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Chesterfield Vacation Rentals

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Our top choices for Chesterfield vacation rentals

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 CA $321
CA $473 total
includes taxes & fees
Oct 7 - Oct 8
Light Filled Loft on Town Square, formerly Karla’s Jewelry bldg.

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 CA $103
CA $177 total
includes taxes & fees
Oct 19 - Oct 20
Cozy studio located in small town America, Bunker Hill, IL.

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 price is CA $314
CA $716 total
includes taxes & fees
Oct 30 - Oct 31
The Carlinville Cottage

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 CA $428
CA $805 total
includes taxes & fees
Nov 1 - Nov 2
Grand Victorian Carlinville home on Rt. 66.

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 CA $121
CA $234 total
includes taxes & fees
Oct 15 - Oct 16
The Farmhouse Loft "Greene County's Guesthouse"

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 CA $114
CA $257 total
includes taxes & fees
Nov 1 - Nov 2
Home is on the original 1926-1930 Route 66 alignment

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 CA $224
CA $268 total
includes taxes & fees
Oct 14 - Oct 15
Cozy 2-bedroom cabin at the entrance of Beaver Dam State Park.

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 CA $160
CA $338 total
includes taxes & fees
Oct 8 - Oct 9
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

Find out more about Chesterfield

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chesterfield. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 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.