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Chesterfield Vacation 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 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, (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 AED 264
AED 455 total
includes taxes & fees
16 Aug - 17 Aug
Cozy studio located in small town America, Bunker Hill, IL.
Iron/ironing board, WiFi (free), 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, (13 reviews)
"Very clean, nice location. Would stay here again. "
United States
Regina S.
The price is AED 826
AED 1,222 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 AED 294
AED 666 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 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 AED 312
AED 603 total
includes taxes & fees
27 Aug - 28 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 AED 1,032
AED 1,919 total
includes taxes & fees
25 Aug - 26 Aug
Grand Victorian Carlinville home on Rt. 66.
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 AED 390
AED 807 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

Home is on the original 1926-1930 Route 66 alignment

Home is on the original 1926-1930 Route 66 alignment

10/10 Excellent
"We arrive late in the evening all of us were very tired when we got there, but as soon as we stepped into the house, we were so excited on how impressed of the place was that we had explore every room and check out all the features.It worked out very well for us as we had events and family and relatives in Farmersville and surrounding areas.normally, my husband and I stay with relatives, but as two of our adult kids were coming, we didn’t want to impose for people on them. We will definitely keep this place in mind if we return again with extended family."
Karen M. 3-night trip
Posted 2 days ago
Home is on the original 1926-1930 Route 66 alignment

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 American Legion Fairgrounds, Jersey County Historical Society, and Cheney Mansion. Beaver Dam State Park and Carlinville Public Square 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.