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Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Chesterfield vacation rentals

A spacious room with a large island kitchen, a cozy seating area with a sofa and armchairs, and a bed with a view of the city through arched windows.

1. Light Filled Loft on Town Square, formerly Karla’s Jewelry bldg.

Light Filled Loft on Town Square, formerly Karla’s Jewelry bldg.
Carlinville
10.0 out of 10, Exceptional, (18 reviews)
"Very clean, nice location. Would stay here again. "
United States
Regina S.
The price is ￥35,516
￥52,696 total
includes taxes & fees
Oct 11 - Oct 12
Light Filled Loft on Town Square, formerly Karla’s Jewelry bldg.
A patio area with wicker furniture, a striped umbrella, and potted plants.

2. 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, (20 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 ￥11,365
￥19,573 total
includes taxes & fees
Oct 14 - Oct 15
Cozy studio located in small town America, Bunker Hill, IL.
A modern kitchen with white cabinets, stainless steel appliances, and a wooden island with bar stools.

3. The Carlinville Cottage

The Carlinville Cottage
Carlinville
10.0 out of 10, Exceptional, (22 reviews)
"Beautiful house, our home away from home. We have stayed here many times and we will be back!"
United States
Janell M.
The Carlinville Cottage
A two-story house with a wrap-around porch, a central entrance with a door, and a chimney.

4. 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 ￥47,355
￥89,539 total
includes taxes & fees
Oct 18 - Oct 19
Grand Victorian Carlinville home on Rt. 66.
A bedroom with a wooden headboard, a large bed with white bedding, a bench, and a dresser with a mirror.

5. The Farmhouse Loft "Greene County's Guesthouse"

The Farmhouse Loft "Greene County's Guesthouse"
Carrollton
9.8 out of 10, Exceptional, (63 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 ￥13,417
￥25,930 total
includes taxes & fees
Oct 12 - Oct 13
The Farmhouse Loft "Greene County's Guesthouse"
A garden with a bench, various plants, and a house in the background.

6. 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, (111 reviews)
"absolutely delightful, love it every time, will be back"
United States
connie b.
The price is ￥12,628
￥28,774 total
includes taxes & fees
Oct 14 - Oct 15
Home is on the original 1926-1930 Route 66 alignment
A room with a wooden wall, a sofa, a round table, a chair, a window with curtains, and a door.

7. Cozy 2-bedroom cabin at the entrance of Beaver Dam State Park.

Cozy 2-bedroom cabin at the entrance of Beaver Dam State Park.
Plainview
The price is ￥24,861
￥29,694 total
includes taxes & fees
Oct 8 - Oct 9
Cozy 2-bedroom cabin at the entrance of Beaver Dam State Park.
A laundry room with a front-loading washer and dryer, a bedroom with a bed and a nightstand, and a hallway leading to another room.

8. 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, (29 reviews)
"Nicely appointed space, comfy beds, convenient location."
United States
Mike & JoAnn H.
The price is ￥17,758
￥37,388 total
includes taxes & fees
Oct 7 - Oct 8
McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton
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, formerly Karla’s Jewelry bldg.

Light Filled Loft on Town Square, formerly Karla’s Jewelry bldg.

10/10 Excellent
"The place was immaculate. Beautifully refinished loft. Jennifer was also very accommodating and responsive with our check in process,getting us to an event on time!"
Eric L. 1-night trip
Posted 7 hours ago
Light Filled Loft on Town Square, formerly Karla’s Jewelry bldg.

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
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  • 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?

Cozy little house in town with country view on backdeck.: This vacation home rental outside of Chesterfield offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of books.

What can I see and do in Chesterfield?

While exploring the area, visit the sights like Carlinville Public Square, American Legion Fairgrounds, and Cheney Mansion. Beaver Dam State Park and Westlake Golf Course 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.