Chesterfield Vacations

Book a Hotel + Flight or Car together to unlock savings

    deals illustration

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    stays illustration

    Find the right fit

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

    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
7.4/10 Good! (3 reviews)
"DO NOT BOOK THIS HOTEL, Staff says they don’t take online reservations, even though it was paid for, had to ask for a refund and during that process staff was shouting to the Expedia employee, felt unsafe during this incident, had to pay for a different hotel in the next town."

Reviewed on Mar 2, 2025

Get rates
Chesterfield Hotel by OYO Hwy 9
Bright Converted Schoolhouse in Chesterfield!
Bright Converted Schoolhouse in Chesterfield!
3 out of 5
Chesterfield
Get rates
Bright Converted Schoolhouse in Chesterfield!
Cozy Waterfront Retreat at McMichael Farms
Cozy Waterfront Retreat at McMichael Farms
2 out of 5
Chesterfield
10/10 Exceptional! (9 reviews)
Peaceful Country Getaway
"This 2-bedroom house in the country was the perfect escape. It’s quiet, relaxing, and beautifully set up for families. The modern amenities made it super comfortable, and the pond out back was a lovely bonus. A great spot to unwind and enjoy some peace and quiet. Can’t wait to come back!"

Reviewed on Apr 16, 2025

Get rates
Cozy Waterfront Retreat at McMichael Farms
See all 80 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 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.