Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Chesterfield vacation rentals

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, (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
Erica L.
The price is ￥11,429
￥19,683 total
includes taxes & fees
Jun 1 - Jun 2
Cozy studio located in small town America, Bunker Hill, IL.
Property grounds

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, (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
Marilyn
The price is ￥12,699
￥28,937 total
includes taxes & fees
Jun 1 - Jun 2
Home is on the original 1926-1930 Route 66 alignment
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 ￥13,493
￥26,076 total
includes taxes & fees
Jun 2 - Jun 3
The Farmhouse Loft "Greene County's Guesthouse"
Smart TV

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, (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
Valerie L.
The price is ￥16,858
￥34,018 total
includes taxes & fees
May 20 - May 21
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, (19 reviews)
"Beautiful home, well appointed. Very accommodating host, we have rented this home many times and keep coming back!"
United States
Janell M.
The price is ￥34,923
￥78,730 total
includes taxes & fees
Jun 11 - Jun 12
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, (11 reviews)
"The loft was amazing as well as the views looking out to the town square!"
United States
Gerry G.
The price is ￥35,717
￥52,826 total
includes taxes & fees
May 24 - May 25
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, (12 reviews)
"Great place to stay"
United States
Adam M.
The price is ￥44,606
￥82,939 total
includes taxes & fees
Jun 3 - Jun 4
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

The Carlinville Cottage

The Carlinville Cottage

10/10 Excellent
"Beautiful house, our home away from home. We have stayed here many times and we will be back!"
Janell M. 3-night trip
Posted 21 hours ago
The Carlinville Cottage

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?

McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton: This vacation home rental outside of Chesterfield is located in a rural location and has a selection of games, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What can I see and do in Chesterfield?

While exploring the area, visit the sights like Beaver Dam State Park, Carlinville Public Square, and Piney Creek Ravine - State Natural Area. Jersey County Historical Society and Cheney Mansion 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.