Holiday Rentals in Chesterfield

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Chesterfield holiday rentals

A patio area with wicker furniture, a striped umbrella, and potted plants.

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, (22 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 €98
includes taxes & fees
16 Nov - 17 Nov
Cozy studio located in small town America, Bunker Hill, IL.
A garden with a bench, various plants, and a house in the background.

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, (114 reviews)
"The house is very well maintained and cared for, the story and its relation to preserving R66 history is wonderful. The hosts were flexible with check-in timing, there is plenty of space for parking and the front porch swing adds a great vibe. Overall, a reasonably priced and comfortable stay! Would definitely recommend."
United States
Cory
The price is €158
includes taxes & fees
19 Nov - 20 Nov
Home is on the original 1926-1930 Route 66 alignment
A spacious room with a large bed, a dining table, and a television.

3. Light Filled Loft on Town Square.

Light Filled Loft on Town Square.
Carlinville
10.0 out of 10, Exceptional, (20 reviews)
"Very clean, nice location. Would stay here again. "
United States
Regina S.
The price is €294
includes taxes & fees
16 Nov - 17 Nov
Light Filled Loft on Town Square.
A room with a wooden wall, a sofa, a round table, a chair, a window with curtains, and a door.

4. Beaver Inn - Cozy 2-bedroom cabin at the entrance of Beaver Dam State Park.

Beaver Inn - Cozy 2-bedroom cabin at the entrance of Beaver Dam State Park.
Plainview
10.0 out of 10, Exceptional, (2 reviews)
"We were able to return to stay a few more days, and the cabin work perfectly for us. The kitchen has everything you need and all of the cookware was cleaned in great condition. The fridge, oven and dishwasher looked like they were brand new and everything worked exactly as expected. The bathroom has a tub which has a large "rain" type of shower head and there is plenty of hot water. The proximity to Beaver Dam is probably one of my favorite things about the house because my family loves to...
United States
Toni G.
The price is €185
includes taxes & fees
14 Dec - 15 Dec
Beaver Inn - Cozy 2-bedroom cabin at the entrance of Beaver Dam State Park.
A bedroom with a wooden headboard, a large bed with white bedding, a bench, and a dresser with a mirror.

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

The Farmhouse Loft "Greene County's Guesthouse"
Carrollton
9.8 out of 10, Exceptional, (64 reviews)
"Very cute place!!!"
United States
Debbie S.
The price is €135
includes taxes & fees
18 Nov - 19 Nov
The Farmhouse Loft "Greene County's Guesthouse"
A laundry room with a front-loading washer and dryer, a bedroom with a bed and a nightstand, and a hallway leading to another room.

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 €209
includes taxes & fees
15 Nov - 16 Nov
McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton
A modern kitchen with white cabinets, stainless steel appliances, and a wooden island with bar stools.

7. The Carlinville Cottage

The Carlinville Cottage
Carlinville
10.0 out of 10, Exceptional, (23 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 €427
includes taxes & fees
16 Nov - 17 Nov
The Carlinville Cottage
A two-story house with a wrap-around porch, a central entrance with a door, and a chimney.

8. 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 €572
includes taxes & fees
14 Nov - 15 Nov
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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Find out more about Chesterfield

Everything you need to know about Chesterfield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterfield holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesterfield holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chesterfield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterfield. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesterfield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesterfield holiday rentals we have selected for you start as low as €75 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesterfield rentals

At Expedia, we put the best Chesterfield holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chesterfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesterfield holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesterfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Cozy little house in town with country view on backdeck.: This holiday home rental outside of Chesterfield offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a selection of books.

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.