hotels-Victorian-Retreat-Close-To-Carlinville-Iconic-Rt-66-Square.h64994277.Hotel-Information)

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/21000000/20350000/20348900/20348849/ff0589d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/21000000/20350000/20348900/20348849/de9cb90d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/21000000/20350000/20348900/20348849/382a07f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/21000000/20350000/20348900/20348849/cd635bd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Farmhouse Loft "Greene County's Guesthouse"

[](https://www.expedia.ca/Carrollton-Hotels-The-Farmhouse-Loft-Greene-Countys-Guesthouse.h20348849.Hotel-Information)

Carrollton

9.8/10

Exceptional

(61 reviews)

"Stayed at the Farmhouse Loft for a local wedding. It met all our expectations. Great location on the town square. Will definitely stay there again "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Gregory D.

CA $119

CA $229 total

includes taxes & fees

Apr 9 - Apr 10

[](https://www.expedia.ca/Carrollton-Hotels-The-Farmhouse-Loft-Greene-Countys-Guesthouse.h20348849.Hotel-Information)

![TV, DVD player, video library](https://images.trvl-media.com/lodging/97000000/96870000/96866800/96866707/504bfb9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96870000/96866800/96866707/69c5dbbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/97000000/96870000/96866800/96866707/702d7eb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/97000000/96870000/96866800/96866707/99f46e06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lake House off Route 66

[](https://www.expedia.ca/Lake-Ka-Ho-Hotels-Lake-House-Off-Route-66.h96866707.Hotel-Information)

Mount Olive

9.0/10

Wonderful

(2 reviews)

"We really enjoyed our stay! The Lake House was very clean and met our needs perfectly for our weekend getaway. The property manager was always very responsive! Our dog LOVED the doggy door and the fenced area!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michelle F.

CA $169

CA $338 total

includes taxes & fees

Apr 13 - Apr 14

[](https://www.expedia.ca/Lake-Ka-Ho-Hotels-Lake-House-Off-Route-66.h96866707.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=2026-04-19&endDate=2026-04-20&regionId=553248634983592733&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Chesterfield%2C+Illinois%2C+United+States+of+America&regionId=553248634983592733&latLong=39.255046%2C-90.063163&adults=2&startDate=2026-07-04&d1=2026-07-04&endDate=2026-07-07&d2=2026-07-07&lodging=VACATION_HOME)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Chesterfield%2C+Illinois%2C+United+States+of+America&regionId=553248634983592733&latLong=39.255046%2C-90.063163&adults=2&startDate=2026-07-04&d1=2026-07-04&endDate=2026-07-07&d2=2026-07-07&lodging=APARTMENT)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Chesterfield%2C+Illinois%2C+United+States+of+America&regionId=553248634983592733&latLong=39.255046%2C-90.063163&adults=2&startDate=2026-07-04&d1=2026-07-04&endDate=2026-07-07&d2=2026-07-07&lodging=COTTAGE)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Chesterfield%2C+Illinois%2C+United+States+of+America&regionId=553248634983592733&latLong=39.255046%2C-90.063163&adults=2&startDate=2026-07-04&d1=2026-07-04&endDate=2026-07-07&d2=2026-07-07&lodging=CABIN)

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## Top Chesterfield Hotel Reviews

![Super 8 by Wyndham Staunton](https://images.trvl-media.com/lodging/1000000/70000/62400/62339/e61f32e3_y.jpg)

### Super 8 by Wyndham Staunton

8/10 Good

"Ok as a stopover. Limited continental breakfast."

[](https://expedia.ca/Litchfield-Hotels-Super-8-By-Wyndham-Staunton.h62339.Hotel-Information)

![Hampton Inn by Hilton Litchfield](https://images.trvl-media.com/lodging/2000000/1380000/1374000/1373941/b7297aff_y.jpg)

### Hampton Inn by Hilton Litchfield

4/10 Poor

"Breakfast was good. Staff very friendly. Toilet was loose. Reported it friday AM. Monday AM when we left……still nothing. Could have been a hazard. The hottub/spa inoperable. Never fixed. There’s NO maintenance workers?? Inexcusable. And there’s a Holiday Inn Express right across the street. "

[](https://expedia.ca/Litchfield-Hotels-Hampton-Inn-Litchfield.h1373941.Hotel-Information)

![Cozy studio located in small town America, Bunker Hill, IL. ](https://images.trvl-media.com/lodging/107000000/106750000/106748200/106748150/e65f0c1a_y.jpg)

### Cozy studio located in small town America, Bunker Hill, IL. 

10/10 Excellent

"Host was excellent and responsive to questions. The loft was just as pictured. Very clean, nicely decorated and equipped. Would return and recommend. There’s a couple bar/restaurants a block away with good food/service. Also an ice cream and burger place less than a block. We had a great stay and enjoyed the town. "

