Chesterfield Court House Vacations from $333

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Your Chesterfield Court House Vacation

When a getaway to the city is calling, answer it with a vacation package to Chesterfield Court House. The neighborhood of Downtown Richmond, which is good for nightlife, cafes and festivals, makes a terrific base for your adventures. If your trip to Chesterfield Court House includes a little sightseeing, don't miss much-loved attractions like Pocahontas State Park, Castlewood and Magnolia Grange. No matter your travel plans or the size of your budget, organizing your ultimate tailored Chesterfield Court House vacation is a cinch with Expedia.

The Latest Chesterfield Court House vacation packages

Price found within the past 48 hours. Click for updated prices.
Wingate by Wyndham Richmond Short Pump

Wingate by Wyndham Richmond Short Pump

Short Pump
$333
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Richmond (RIC)
8.4/10 Very Good! (1,707 reviews)
Westgate Historic Williamsburg Resort

Westgate Historic Williamsburg Resort

Midtown
Save 100% on your flight
$745
per person
Dec 27 - Jan 1
found 23 hours ago
Roundtrip non-stop flight included
New Orleans (MSY) to Richmond (RIC)
8.6/10 Excellent! (1,000 reviews)
the staff, the building/facilities itself, and cleanliness were great two things that could use some work though: water took a long time to get warm and didn't stay warm all the time television even when watching regular "live TV" often froze and needed to load/buffer

Reviewed on Oct 2, 2026

The Commonwealth

The Commonwealth

Downtown Richmond
Save 100% on your flight
$528
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Richmond (RIC)
8.8/10 Excellent! (1,407 reviews)
No hot water alas but otherwise a comfortable stay

Reviewed on Oct 13, 2026

Williamsburg Inn, an official Colonial Williamsburg Hotel

Williamsburg Inn, an official Colonial Williamsburg Hotel

Colonial Williamsburg
Save 100% on your flight
$1,281
per person
Dec 27 - Jan 1
found 23 hours ago
Roundtrip non-stop flight included
New Orleans (MSY) to Richmond (RIC)
9.8/10 Exceptional! (411 reviews)
Omni Richmond Hotel

Omni Richmond Hotel

Downtown Richmond
$497
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Richmond (RIC)
9/10 Wonderful! (1,565 reviews)
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Stay near popular Chesterfield Court House attractions

Castlewood

8.0/10 (1 review)
You can find out about the history of Chesterfield Court House with a stop at Castlewood. Stroll along the riverfront or attend a sporting event in the area.
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Magnolia Grange

You can browse the exhibits at Magnolia Grange, a museum with a storied past, during your travels to Chesterfield Court House. Amble around the area's riverfront or attend a sporting event.
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Chesterfield Historical Society of Virginia

You can learn about the history of Chesterfield Court House with a visit to Chesterfield Historical Society of Virginia. Stroll along the riverfront or attend a sporting event in the area.
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What to do in Chesterfield Court House

Historic Trolley Tour

Historic Trolley Tour

$45
per adult
100% of travellers recommend
Historic Trolley Tour
Down in the Shokoe Bottom, the most haunted neighborhood with 350+ years of history and hauntings!

The Haunted History of Richmond tour

$30
per adult
The Haunted History of Richmond tour
Richmond: Guided Hike in James River Park

Richmond: Guided Hike in James River Park

$35
per adult
100% of travellers recommend
Richmond: Guided Hike in James River Park
See all activities in Chesterfield Court House

Chesterfield Court House Hotel Deals

Holiday Inn & Suites Richmond West End

Holiday Inn & Suites Richmond West End

8008 W. Broad St Richmond VA
Fully refundable
$103 nightly
$120 total
Nov 11 - Nov 12
Total with taxes and fees
Holiday Inn & Suites Richmond West End
The Jefferson Hotel

The Jefferson Hotel

101 West Franklin Street Richmond VA
$315 nightly
$366 total
Oct 18 - Oct 19
Total with taxes and fees
The Jefferson Hotel
Drury Plaza Hotel Richmond

Drury Plaza Hotel Richmond

11049 West Broad St Glen Allen VA
Fully refundableReserve now, pay when you stay
$113 nightly
$131 total
Nov 8 - Nov 9
Total with taxes and fees
9.6/10 Exceptional! (2,886 reviews)
"Na"

Reviewed on Oct 12, 2026

Drury Plaza Hotel Richmond
See all 999 properties in Chesterfield Court House
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 Court House Vacation Packages

Chesterfield Court House Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Richmond Intl. Airport (RIC)
Population
3,800
Top Sights
Pocahontas State Park, Pocahontas State Park Museum and Castlewood

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Frequently asked questions

How much does a Chesterfield Court House vacation package cost?
You'll find cheap prices from $333 on Expedia for your Chesterfield Court House break. However, a range of factors like the length of stay, hotel choice and season will determine how much your vacation to Chesterfield Court House costs.
What are the cheapest months to go to Chesterfield Court House?
You can typically find lower rates and greater availability in February, November and December. Take a look at our cheap Chesterfield Court House vacation packages and you could score some excellent off-season deals.
How many days is enough for Chesterfield Court House?
Usually, a handful of days is enough to check out the main attractions during your Chesterfield Court House vacation. However, if you'd like to have more time to unwind or take day tours, think about extending your trip.
Is it worth booking a vacation package to Chesterfield Court House?
It's no wonder a Chesterfield Court House vacation is on the must-do list of many travelers. Major attractions like Castlewood are just the beginning of things to keep you busy here.
How to find the best Chesterfield Court House package deals?
Landing a cheap Chesterfield Court House package deal is a cinch with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget, apply some filters and see what's available. You can customize your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most economical Chesterfield Court House package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Chesterfield Court House vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll generally land a better deal than booking each component individually. And you'll still have the flexibility to create a customized Chesterfield Court House vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Chesterfield Court House?
If you're considering a spontaneous Chesterfield Court House adventure, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can land awesome deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Chesterfield Court House vacation packages?
Set off on your dream escape to Chesterfield Court House with help from our Book Now, Pay Later vacations. No need to save like crazy or wait for the next payday — we've teamed up with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans let you split the cost across 3, 6 or 12 months. With no late payment fees or extra charges, 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.