Chesterfield Vacations from $436

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Chesterfield vacation packages

Price found within the past 48 hours. Click for updated prices.
Americas Best Value Inn Bishopville

Americas Best Value Inn Bishopville

2 out of 5
Price was $509, price is now $436 per person
$436
per person
Jun 25 - Jun 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Florence (FLO)
7.2/10 Good! (93 reviews)
The room smelled clean, looked clean and I found no bed bugs. To look at it, we were not sure about our choice. But the wife and I were very pleased. If in the area, we will definitely stay there again.

Reviewed on Oct 27, 2025

Affordable Suites Florence

Affordable Suites Florence

2.5 out of 5
Price was $572, price is now $502 per person
$502
per person
Jul 2 - Jul 7
found 6 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Florence (FLO)
9.2/10 Wonderful! (166 reviews)
This place was great, but they should have blankets available maybe in the closet.

Reviewed on May 11, 2026

Red Roof Inn Bishopville

Red Roof Inn Bishopville

2 out of 5
Price was $459, price is now $459 per person
$459
per person
Jun 25 - Jun 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Florence (FLO)
6.4/10 (144 reviews)
Good for a day or 2 but not a long time

Reviewed on Mar 24, 2026

Don't see what you're looking for?
See all available trips from Columbus to Chesterfield
View all trips

Chesterfield Hotel Deals

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
$76 nightly
The price is $82 total per night from May 24 to May 25
$82 total
May 24 - May 25
Total with taxes and fees
5/10 (9 reviews)
Worst hotel I've ever stayed at. I think this may be the first review I've ever done of a hotel but just need to warn folks. The owner lives on site and has zero customer service skills. When I checked in he said, he needed to put toilet paper and towels in the room. Then he told me he was going ...

Reviewed on May 3, 2026

Chesterfield Hotel by OYO Hwy 9
12 Acre Pond House Cottage in Chesterfield - come fish and paddle board! 2BR/2B

12 Acre Pond House Cottage in Chesterfield - come fish and paddle board! 2BR/2B

Chesterfield SC
$237 nightly
The price is $258 total per night from May 21 to May 22
$258 total
May 21 - May 22
Total with taxes and fees
10/10 Exceptional! (3 reviews)
We loved staying here! Ingrid, Buddy and I have stayed at hundreds of places over the years, and this is easily in the top three. Our gracious host Margaret was ready to respond quickly with any questions we had. We loved the floorplan. Ingrid cooked enchiladas in the kitchen. The beds were extremely ...

Reviewed on May 6, 2026

12 Acre Pond House Cottage in Chesterfield - come fish and paddle board! 2BR/2B
The Cottage

The Cottage

Chesterfield SC
10/10 Exceptional! (2 reviews)
Clean, quiet, and peaceful rural setting. We enjoyed morning coffee on the porch. Ideal location for us visiting our daughter and grandson. We hope to return often.

Reviewed on May 11, 2026

Get rates
The Cottage
See all 92 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.

Find the Best Chesterfield Vacation Packages

Chesterfield Essential Information

Language
English
Currency
U.S dollars

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Chesterfield vacation package cost?
Offering great value package deals from $436 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.