Chesterfield Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • Better together

    Save up to $1,045 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

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
$57 nightly
The price is $62 total per night from Oct 14 to Oct 15
$62 total
Oct 14 - Oct 15
Total with taxes and fees
6/10 (6 reviews)
Gave away our reservation!
"When, I got there, I was told I didn’t have a reservation-they gave my room to “walk-ins”. After driving 400+ miles, we had to stay at a different hotel."

Reviewed on Sep 29, 2025

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! (11 reviews)
"House was very clean and beautifully furnished. The area is peaceful and quiet. My husband enjoyed fishing on the pond. There are ducks on the property that are fun to watch. Overall very happy with our stay!"

Reviewed on Sep 23, 2025

Get rates
Cozy Waterfront Retreat at McMichael Farms
Bright Converted Schoolhouse in Chesterfield!

Bright Converted Schoolhouse in Chesterfield!

3 out of 5
Chesterfield
Get rates
Bright Converted Schoolhouse in Chesterfield!
See all 83 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.

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 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.