Chesterfield Hotels from S$102

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Our top choices for Chesterfield hotels

Super 8 by Wyndham Jerseyville

Super 8 by Wyndham Jerseyville
2.0 star property
Jerseyville
8.0 out of 10, Very good, (331)
Convenient lodging near Jerseyville Historic District with complimentary Wi-Fi and on-the-go breakfast served daily. Free self-parking makes exploring Jersey County Historical Society and local attractions simple and stress-free.

"Staff was very friendly and room was clean. "
United States
Jeff
The price is S$120
includes taxes & fees
30 Dec - 31 Dec
Super 8 by Wyndham Jerseyville

Hampton Inn by Hilton Litchfield

Hampton Inn by Hilton Litchfield
2.5 star property
Litchfield
9.0 out of 10, Wonderful, (626)
Unwind in this welcoming Litchfield hotel featuring an indoor pool and relaxing hot tub. Start your day with free breakfast before exploring nearby Route 66 Welcome Centre. Enjoy convenient amenities including fitness centre, free WiFi and parking with attentive staff to assist you.

"Was a nice place to stay for a weekend get a way"
United States
Katrina
The price is S$141
includes taxes & fees
28 Dec - 29 Dec
Hampton Inn by Hilton Litchfield

Carlin Villa Motel

Carlin Villa Motel
2.5 star property
Carlinville
8.4 out of 10, Very good, (219)
Conveniently situated near a train station, this motel offers daily housekeeping services and complimentary amenities. Just a short drive from Carlinville Public Square and the local station, guests consistently praise the accommodating staff.

"Our room was phenomenal. So big. Amazing mattress and clean bathroom. It’s an older building and decor, but the room and grounds were clean and well kept. Job well done! "
United States
Mary
The price is S$103
includes taxes & fees
29 Dec - 30 Dec
Carlin Villa Motel

Super 8 by Wyndham Staunton

Super 8 by Wyndham Staunton
2.0 star property
Staunton
8.6 out of 10, Excellent, (765)
Experience tranquility at this Staunton hotel where guests praise the peaceful atmosphere and helpful staff. Just a short drive from The Winery at Shale Lake and offering complimentary parking, breakfast, and WiFi for a comfortable, value-packed stay.

"Both great"
United States
Pam
The price is S$102
includes taxes & fees
12 Jan - 13 Jan, 2026
Super 8 by Wyndham Staunton
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

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Frequently asked questions

What's the best place to stay in Chesterfield?
Located 22.9 mi (36.9 km) from the heart of Chesterfield, Super 8 by Wyndham Staunton is a top choice for your stay, based on our traveller data. Other good choices for your trip to the area are Hampton Inn by Hilton Litchfield and Super 8 by Wyndham Jerseyville. See all available top hotels, or vacation rentals in Chesterfield.
If I need to cancel my hotel reservation in Chesterfield, will I receive a refund?
Yes, the majority of room reservations are fully refundable as long as you cancel before the hotel's cancellation deadline, which is usually within 24-48 hours of your arrival date. If you booked a non-refundable reservation, you might be able to still cancel and get a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Chesterfield.
What's it like staying in Chesterfield?
Travellers to Chesterfield will find plenty to explore and enjoy. There are 26 hotels and other accommodation options in the surrounding area. Find out more about Chesterfield.
What are the top places to visit in Chesterfield?
Places to visit in the wider area include Beaver Dam State Park, Carlinville Public Square and Cheney Mansion. You'll also find Piney Creek Ravine - State Natural Area and Jersey County Historical Society in the area. Take a look at what more there is to see and do in Expedia's Chesterfield guide.
What's the seasonal weather in Chesterfield?
The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 2°C. Average annual precipitation for Chesterfield is 1237 mm.