Chesterfield Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Top hotels in Chesterfield

Chesterfield Hotel by OYO Hwy 9

Chesterfield Hotel by OYO Hwy 9

2.5 out of 5
321 East Blvd, Chesterfield, SC
Fully refundableReserve now, pay when you stay
The price is S$76 per night from 26 Sept to 27 Sept
S$76
26 Sept - 27 Sept
includes taxes & fees
7.4/10 Good! (3 reviews)
"DO NOT BOOK THIS HOTEL, Staff says they don’t take online reservations, even though it was paid for, had to ask for a refund and during that process staff was shouting to the Expedia employee, felt unsafe during this incident, had to pay for a different hotel in the next town."

Reviewed on 2 Mar, 2025

Chesterfield Hotel by OYO Hwy 9
Bright Converted Schoolhouse in Chesterfield!

Bright Converted Schoolhouse in Chesterfield!

3 out of 5
Chesterfield
Get rates
Bright Converted Schoolhouse in Chesterfield!
Fairfield Inn by Marriott Hartsville

Fairfield Inn by Marriott Hartsville

2.5 out of 5
200 S 4th St, Hartsville, SC
Fully refundableReserve now, pay when you stay
The price is S$148 per night from 7 Sept to 8 Sept
S$148
7 Sept - 8 Sept
includes taxes & fees
8.4/10 Very Good! (652 reviews)
"What did i like All of the above"

Reviewed on 20 Aug, 2025

Fairfield Inn by Marriott Hartsville
See all 79 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?
Offering great value package deals on Expedia, you'll be surprised at how little a holiday to Chesterfield costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Chesterfield?
If you're hoping to score a cheap Chesterfield holiday package, consider visiting in January, February and July. You'll generally find lower rates on accommodation and flights during these months — ideal for budget-conscious travellers.
How many days is enough for Chesterfield?
With a well-planned schedule, you can easily hit the main Chesterfield sights in a few days. But if you prefer to discover hidden spots or go on day tours, consider booking your Chesterfield holiday for longer.
How to find the best Chesterfield package deals?
Use Expedia's handy filters to find some great Chesterfield package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or search for Chesterfield package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your holiday package well in advance.
Is it cheaper to book a Chesterfield holiday as a package?
Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll generally snag a better deal than booking each component separately. And you'll still get the flexibility to create a personalised Chesterfield holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday package to Chesterfield?
If you've got your Chesterfield travel dates confirmed, book early to score some unbeatable deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for setting off on a whim.
How to plan a trip to Chesterfield?

  1. Choose your travel dates: The things you plan to do in Chesterfield and your preferred season will help you decide when to get away.
  2. Plan your budget wisely: In addition to the price of your accommodation, you should consider other expenses. These include flights, transportation and food. Also, put aside some extra funds for unexpected expenses that may come up during your trip to Chesterfield.
  3. Decide your trip length: Think about how much time you'd like to spend discovering Chesterfield. Plan your days so you can get to all the experiences and attractions you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a personalised Chesterfield holiday package.

* 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.