Chesterfield Court House Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Chesterfield Court House vacation rentals

A hotel room with a large bed, a window with a view of boats, a lamp, and framed pictures on the wall.

1. MV GiaMaria

MV GiaMaria
3.5 star property
Richmond
9.4 out of 10, Exceptional, (16 reviews)
"So much fun!! Excellent host! Very informative. Loved the privacy and being on the water. The bed was super comfortable and the fireplace (electric) kept us warm and cozy. It was such a unique thing to do and we will be back!"
United States
Jane
The price is CA $301
CA $392 total
includes taxes & fees
Nov 11 - Nov 12
MV GiaMaria
A spacious living area with a high ceiling, a staircase, and a dining area with modern furniture.

2. Game Room + Yard: Updated House in Chester!

Game Room + Yard: Updated House in Chester!
3.0 star property
Chester
The price is CA $169
CA $488 total
includes taxes & fees
Nov 15 - Nov 16
Game Room + Yard: Updated House in Chester!
A boat with a cabin, a small deck area with a ramp, and a docked boat in the background.

3. Cookie B

Cookie B
3.0 star property
Richmond
9.2 out of 10, Wonderful, (10 reviews)
"Was fantastic. Watching the sunrise was so memorable, captain ron was so friendly and stayed in communication well. will visit again. "
United States
Reshelle
The price is CA $309
CA $423 total
includes taxes & fees
Nov 11 - Nov 12
Cookie B
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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Top Chesterfield Court House Hotel Reviews

A modern living room with a sofa, coffee table, and bookshelves.
Country Inn & Suites by Radisson, Richmond I-95 South, VA

Country Inn & Suites by Radisson, Richmond I-95 South, VA

Country Inn & Suites by Radisson, Richmond I-95 South, VA
Bellwood

10/10 Excellent

Nice, newer building. Staff was very friendly and helpful. Room was nice, comfortable, and quiet. Would definitely recommend.
Canada
Mark
Reviewed March 23, 2026
Country Inn & Suites by Radisson, Richmond I-95 South, VA

Find out more about Chesterfield Court House

Everything you need to know about Chesterfield Court House vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterfield Court House vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesterfield Court House vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chesterfield Court House vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterfield Court House. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesterfield Court House vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesterfield Court House vacation rentals we have selected for you start as low as CA $82 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesterfield Court House rentals

At Expedia, we put the best Chesterfield Court House vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chesterfield Court House rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesterfield Court House vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesterfield Court House. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find vacation rentals in Chesterfield Court House?

Yes, we have vacation rentals close to the most popular attractions in Chesterfield Court House, or you can select a more secluded option if you want a relaxing place to stay. Chesterfield Court House is known for its museums.

What are some of the best vacation rentals that Chesterfield Court House has to offer?

Spacious 4-bedroom house in awesome Midlothian with AC: Visitors like this Chesterfield Court House vacation home rental. It offers a fireplace, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

What’s there to see and do in Chesterfield Court House?

Enjoy the area's cultural attractions such as Swift Creek Mill Theatre, or get outdoors into nature at a spot like Maymont Park. While here, Pocahontas State Park and Castlewood are other places worth a visit.

What’s a vacation rental in Chesterfield Court House like?

A vacation rental is a private property you can book for a long or short time in Chesterfield Court House. Vacation rentals feature amenities like WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from public hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for small groups.