Chesterfield Court House Vacations from $265

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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.
Club Wyndham Kingsgate

Club Wyndham Kingsgate

3 out of 5
Price was $393, price is now $265 per person
$265
per person
Nov 3 - Nov 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
8.8/10 Excellent! (1,006 reviews)
We had a great experience at Kingsgate, it was awesome to have the extra space, washer and dryer, and kitchen. We arrived earlier then expected and they were able to accommodate us with an early check in so we could start our vacation off right away. Great property and everyone was so friendly.

Reviewed on Aug 26, 2025

Linden Row Inn

Linden Row Inn

3 out of 5
Downtown Richmond
Save 100% on your flight
Price was $445, price is now $298 per person
$298
per person
Nov 3 - Nov 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
9.2/10 Wonderful! (1,147 reviews)
The property was very clean!

Reviewed on Aug 25, 2025

Griffin Hotel, an official Colonial Williamsburg Hotel

Griffin Hotel, an official Colonial Williamsburg Hotel

3 out of 5
Colonial Williamsburg
Save 100% on your flight
Price was $429, price is now $290 per person
$290
per person
Nov 3 - Nov 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
8.8/10 Excellent! (735 reviews)
The property is very large and offers many amenities, including spa and pools and golf. There are many restaurants in the different hotels that are part of the compound. The staff were very helpful and nice

Reviewed on Aug 21, 2025

The Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
Save 100% on your flight
Price was $474, price is now $323 per person
$323
per person
Nov 3 - Nov 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
9/10 Wonderful! (1,011 reviews)
Love the water park for the kids and nice and clean accomidations

Reviewed on Aug 25, 2025

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

3 out of 5
Colonial Williamsburg
Price was $379, price is now $268 per person
$268
per person
Nov 3 - Nov 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
8.8/10 Excellent! (1,542 reviews)
We were moved to the willamslodge it was fantastic! Clean easy walking and lots of things to do. Quiet!

Reviewed on Aug 26, 2025

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Discover the most popular places to visit in Chesterfield Court House

Virginia Commonwealth University

Virginia Commonwealth University

Explore the campus of Virginia Commonwealth University during your stay in Richmond. Stroll along the area's riverfront or experience its great live music.

Virginia Commonwealth University
Game of checkers anyone

University of Richmond

Take a campus tour or just explore the area of University of Richmond, during your trip to Richmond. Attend a sporting event or simply enjoy the charming coffeehouses while you're in the area.

University of Richmond
Richmond

Broad Street

During your trip to Richmond, you can find the perfect gifts to bring home at Broad Street. While you're here, you can savor the top-notch restaurants.

Broad Street

What to do in Chesterfield Court House

Historic Trolley Tour

Historic Trolley Tour

$42
per adult
100% of travellers recommend
Historic Trolley Tour
Richmond: Guided Hike in James River Park

Richmond: Guided Hike in James River Park

$35
per adult
Richmond: Guided Hike in James River Park
See all activities in Chesterfield Court House

Chesterfield Court House Hotel Deals

Graduate by Hilton Richmond

Graduate by Hilton Richmond

4 out of 5
301 West Franklin Street, Richmond, VA
$152 nightly
The price is $177 total per night from Sep 3 to Sep 4
$177 total
Sep 3 - Sep 4
Total with taxes and fees
8.2/10 Very Good! (1,350 reviews)
"Roof top seating area. Able to watch the sun set over the city"

Reviewed on Aug 25, 2025

Graduate by Hilton Richmond
Omni Richmond Hotel

Omni Richmond Hotel

4 out of 5
100 S 12th St, Richmond, VA
Fully refundableReserve now, pay when you stay
$175 nightly
The price is $204 total per night from Sep 7 to Sep 8
$204 total
Sep 7 - Sep 8
Total with taxes and fees
8.8/10 Excellent! (1,169 reviews)
"Was in for a concert , the staff and hotel was just so inviting and friendly I will be back"

Reviewed on Aug 25, 2025

Omni Richmond Hotel
The Jefferson Hotel

The Jefferson Hotel

5 out of 5
101 West Franklin Street, Richmond, VA
Fully refundableReserve now, pay when you stay
$285 nightly
The price is $331 total per night from Sep 1 to Sep 2
$331 total
Sep 1 - Sep 2
Total with taxes and fees
9.8/10 Exceptional! (1,004 reviews)
"Staff very friendly"

Reviewed on Aug 24, 2025

The Jefferson Hotel
See all 886 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.

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Frequently asked questions

How much does a Chesterfield Court House vacation package cost?
You'll find cheap prices from $265 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.