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Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

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
Girard
9.8 out of 10, Exceptional, (104 reviews)
"Thank you again for a super easy and wonderful stay!"
United States
Courtney S.
The price is ￥12,907
￥29,239 total
includes taxes & fees
Jul 8 - Jul 9
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.
Bunker Hill
10.0 out of 10, Exceptional, (17 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
Erica L.
The price is ￥11,616
￥20,006 total
includes taxes & fees
Jul 17 - Jul 18
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"
Carrollton
9.8 out of 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
Gregory D.
The price is ￥13,714
￥26,503 total
includes taxes & fees
Jul 21 - Jul 22
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
Jerseyville
10.0 out of 10, Exceptional, (25 reviews)
"In this unique space we found everything we needed if we forgot to bring something, it was supplied with anything you needed. We have booked our next stay before we left."
United States
donald e
The price is ￥17,134
￥35,088 total
includes taxes & fees
Jul 8 - Jul 9
McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton
Fridge, microwave, oven, stovetop

The Carlinville Cottage

The Carlinville Cottage
Carlinville
10.0 out of 10, Exceptional, (20 reviews)
"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 ￥35,495
￥78,823 total
includes taxes & fees
Jul 6 - Jul 7
The Carlinville Cottage
Iron/ironing board, free WiFi, bed sheets

Light Filled Loft on Town Square

Light Filled Loft on Town Square
Carlinville
10.0 out of 10, Exceptional, (13 reviews)
"Very clean, nice location. Would stay here again. "
United States
Regina S.
The price is ￥36,302
￥53,691 total
includes taxes & fees
Jul 6 - Jul 7
Light Filled Loft on Town Square
Exterior

Grand Victorian Carlinville home on Rt. 66.

Grand Victorian Carlinville home on Rt. 66.
Carlinville
10.0 out of 10, Exceptional, (13 reviews)
"Great place to stay"
United States
Adam M.
The price is ￥45,337
￥83,955 total
includes taxes & fees
Jul 20 - Jul 21
Grand Victorian Carlinville home on Rt. 66.
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

Super 8 by Wyndham Jerseyville

Super 8 by Wyndham Jerseyville

8/10 Good
"The rooms were kept clean, and organized and well supplied. Definitely dated in need of updating. staff was helpful and pleasant. Breakfast was good had a good variety of breakfast foods. . Could use some half-and-half for the coffee. Plenty of parking."
Fred 2-night trip
Posted 9 hours ago
Super 8 by Wyndham Jerseyville

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:

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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 Carlinville Public Square, Cheney Mansion, and Jerseyville Historic District. Beaver Dam State Park and American Legion Fairgrounds 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.