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Chesterfield Holiday Rentals

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Our top choices for Chesterfield holiday rentals

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, (21 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 NZ$219
includes taxes & fees
26 Oct - 27 Oct
Cozy studio located in small town America, Bunker Hill, IL.

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, (112 reviews)
"Great,quiet,lovely"
United States
Patti H.
The price is NZ$317
includes taxes & fees
15 Nov - 16 Nov
Home is on the original 1926-1930 Route 66 alignment

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 NZ$847
includes taxes & fees
18 Nov - 19 Nov
The Carlinville Cottage

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

The Farmhouse Loft "Greene County's Guesthouse"
Carrollton
9.8 out of 10, Exceptional, (63 reviews)
"Very cute place!!!"
United States
Debbie S.
The price is NZ$289
includes taxes & fees
18 Nov - 19 Nov
The Farmhouse Loft "Greene County's Guesthouse"

5. Light Filled Loft on Town Square.

Light Filled Loft on Town Square.
Carlinville
10.0 out of 10, Exceptional, (18 reviews)
"Very clean, nice location. Would stay here again. "
United States
Regina S.
The price is NZ$564
includes taxes & fees
1 Nov - 2 Nov
Light Filled Loft on Town Square.

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, (29 reviews)
"So nice we already booked for next year!"
United States
Libby W.
The price is NZ$413
includes taxes & fees
22 Oct - 23 Oct
McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton

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 NZ$1,161
includes taxes & fees
26 Oct - 27 Oct
Grand Victorian Carlinville home on Rt. 66.

8. 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 NZ$332
includes taxes & fees
1 Nov - 2 Nov
Cozy 2-bedroom cabin at the entrance of Beaver Dam State Park.
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Chesterfield holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Chesterfield. 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 Chesterfield. 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 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 holiday 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 Chesterfield short-term rentals, that won’t be hard to do.

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 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 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.