Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Chesterfield vacation rentals

Property grounds
Home is on the original 1926-1930 Route 66 alignment

Home is on the original 1926-1930 Route 66 alignment

Home is on the original 1926-1930 Route 66 alignment
Girard
10.0 out of 10, Exceptional, (96)
"The historic house was perfect for our vacation. "
United States
Kelly F.
The price is ￥11,358
￥27,084 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Home is on the original 1926-1930 Route 66 alignment
Terrace/patio
Cozy studio located in small town America, Bunker Hill, IL.

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

Cozy studio located in small town America, Bunker Hill, IL.
Bunker Hill
10.0 out of 10, Exceptional, (14)
"Very comfortable, cozy, and quaint decor. Lovely gardens. Made to feel welcome by host."
United States
Rayma P.
The price is ￥11,358
￥19,561 total
includes taxes & fees
Dec 23 - Dec 24
Cozy studio located in small town America, Bunker Hill, IL.
2 bedrooms, desk, iron/ironing board, travel crib
The Farmhouse Loft "Greene County's Guesthouse"

The Farmhouse Loft "Greene County's Guesthouse"

The Farmhouse Loft "Greene County's Guesthouse"
Carrollton
9.8 out of 10, Exceptional, (61)
"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
Gregory D.
The price is ￥13,409
￥25,914 total
includes taxes & fees
Dec 29 - Dec 30
The Farmhouse Loft "Greene County's Guesthouse"
2 bedrooms, iron/ironing board, travel crib, free WiFi
McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton

McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton

McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton
Jerseyville
10.0 out of 10, Exceptional, (21)
"Nicely appointed space, comfy beds, convenient location."
United States
Mike & JoAnn H.
The price is ￥16,753
￥34,307 total
includes taxes & fees
Dec 30 - Dec 31
McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton
Iron/ironing board, free WiFi, bed sheets
Light Filled Loft on Town Square

Light Filled Loft on Town Square

Light Filled Loft on Town Square
2.0 star property
Carlinville
10.0 out of 10, Exceptional, (1)
"This space is beautiful and everything I hoped it would be for our photo shoot!"
United States
Trista B.
The price is ￥23,978
￥38,452 total
includes taxes & fees
Dec 23 - Dec 24
Light Filled Loft on Town Square
Fridge, microwave, oven, stovetop
The Carlinville Cottage

The Carlinville Cottage

The Carlinville Cottage
Carlinville
10.0 out of 10, Exceptional, (17)
"This was a fantastic stay in a wonderfully clean space! We really enjoyed Carlinville cottage ans would stay again!"
United States
Casey C.
The price is ￥34,705
￥79,075 total
includes taxes & fees
Dec 23 - Dec 24
The Carlinville Cottage
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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Top Chesterfield Hotel Reviews

Light Filled Loft on Town Square

Light Filled Loft on Town Square

10/10 Excellent
"This space is beautiful and everything I hoped it would be for our photo shoot!"
Trista B. 1-night trip
Posted 7 days ago
Light Filled Loft on Town Square

Find out more about Chesterfield

Search for holiday rentals in Chesterfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesterfield using one of the methods below:

  • View our selection of featured holiday rentals in Chesterfield
  • Use the map to find apartments and other holiday homes in the Chesterfield neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chesterfield while they last

Look no further and take a look at our great range of rental properties in Chesterfield!

Frequently asked questions

Can I find vacation rentals in Chesterfield?

Yes, we give you a choice of vacation rentals close to popular attractions in Chesterfield, or you can go with a more remote option if you're looking for a relaxing stay.

What are some of the best vacation rentals in Chesterfield?

Home is on the original 1926-1930 Route 66 alignment: This vacation home rental outside of Chesterfield is located next to a golf course and has a patio, a private yard, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

What can I see and do in Chesterfield?

While exploring the area, visit the sights like Beaver Dam State Park, Carlinville Public Square, and Cheney Mansion. Piney Creek Ravine - State Natural Area and Jersey County Historical Society are a couple of places you'll find in the larger area.

What are vacation rentals like in Chesterfield?

Vacation rentals are privately owned properties you can reserve for a few days or a quick weekend in Chesterfield. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for a family trip.