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Chesterfield Holiday Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Chesterfield holiday 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, (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 HK$565
HK$973 total
includes taxes & fees
16 Aug - 17 Aug
Cozy studio located in small town America, Bunker Hill, IL.
Iron/ironing board, free WiFi, bed sheets

2. 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 HK$1,766
HK$2,611 total
includes taxes & fees
16 Aug - 17 Aug
Light Filled Loft on Town Square, formerly Karla’s Jewelry bldg.
Property grounds

3. 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, (108 reviews)
"Thank you again for a super easy and wonderful stay!"
United States
Courtney S.
The price is HK$628
HK$1,422 total
includes taxes & fees
18 Aug - 19 Aug
Home is on the original 1926-1930 Route 66 alignment
2 bedrooms, desk, iron/ironing board, travel cot

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 HK$667
HK$1,289 total
includes taxes & fees
26 Aug - 27 Aug
The Farmhouse Loft "Greene County's Guesthouse"
Exterior

5. 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 HK$2,205
HK$4,100 total
includes taxes & fees
1 Sept - 2 Sept
Grand Victorian Carlinville home on Rt. 66.
2 bedrooms, iron/ironing board, travel cot, free WiFi

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 HK$833
HK$1,723 total
includes taxes & fees
16 Aug - 17 Aug
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

Carlin Villa Motel

Carlin Villa Motel

10/10 Excellent
"Everything was great. It's just a motel and older. BUT, absolutely great customer service. Rooms are super clean and they actually get cleaned daily. Plus the common area where the coffee is at has a cool fireplace. This motel definitely serves it's purpose."
Juan 1-night trip
Posted less than an hour ago
Carlin Villa Motel

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 holiday rentals in Chesterfield?

Yes, there are holiday rentals close to the most popular sights in Chesterfield, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Chesterfield has to offer?

Home is on the original 1926-1930 Route 66 alignment: This holiday home rental outside of Chesterfield is located next to a golf course, and has a patio, a private garden and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What can I see and do in Chesterfield?

While exploring the area, visit the sights like Beaver Dam State Park, Jersey County Historical Society and Cheney Mansion. Carlinville Public Square and American Legion Fairgrounds are a couple of places you'll find in the wider area.

What are holiday rentals like in Chesterfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesterfield. Holiday rentals provide amenities like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from public hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a family trip.