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Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Chesterfield vacation rentals

Terrace/patio

1. 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, (19 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 ￥11,393
￥19,621 total
includes taxes & fees
Aug 22 - Aug 23
Cozy studio located in small town America, Bunker Hill, IL.
Property grounds

2. 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, (109 reviews)
"absolutely delightful, love it every time, will be back"
United States
connie b.
The price is ￥12,658
￥28,843 total
includes taxes & fees
Aug 23 - Aug 24
Home is on the original 1926-1930 Route 66 alignment
Iron/ironing board, WiFi (free), bed sheets

3. 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, (14 reviews)
"Very clean, nice location. Would stay here again. "
United States
Regina S.
The price is ￥35,602
￥52,488 total
includes taxes & fees
Aug 23 - Aug 24
Light Filled Loft on Town Square, formerly Karla’s Jewelry bldg.
2 bedrooms, desk, iron/ironing board, travel crib

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

The Farmhouse Loft "Greene County's Guesthouse"
Carrollton
9.8 out of 10, Exceptional, (62 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 ￥13,450
￥25,993 total
includes taxes & fees
Aug 26 - Aug 27
The Farmhouse Loft "Greene County's Guesthouse"
Coffee/tea maker, fridge, microwave, oven

5. The Carlinville Cottage

The Carlinville Cottage
Carlinville
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful house, our home away from home. We have stayed here many times and we will be back!"
United States
Janell M.
The price is ￥34,811
￥79,316 total
includes taxes & fees
Sep 15 - Sep 16
The Carlinville Cottage
2 bedrooms, iron/ironing board, travel crib, WiFi (free)

6. 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, (27 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 ￥16,804
￥34,746 total
includes taxes & fees
Aug 23 - Aug 24
McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton
Exterior

7. 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 ￥44,463
￥82,672 total
includes taxes & fees
Sep 1 - Sep 2
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

Home is on the original 1926-1930 Route 66 alignment

Home is on the original 1926-1930 Route 66 alignment

10/10 Excellent
"It was nice to have a big house for 5 guests. We got food from the local grocery store and cooked a nice meal at the house. Very relaxing."
Mary Ellen & Drew R. 1-night trip
Posted 1 day ago
Home is on the original 1926-1930 Route 66 alignment

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