Chesterfield Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to SARĀ 5,400 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

Find the Best Chesterfield Vacation Packages

Chesterfield Hotel Deals

The Jefferson Hotel

The Jefferson Hotel

5 out of 5
101 West Franklin Street Richmond VA
Fully refundableReserve now, pay when you stay
The price is SARĀ 1,108 per night from Aug 17 to Aug 18
SARĀ 1,108
SARĀ 1,288 total
17 Aug - 18 Aug
includes taxes & fees
9.8/10 Exceptional! (1,015 reviews)
"Wonderful staff!"

Reviewed on 16 July 2026

The Jefferson Hotel
Omni Richmond Hotel

Omni Richmond Hotel

4 out of 5
100 S 12th St Richmond VA
Fully refundableReserve now, pay when you stay
The price is SARĀ 672 per night from Aug 16 to Aug 17
SARĀ 672
SARĀ 782 total
16 Aug - 17 Aug
includes taxes & fees
Omni Richmond Hotel
Graduate by Hilton Richmond

Graduate by Hilton Richmond

4 out of 5
301 West Franklin Street Richmond VA
Fully refundableReserve now, pay when you stay
The price is SARĀ 584 per night from Aug 16 to Aug 17
SARĀ 584
SARĀ 679 total
16 Aug - 17 Aug
includes taxes & fees
Graduate by Hilton Richmond
See all 1,071 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.

Stay near popular Chesterfield attractions

Pocahontas State Park

8.4/10 (31 reviews)
Virginia's largest state park offers 90+ miles of trails through lush forests and three serene lakes. Explore world-class mountain biking routes or cool off at the seasonal Aquatic Center after a day of adventure.
See properties

Frequently asked questions

How much does a Chesterfield vacation package cost?
You can pick up a vacation package to this destination on Expedia. However, how much your vacation to Chesterfield costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Chesterfield?
Plan your getaway for the off-season and you're likely to find cheap Chesterfield vacation packages. Remember that public holidays and major local events can have an impact on prices, so do a little research before booking.
How to find the best Chesterfield package deals?
Use Expedia's filter tool to help you find some of the best Chesterfield package deals. When you begin 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-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 well in advance.
Is it cheaper to book a Chesterfield vacation as a package?
You can enjoy significant savings on your Chesterfield getaway by booking a customized vacation package. Click on the "Package" heading, then select your destination and travel dates to view some great flight and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Chesterfield?
Enjoy incredible bargains by reserving your flights ahead of time with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Chesterfield escape.
How to plan a trip to Chesterfield?

  1. Choose when to get away: Check your calendar and get your bags packed. Your preferred time of year and the type of activities available will also help you decide when to vacation in Chesterfield.
  2. Set your budget: Consider expenses like flights, food and transportation when working out how much to save for your trip to Chesterfield. Then, select a property that suits your budget, whether that's a wallet-friendly option or a lavish retreat.
  3. Decide how long to go away for: Now that you're up to speed on Chesterfield, you can work out the perfect length of your vacation. Create a rough itinerary and allocate enough time to cover everything you want to do.
  4. Combine your airfare and accommodations: After you've nailed down your trip dates and duration, lock in the ideal Chesterfield vacation package for you.