Chesterfield Vacations from $576

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The Latest Chesterfield vacation packages

Price found within the past 48 hours. Click for updated prices.
Studio 6 Florence , SC

Studio 6 Florence , SC

2.5 out of 5
Price was $596, price is now $576 per person
$576
per person
Jun 19 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Florence (FLO)
3.2/10 (5 reviews)
Holiday Inn Express & Suites Latta by IHG

Holiday Inn Express & Suites Latta by IHG

2.5 out of 5
Price was $846, price is now $810 per person
$810
per person
Jun 19 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Florence (FLO)
9.4/10 Exceptional! (561 reviews)
This was one of the best lodging experiences I've ever had hands down! The biggest plus and amazement is something that doesn't usually happen. I checked out in a hurry to get back on the road. Even after checking the room over before leaving, I neglected to check under the bed covers. I left my Kindle under the covers. At my next destination I called the hotel and told them what stupid mistake I made. Instead of a staff member claiming my Kindle, it was returned to the front desk. The hotel manager offered to ship it to my home address. The day after my return home, UPS showed up in my driveway with the Kindle. This behavior is unheard of these days. This was one of the best things I've experienced in a very long time. Thank You Holiday Inn Express Latta SC!

Reviewed on Mar 22, 2026

Fairfield Inn by Marriott Hartsville

Fairfield Inn by Marriott Hartsville

3 out of 5
Price was $634, price is now $609 per person
$609
per person
Jun 19 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Florence (FLO)
8.6/10 Excellent! (703 reviews)
Easy access to Darlington Speedway

Reviewed on Mar 25, 2026

Holiday Inn Express Hotel & Suites Florence I-95 at Hwy 327 by IHG

Holiday Inn Express Hotel & Suites Florence I-95 at Hwy 327 by IHG

2.5 out of 5
Price was $772, price is now $744 per person
$744
per person
Jun 19 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Florence (FLO)
8.4/10 Very Good! (1,011 reviews)
Nice room. Clean and restful.

Reviewed on Mar 8, 2026

Hyatt Place Florence Downtown

Hyatt Place Florence Downtown

3 out of 5
Price was $810, price is now $781 per person
$781
per person
Jun 19 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Florence (FLO)
9/10 Wonderful! (1,006 reviews)
Great place for our stop on our way to Florida

Reviewed on Mar 27, 2026

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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
$78 nightly
The price is $84 total per night from Mar 30 to Mar 31
$84 total
Mar 30 - Mar 31
Total with taxes and fees
5.4/10 (8 reviews)
They refused Me the room. They said they Only do walk-in. I said I had Booked the room on-line and they said TOO Bad and to leave the motel . They said the booking in-line cost charges a fee and that they will not allow.at to happen

Reviewed on Mar 19, 2026

Chesterfield Hotel by OYO Hwy 9
The Cottage

The Cottage

Chesterfield SC
10/10 Exceptional! (1 review)
Jan and Tim were amazing host and very accommodating. Hopefully see you next year

Reviewed on Mar 16, 2026

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The Cottage
Vintage Villa Guesthouse

Vintage Villa Guesthouse

Chesterfield SC
10/10 Exceptional! (1 review)
Jan is an excellent and welcoming host!
Everything was perfectly clean and organized, she helped us with local information. Five stars and plus

Reviewed on Mar 17, 2020

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Vintage Villa Guesthouse
See all 93 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

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Frequently asked questions

How much does a Chesterfield vacation package cost?
Offering great value package deals from $576 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.