Chesterfield Vacations from $365

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The Latest Chesterfield vacation packages

Price found within the past 48 hours. Click for updated prices.
Affordable Suites Florence

Affordable Suites Florence

2.5 out of 5
Price was $408, price is now $365 per person
$365
per person
Aug 18 - Aug 23
found 19 hours ago
Roundtrip flight included
Philadelphia (PHL) to Florence (FLO)
9.2/10 Wonderful! (182 reviews)
The property was lovely and just what I needed.

Reviewed on Jun 29, 2026

The Inn at the Crossroads

The Inn at the Crossroads

2 out of 5
Price was $796, price is now $652 per person
$652
per person
Aug 8 - Aug 13
found 18 hours ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLO)
9.4/10 Exceptional! (906 reviews)
Super bel hôtel ! Une belle découverte.

Reviewed on Jun 27, 2026

La Quinta Inn & Suites by Wyndham Florence

La Quinta Inn & Suites by Wyndham Florence

3 out of 5
Price was $473, price is now $437 per person
$437
per person
Aug 14 - Aug 17
found 1 day ago
Roundtrip flight included
New York (NYC) to Florence (FLO)
7.8/10 Good! (1,597 reviews)
Very rude night staff. Stains and hair on bed sheets, the floors were greasy, furniture was beat up, chair in room had paint stain. The pictures of the room showed two queen size beds and a sofa bed. Front staff said the pictures are wrong and it’s a room with two queen size beds only. I booked it for 5 people, they expected 3 people to sleep on a queen size beds only. Very disappointed,

Reviewed on Jun 30, 2026

Days Inn by Wyndham Dillon

Days Inn by Wyndham Dillon

2 out of 5
Price was $499, price is now $475 per person
$475
per person
Aug 1 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Florence (FLO)
5.4/10 (896 reviews)
This hotel was the worse I’ve ever been at so bad we couldn’t stay. Smelled like an ash tray roof lights over shower rusted out we walked in looked around and just got back on highway and drove home.

Reviewed on Jun 24, 2026

Red Roof Inn Dillon, SC

Red Roof Inn Dillon, SC

2 out of 5
Price was $482, price is now $482 per person
$482
per person
Aug 1 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Florence (FLO)
6.2/10 (1,003 reviews)
All bad

Reviewed on Jun 29, 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
$79 nightly
The price is $86 total per night from Jul 1 to Jul 2
$86 total
Jul 1 - Jul 2
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

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

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

Chesterfield SC
$260 nightly
The price is $283 total per night from Jul 9 to Jul 10
$283 total
Jul 9 - Jul 10
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

12 Acre Pond House 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

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The Cottage
See all 97 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 $365 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.