Chesterfield Holidays

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Chesterfield Holiday

Our pick of the best Chesterfield Hotel Deals

Bright Converted Schoolhouse in Chesterfield!

Bright Converted Schoolhouse in Chesterfield!

3 out of 5
Chesterfield
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Bright Converted Schoolhouse in Chesterfield!
Chesterfield Hotel by OYO Hwy 9

Chesterfield Hotel by OYO Hwy 9

2.5 out of 5
321 East Blvd, Chesterfield, SC
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

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Chesterfield Hotel by OYO Hwy 9
Cozy Waterfront Retreat at McMichael Farms

Cozy Waterfront Retreat at McMichael Farms

2 out of 5
Chesterfield
10/10 Exceptional! (10 reviews)
"Our stay was wonderful! Everything was beautiful! We enjoyed the ducks and loved having fresh peaches delivered by the owners. Anyone interested in a quiet country setting that just feels good, then this is the place. I highly recommend!"

Reviewed on 11 Jul. 2025

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Cozy Waterfront Retreat at McMichael Farms
See all 77 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.