Book Hotels in Chesterfield, IL

Cabins, apartments, houseboats! We offer comfortable & private vacation rentals

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Filter by

Guest rating
Guest rating
Star rating
Payment type
Payment type
Property type
Property type
Neighborhood
Neighborhood
Traveler experience
Traveler experience
Popular locations
Popular locations
Meal plans available
Meal plans available
Property amenities
Property amenities
Accessibility
Accessibility

Top Chesterfield hotels

Memorable Family experiences at The Castle of Palmyra.

Memorable Family experiences at The Castle of Palmyra.

Palmyra IL
This castle features a hot tub and a sauna. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. A ...
"We loved everything about this property. Perfect and plenty of room. We played hide and seek and that was a very long game trying to find everyone."

Reviewed on Aug 25, 2026

Get rates
Opens in a new window Memorable Family experiences at The Castle of Palmyra.
McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton

McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton

Jerseyville IL
The price is $220 total per night from Aug 30 to Aug 31
$220 total
per night
Aug 30 - Aug 31
This vacation home featured laundry facilities and barbecue grills.
"Very comfortable for our family. Well stocked with all the necessities and then some. Thank you!"

Reviewed on Jul 28, 2026

Opens in a new windowMcClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton
Luxurious Otter Pointe

Luxurious Otter Pointe

Girard IL
This cabin featured laundry facilities and barbecue grills.
"Nice"

Reviewed on Aug 20, 2025

Get rates
Opens in a new windowLuxurious Otter Pointe
The Carlinville Cottage

The Carlinville Cottage

Carlinville IL
The price is $504 total per night from Sep 15 to Sep 16
$504 total
per night
Sep 15 - Sep 16
This vacation home features laundry facilities.
"Return visit for us. Well located with ample space for a family and nice yard. Clean well appointed. Highly recommend. We will stay again!"

Reviewed on Jul 5, 2026

Opens in a new windowThe Carlinville Cottage
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 $112 total per night from Sep 13 to Sep 14
$112 total
per night
Sep 13 - Sep 14
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot ...
"This made an excellent home base for my few days of outings and meetings in the Litchfield area. My room was freshened daily and breakfast offerings were more than adequate — I appreciated the real oatmeal and dried fruit and nuts available for toppings. Am not a fan of the interior design style ..."

Reviewed on Aug 26, 2026

Opens in a new windowHampton Inn by Hilton Litchfield
Carlin Villa Motel

Carlin Villa Motel

2.5 out of 5
18891 Rt 4 Old Rt 66 Carlinville IL
Fully refundableReserve now, pay when you stay
The price is $81 total per night from Aug 30 to Aug 31
$81 total
per night
Aug 30 - Aug 31
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a lobby fireplace, and luggage storage are also on offer.
"The rooms are dated but very clean! The rooms are quiet and have everything you need."

Reviewed on Aug 28, 2026

Opens in a new windowCarlin Villa Motel
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 $111 total per night from Sep 27 to Sep 28
$111 total
per night
Sep 27 - Sep 28
This motel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free on-the-go breakfast each morning. A fireplace in the ...
"It needed some updating"

Reviewed on Aug 22, 2026

Opens in a new windowSuper 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 $89 total per night from Sep 28 to Sep 29
$89 total
per night
Sep 28 - Sep 29
This hotel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free continental breakfast each morning. A fireplace in the ...
Opens in a new windowSuper 8 by Wyndham Staunton
Light Filled Loft on Town Square, formerly Karla’s Jewelry bldg.

Light Filled Loft on Town Square, formerly Karla’s Jewelry bldg.

Carlinville IL
The price is $334 total per night from Aug 30 to Aug 31
$334 total
per night
Aug 30 - Aug 31
This apartment features laundry facilities.
Opens in a new windowLight Filled Loft on Town Square, formerly Karla’s Jewelry bldg.
Don't see what you're looking for?
See all available properties in Chesterfield
View all properties
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

What are the top kid-friendly hotels in Chesterfield?
Take some of the stress out of traveling with youngsters by choosing a family-friendly Chesterfield hotel. From useful amenities to innovative services, these properties feature perks that'll make your visit go off without a hitch: Put your bags down at Mid-century Farmhouse- 35 acres- clean & quiet. It comes with a king bed, extra bedding and a talent for making families feel at home. The Shed House- Country Home-Beautiful Sunset View is another great choice. After an exciting day of exploring Chesterfield, return to your comfy room and amenities like a king bed and extra bedding.
Where can I find cheap hotels in Chesterfield?
At Travelocity you'll find really nice hotels in Chesterfield at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Chesterfield rather than in Chesterfield. We may find you even better rates, too.
How do I find the best Chesterfield hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Chesterfield then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Chesterfield?
The cheapest hotel in Chesterfield is $81. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Chesterfield?
There are 28 hotels in Chesterfield on Travelocity.
What are the best hotels in Chesterfield?
Chesterfield has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Chesterfield for you!
When is the best time to visit Chesterfield?
If you want the joy of a fun-filled trip in peak season, visit Chesterfield during June, September and October. If you'd prefer the peace of off-season, book a stay during quieter months, such as November, December and January.
When is the cheapest time to stay in Chesterfield?
Based on historic data is usually the cheapest month to visit Chesterfield. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Chesterfield?
There are multiple hotels in Chesterfield that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Chesterfield. We have plenty of kid-friendly hotels in Chesterfield to choose from on Travelocity!
Why book a hotel in Chesterfield through Travelocity?
Because we have the top hotels in Chesterfield! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Chesterfield on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Chesterfield hotel reviews by fellow wanderers

Carlin Villa Motel

Carlin Villa Motel

5 out of 5
Posted 5 hours ago
Travelocity Verified Review
"The rooms are dated but very clean! The rooms are quiet and have everything you need."
A verified traveler stayed at Carlin Villa Motel
Carlin Villa Motel

Explore More Ways to Travel with Travelocity