Chesterfield Holidays

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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Top hotels in Chesterfield

Hampton Inn by Hilton Litchfield
Hampton Inn by Hilton Litchfield
2.5 out of 5
11 Thunderbird Circle, Litchfield, IL
Fully refundableReserve now, pay when you stay
The price is S$145 per night from 20 Dec to 21 Dec
S$145
includes taxes & fees
20 Dec - 21 Dec
9/10 Wonderful! (547 reviews)
Traveling through
"We were there one night for travel everything was fine"

Reviewed on 10 Nov,2024

Hampton Inn by Hilton Litchfield
Super 8 by Wyndham Jerseyville
Super 8 by Wyndham Jerseyville
2 out of 5
1303 State Highway 109, Jerseyville, IL
Fully refundableReserve now, pay when you stay
The price is S$131 per night from 1 Dec to 2 Dec
S$131
includes taxes & fees
1 Dec - 2 Dec
7.8/10 Good! (282 reviews)
"Only drawback was my next door neighbor was up at 4:00am watching tv loud. Other than that was a great stay. Hotel staff do a great job. I was traveling alone & felt safe the whole time"

Reviewed on 1 Nov,2024

Super 8 by Wyndham Jerseyville
Super 8 by Wyndham Staunton
Super 8 by Wyndham Staunton
2 out of 5
1527 Herman Rd, Staunton, IL
Fully refundableReserve now, pay when you stay
The price is S$112 per night from 26 Nov to 27 Nov
S$112
includes taxes & fees
26 Nov - 27 Nov
8.4/10 Very Good! (688 reviews)
Clean, Comfy, Superb!
"This hotel was quite nice. The receptionist was super friendly. It’s an older hotel and you could tell in some areas but it was exceptionally clean and comfy. Very quiet, ample parking, easy to find. Overall very good."

Reviewed on 14 Nov,2024

Super 8 by Wyndham Staunton
See all 23 properties in Chesterfield
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.

Frequently asked questions

How much does a Chesterfield holiday package cost?
Starting from as low as , you can tailor make your Chesterfield package. Simply combine flights, hotels and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Chesterfield?
One of the easiest ways to save cash (and time) is to bundle your bookings with Expedia. Hotels, rental cars, flights and activities — we’ve got it all. Pick a combination that suits your style and watch your savings grow. Of course, a travel package is never one-size-fits-all. That’s why Expedia offers over 550 airlines and 1,000,000 hotels from all over the world, which lets you customize your Chesterfield getaway.
How far in advance should I book my Chesterfield holiday?
Search Expedia to compare international airfares ASAP. In many cases, you can purchase a ticket up to a year in advance. If you don’t see your preferred air carrier, or you’re booking late, don’t stress. The lowest prices to Chesterfield sometimes emerge within weeks of departure.
What does an Expedia Chesterfield travel package include?
Flights, rental cars and hotels — we have them well covered. With Expedia, you can create your Chesterfield package just the way you want. All you have to do is figure out just what you need. Once you’ve made your booking, you can add extras like experiences and activities. The more you bundle, the greater the savings!
What should I know before booking a Chesterfield travel package?
Locking in all the parts of your trip together is one of the best ways to save. Bundle your flights, car rentals and hotels into a neat package. But you’re not restricted to hotels. Expedia offers all types of properties, including holiday rentals such as beachfront villas and short-term homes. The list is almost endless!
If I'm not able to travel, can I cancel my Chesterfield holiday package?
Because we know life can throw you a few curveballs, the answer is yes. For further information, visit our Customer Service Portal. But generally speaking, if you’ve booked your package in the last 24 hours, you may be able to cancel or change it without penalty. Your hotel, airline or car rental company may impose a fee if you made your booking a while ago.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.