Title: Chesterfield Vacation Rentals from $124: Search Short-Term Rentals | Expedia.com

[Hotels in Chesterfield](https://expedia.com/Chesterfield-Hotels.d553248634983592733.Travel-Guide-Hotels)[Car Rentals in Chesterfield](https://expedia.com/Car-Rentals-In-Chesterfield.d553248634983592733.Car-Rental-Guide)[Chesterfield Vacation Packages](https://expedia.com/Chesterfield.d553248634983592733.Destination-Travel-Guides)

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## Check prices for these dates

In two weeks

[Apr 17 - Apr 19](https://www.expedia.com/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.com/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.com/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.com/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

![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106750000/106748200/106748150/e65f0c1a.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)

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

![Exterior](https://images.trvl-media.com/lodging/107000000/106750000/106748200/106748150/0d677827.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.com/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.

$117 nightly

$124 total

Apr 4 - Apr 5

Total with taxes and fees

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

![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/w508h683x258y0-cb5da27d.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)

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

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

[](https://www.expedia.com/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.

$203 nightly

$215 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Jerseyville-Hotels-McClusky-Trail-GuesthouseConvenient-Access-To-Jerseyville.h100959686.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/43000000/42570000/42565000/42564987/3ccef999.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)

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

[](https://www.expedia.com/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

$170 nightly

$180 total

Apr 8 - Apr 9

Total with taxes and fees

[](https://www.expedia.com/Girard-Hotels-Home-Is-On-The-Original-1926-1930-Route-66.h42564987.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/21000000/20350000/20348900/20348849/80670dd2.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/cd635bd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.com/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.

$155 nightly

$164 total

Apr 6 - Apr 7

Total with taxes and fees

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

![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)

![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)

### The Carlinville Cottage

[](https://www.expedia.com/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.

$490 nightly

$504 total

Apr 7 - Apr 8

Total with taxes and fees

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

![Property grounds](https://images.trvl-media.com/lodging/97000000/96870000/96866800/96866707/99f46e06.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)

![Interior](https://images.trvl-media.com/lodging/97000000/96870000/96866800/96866707/4e372a45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lake House off Route 66

[](https://www.expedia.com/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.

$224 nightly

$237 total

Apr 13 - Apr 14

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/122000000/121830000/121829800/121829706/91f85310.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)

### Light Filled Loft on Town Square

[](https://www.expedia.com/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.

$315 nightly

$334 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Carlinville-Hotels-Light-Filled-Loft-On-Town-Square.h121829706.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.

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## Find vacation rentals that suit your style

Cabins

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Cottages

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Private vacation homes

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Apartments

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## Top Chesterfield Hotel Reviews

![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.com/Litchfield-Hotels-Hampton-Inn-Litchfield.h1373941.Hotel-Information)

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

### Super 8 by Wyndham Staunton

10/10 Excellent

"Very nice, good breakfast and comfortable beds"

[](https://expedia.com/Litchfield-Hotels-Super-8-By-Wyndham-Staunton.h62339.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.com/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.com/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.com/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.com/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.com/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.com/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.com/Jerseyville-Hotels-McClusky-Trail-GuesthouseConvenient-Access-To-Jerseyville.h100959686.Hotel-Information)

## Find out more about Chesterfield

**Everything you need to know about Chesterfield vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterfield vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesterfield vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Chesterfield vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Chesterfield. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chesterfield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $124 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Chesterfield rentals**

At Expedia, we put the best Chesterfield vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chesterfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesterfield vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesterfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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

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