Chesterfield Vacations from $432
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The Latest Chesterfield vacation packages
Price found within the past 48 hours. Click for updated prices.
Americas Best Value Inn Bishopville
$432
per person
Oct 28 - Oct 31
found 2 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Florence (FLO)
7.2/10 Good! (98 reviews)
This place was clean with clean sheets, towels, microwave and fridge despite other places that carry the same name that has flaws. This property is very well maintained, and I would highly recommend this place to anyone. The owners are welcoming and friendly if am in the area and need a place to stay I will definitely be staying here.
Deborah
Reviewed on Aug 24, 2026
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Chesterfield Hotel by OYO Hwy 9
321 East Blvd Chesterfield SC
Fully refundableReserve now, pay when you stay
$71 nightly
$77 total
Sep 10 - Sep 11
Total with taxes and fees
4.2/10 (13 reviews)
"For us, it was a not-so-good experience. * We turned on the A/C but it was difficult getting the room to a comfortable temperature. * We had to request another set of sheets. * The mini fridge had mildew along the inside edges of the door. * I couldn’t get any sleep due to the constant itching that ..."
Reviewed on Jun 9, 2026
12 Acre Pond House in Chesterfield - come fish and paddle board! 2BR 2B
Chesterfield SC
$263 nightly
$287 total
Sep 3 - Sep 4
Total with taxes and fees
10/10 Exceptional! (4 reviews)
"Little weekend getaway one hour from home for MX training. Beautiful pond with lots of fish and sassy beavers. Son and husband fished as much as time would allow. Pet-friendly is a plus for us. We plan on returning in the future."
Reviewed on May 17, 2026
Cozy Waterfront Retreat at McMichael Farms
Chesterfield SC
10/10 Exceptional! (12 reviews)
"We absolutely loved our stay here. The house was extremely clean, the beds were super comfortable and the privacy can't be beat. We loved that the ducks would come visit each day, its really cute how they sleep in the cove next to the house each night. We loved fishing from the dock but even more ..."
Reviewed on Nov 13, 2025
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.
Find the Best Chesterfield Vacation Packages
Chesterfield Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
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Frequently asked questions
How much does a Chesterfield vacation package cost?
Offering great value package deals from $432 on Expedia, you'll be surprised at how little a vacation 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'd like to snag a cheap Chesterfield vacation package, consider traveling in December, January and February. You'll generally find better prices on hotels and flights during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Chesterfield?
Generally, a handful of days is enough to go to the major attractions during your Chesterfield vacation. However, if you'd like to have more time to rest or take day tours, consider extending your itinerary.
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 vacation package well in advance.
Is it cheaper to book a Chesterfield vacation as a package?
Expedia vacation 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 personalized Chesterfield vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation 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.
Does Expedia offer Book Now, Pay Later Chesterfield vacation packages?
Secure your dream trip to Chesterfield with Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or hold off until your next paycheck — we've teamed up with online lender Affirm to offer you flexibility and choice. Our vacation packages with payment plans mean you can spread the cost over 3, 6 or 12 months. With no hidden or late payment fees, it's easy to stay on budget and snap up travel deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
