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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 ...
"Such a great experience for the kiddos"

Reviewed on Sep 10, 2026

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Opens in a new window Memorable Family experiences at The Castle of Palmyra.
Light Filled Loft on Town Square, formerly Karla’s Jewelry bldg.

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

Carlinville IL
$284 nightly
The price is $301 total per night from Oct 20 to Oct 21
$301 total
Oct 20 - Oct 21
Total with taxes and fees
This apartment features laundry facilities.
"The place was immaculate. Beautifully refinished loft. Jennifer was also very accommodating and responsive with our check in process,getting us to an event on time!"

Reviewed on Oct 5, 2026

Opens in a new windowLight Filled Loft on Town Square, formerly Karla’s Jewelry bldg.
The Carlinville Cottage

The Carlinville Cottage

Carlinville IL
$490 nightly
The price is $504 total per night from Oct 30 to Oct 31
$504 total
Oct 30 - Oct 31
Total with taxes and fees
This vacation home features laundry facilities.
"It was clean beautiful and updated It had everything you need in case you forgot something."

Reviewed on Oct 1, 2026

Opens in a new windowThe Carlinville Cottage
Luxurious Otter Pointe

Luxurious Otter Pointe

Girard IL
This cabin featured laundry facilities and barbecue grills.
"Great place for large group gatherings, games for young adults and kids, and well stocked kitchen for cooking. Enough beds for many families with children and space so the kids can run. Very peaceful and quiet."

Reviewed on Sep 21, 2026

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Opens in a new windowLuxurious Otter Pointe
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
$106 nightly
The price is $117 total per night from Oct 25 to Oct 26
$117 total
Oct 25 - Oct 26
Total with taxes and fees
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 ...
"Jennifer at check in was great. She totally explained everything. Breakfast was amazing. Bed was so comfortable I want one at home."

Reviewed on Oct 5, 2026

Opens in a new windowHampton Inn by Hilton Litchfield
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
$80 nightly
The price is $89 total per night from Oct 15 to Oct 16
$89 total
Oct 15 - Oct 16
Total with taxes and fees
This hotel 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 ...
"Very clean, comfortable and affordable"

Reviewed on Oct 11, 2026

Opens in a new windowSuper 8 by Wyndham Staunton
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
$73 nightly
The price is $81 total per night from Oct 15 to Oct 16
$81 total
Oct 15 - Oct 16
Total with taxes and fees
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.
"Cute little room on Route 66. The room was very clean. Decor was dated but everything was fairly nice. We had a pond at our window view. Not much road noise or any other noise issues. I loved that there was a REAL key for the door."

Reviewed on Oct 11, 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
$106 nightly
The price is $118 total per night from Oct 25 to Oct 26
$118 total
Oct 25 - Oct 26
Total with taxes and fees
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 ...
Opens in a new windowSuper 8 by Wyndham Jerseyville
Cozy studio located in small town America, Bunker Hill, IL.

Cozy studio located in small town America, Bunker Hill, IL.

Bunker Hill IL
$115 nightly
The price is $122 total per night from Oct 26 to Oct 27
$122 total
Oct 26 - Oct 27
Total with taxes and fees
A garden is available at this apartment.
Opens in a new windowCozy studio located in small town America, Bunker Hill, IL.
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See all available properties in Chesterfield
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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

Home is on the original 1926-1930 Route 66 alignment

Home is on the original 1926-1930 Route 66 alignment

5 out of 5
Posted 2 days ago
Travelocity Verified Review
"We enjoyed our stay very much. Nice neighborhood clean house."
A verified traveler stayed at Home is on the original 1926-1930 Route 66 alignment
Home is on the original 1926-1930 Route 66 alignment

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