[](https://expedia.ca/Bunker-Hill-Hotels-Cozy-Studio-Located-In-Small-Town-America.h106748150.Hotel-Information)

![Super 8 by Wyndham Jerseyville](https://images.trvl-media.com/lodging/1000000/450000/440500/440446/fc493e62_y.jpg)

### Super 8 by Wyndham Jerseyville

10/10 Excellent

"Great experience, friendly staff, clean rooms"

[](https://expedia.ca/Litchfield-Hotels-Super-8-By-Wyndham-Jerseyville.h440446.Hotel-Information)

![Carlin Villa Motel](https://images.trvl-media.com/lodging/12000000/11400000/11392600/11392556/72142117_y.jpg)

### Carlin Villa Motel

8/10 Good

"yes"

[](https://expedia.ca/Litchfield-Hotels-Carlin-Villa-Motel.h11392556.Hotel-Information)

![Light Filled Loft on Town Square](https://images.trvl-media.com/lodging/122000000/121830000/121829800/121829706/3bec06b5_y.jpg)

### Light Filled Loft on Town Square

10/10 Excellent

"Very clean, nice location. Would stay here again. "

[](https://expedia.ca/Carlinville-Hotels-Light-Filled-Loft-On-Town-Square.h121829706.Hotel-Information)

![Cozy little house in town with country view on backdeck.](https://images.trvl-media.com/lodging/74000000/73730000/73724000/73723991/df8d5ceb_y.jpg)

### Cozy little house in town with country view on backdeck.

10/10 Excellent

"This was an amazing find and a tiny little town!The house was very clean, two bedrooms, one bath, big kitchen, really big living/dining room. Outside was adorable, nice big deck, nice patio and even a little outside building made up to be a library with a TV and a fireplace. Very welcoming. There was a grill, an outdoor fireplace, plenty of seating out there as well.The neighborhood is very quiet. I think for a three night stay we might have seen something like four cars.The host left us bottled water, toiletries, washing laundry detergent. It is dog, friendly, and the yard is big for the dogs.Unfortunately, the event that we were there for did not allow us much time to enjoy the backyard or the deck.The town is very small and your options for food and groceries are very limited. The latest restaurant open on Saturday night was only till 8 PM, so just plan ahead on your food.If I come for an event in this area again, I will absolutely rent this house again"

[](https://expedia.ca/Waverly-Hotels-Cozy-Little-House-In-Town-With-Country-View-On-Backdeck.h73723991.Hotel-Information)

![ Memorable Family experiences at The Castle of Palmyra. ](https://images.trvl-media.com/lodging/34000000/33660000/33654500/33654469/739c0b18_y.jpg)

###  Memorable Family experiences at The Castle of Palmyra. 

10/10 Excellent

"First of all, the property is lovely. Debbi is an amazing property manager and extremely helpful! The kitchen is outfitted with everything you could imagine you might need. Lots of places to gather and just be together."

[](https://expedia.ca/Palmyra-Hotels-Memorable-Family-Experiences-At-The-Castle-Of-Palmyra.h33654469.Hotel-Information)

![McClusky Trail Guesthouse
Convenient Access to Jerseyville, Grafton & Alton](https://images.trvl-media.com/lodging/101000000/100960000/100959700/100959686/w504h683x260y0-fa59f152_y.jpg)

### McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton

10/10 Excellent

"We had a wonderful New Year’s Eve stay, everything was clean and as described. The space is very nicely renovated and decorated, highly recommended."

[](https://expedia.ca/Jerseyville-Hotels-McClusky-Trail-GuesthouseConvenient-Access-To-Jerseyville.h100959686.Hotel-Information)

## Find out more about Chesterfield

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . Seeing all the best attractions is bound to make you fall in love with Chesterfield. Who knows, you may even be tempted to extend your vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.   

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- [Vacation Homes in Chesterfield ](https://expedia.ca/Chesterfield-Private-Vacation-Homes.d553248634983592733-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in Chesterfield ](https://expedia.ca/Chesterfield-Apartments.d553248634983592733-aaApartments.Travel-Guide-Accommodation)
- [Motels in Chesterfield ](https://expedia.ca/Chesterfield-Motels.d553248634983592733-aaMotels.Travel-Guide-Accommodation)
- [Cabin Rentals in Chesterfield ](https://expedia.ca/Chesterfield-Cabins.d553248634983592733-aaCabins.Travel-Guide-Accommodation)
- [Castles in Chesterfield ](https://expedia.ca/Chesterfield-Castles.d553248634983592733-aaCastles.Travel-Guide-Accommodation)

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