Chesterfield Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

    deals illustration

    Better together

    Save up to CA $1,096 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

Ready to book your vacation to Chesterfield?

 

Choose your dates

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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Chesterfield vacation package cost?
You'll find cheap prices on Expedia for your Chesterfield getaway. However, factors like the hotel choice, length of stay and season will determine how much your vacation to Chesterfield costs.
What are the cheapest months to go to Chesterfield?
January, February and July are great times to look for cheap Chesterfield vacation packages. Opting to travel in quieter months means you can generally find better prices on flights and hotels.
How many days is enough for Chesterfield?
With a well-organized schedule, you can easily visit the top Chesterfield attractions in a handful of days. But if you'd like to discover hidden spots or go on day trips, consider booking your Chesterfield vacation for longer.
How to find the best Chesterfield package deals?
Use Expedia's filter tool to find some terrific Chesterfield package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure 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 usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Chesterfield vacation as a package?
You can enjoy significant savings on your next Chesterfield break by booking a personalized vacation package. Check the "Package" heading, then enter your travel dates and destination to browse the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Chesterfield?
If you're considering a spur-of-the-moment Chesterfield getaway, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find sensational deals on your hotels and flights by booking well in advance.
How to plan a trip to Chesterfield?

  1. Pick your travel dates: The things you'd like to do in Chesterfield and your favourite season will help you decide when to get away.
  2. Plan your budget wisely: As well as the cost of your hotel, you should factor in other expenses too. These include transportation, food and flights. Also, set aside some extra funds for unexpected expenses that may arise during your trip to Chesterfield.
  3. Determine how many days away: Start by listing all the sights and activities you'd like to experience in Chesterfield. Then, estimate how long you'll need at each, along with any travel time.
  4. Combine your airfare and accommodations: Once you've nailed down your travel dates and duration, lock in the right Chesterfield vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.