Chesterfield County Vacation Rentals, Virginia: homes, house rentals & more

Select from 69 houses, 25 apartments, and other vacation rentals to find the perfect place for your stay in Chesterfield County. Vacation homes offer the best amenities for you and your friends, family, or even pets, such as WiFi and a hot tub. At the end of the day, you'll be sure to find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

Popular Chesterfield County destinations on Vrbo

While hiking with my wife in Pocahontas State Park in Virginia we came across this doll left on the trail. I thought it would make for a cool photo.

Find spaces that suit your style

Find the best place to stay - Chesterfield County

Cottage with in steps of swimming pool and poolside lounge

Private Country Retreat with Swimming Pool

Sleeps 6 · 3 bedrooms · 2 bathrooms

The GiaMaria resting in only 4 feet of water and a beautiful oxbow on the James.

A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city

Sleeps 4 · 1 bedroom · 1 bathroom

Private pool and patio grilling area ready for entertaining and relaxing.

Historic Marshall house w/3 King sized beds, 11 total beds & saltwater Pool

Sleeps 16 · 5 bedrooms · 3+ bathrooms

Top rated rentals - Chesterfield County

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Enjoy full kitchens, laundry, pools, yards and more
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Find the perfect vacation rental for your Chesterfield County getaway

Learn about the unique charm of Chesterfield County with a stay in a private vacation home. This city has something for everyone. Many of our vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.

Activities and attractions in and around Chesterfield County

Are you hoping to discover top things to see and do in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Chesterfield County a fun spot to vacation. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

Pocahontas State Park (1.8 mi / 2.8 km)
Iron Bridge Sports Park (6 mi / 9.7 km)
Metro Richmond Zoo (8.8 mi / 14.2 km)
Virginia Motorsports Park (14.5 mi / 23.3 km)
Country Club of Virginia (14.7 mi / 23.6 km)
Richmond Raceway (19.1 mi / 30.8 km)

Exploring the natural landscape of Chesterfield County

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Chesterfield County is a great spot to appreciate mother nature. Here are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city center:

Pocahontas State Park (1.8 mi / 2.8 km)
Richmond National Battlefield Park (13.5 mi / 21.8 km)
Maymont Park (13.5 mi / 21.8 km)
James River (14.3 mi / 23 km)
Pamplin Historical Park (14.8 mi / 23.9 km)
Virginia Capital Trail: Richmond Trailhead (15 mi / 24.2 km)

Traveling to and around Chesterfield County

If you're traveling by train, you can make your way to Petersburg Station.

Frequently asked questions

What is the best area to stay in Chesterfield County when booking a vacation rental?

Among the more popular destinations to book a Vrbo vacation property in Chesterfield County is Chesterfield. Spend your trip here and see some top attractions, such as Pocahontas State Park and Castlewood.

What is the most popular type of vacation rental accommodation in Chesterfield County?

The most sought-after types of vacation rentals in Chesterfield County are houses. Looking for something different? Vrbo has numerous options to match our guests' unique needs, so you'll see vacation properties in loads of shapes and sizes. The ideal home away from home is waiting for you — lock in yours today.

How much does it cost to rent a vacation rental in Chesterfield County?

The average price for a vacation rental in Chesterfield County can vary depending on factors like length of stay, property type and season. Whether you're thinking about a sprawling villa with lots of bedrooms or an apartment that's perfect for two, just add your dates of travel to discover stays with fantastic value.

How much does it cost to rent a beach house in Chesterfield County?

The average price for a vacation home near the beach in Chesterfield County will depend on when you're going and the type and size of property you're searching for. Find prices quickly and easily on Vrbo by entering your destination and travel dates. Then use our filter tool to choose the number of bedrooms and amenities important to you, such as air conditioning, WiFi and a hot tub.

What are popular rental amenities in Chesterfield County?

Free WiFi, a microwave oven and a fridge top the list of most popular rental amenities in Chesterfield County. Whether you're taking to the road by yourself, with your better half or a group of family members, Vrbo will help you find a vacation rental that suits your tastes with all the features you're looking for.

Are there large group vacation rentals in Chesterfield County?

With nine Chesterfield County vacation properties that can host a group of five or more people, you can invite a few extra family members or pals along. Whether you're planning an informal get-together or a special event, Vrbo will help you book a comfy space to match the occasion.

What are the top attractions for families in Chesterfield County?

You'll find lots of cool things to do and see with the family in Chesterfield County, including:

Metro Richmond Zoo
River City Sportsplex
Pocahontas State Park

Can I find two-bedroom vacation rentals in Chesterfield County?

Gather your family and enjoy a relaxing escape in one of the five two-bedroom vacation homes Chesterfield County has to offer.

Are there vacation rentals with WiFi in Chesterfield County?

Pick from 20 vacation rentals with WiFi in Chesterfield County. If you want to disconnect from daily life while on vacation, but still want to be connected to the internet, these properties are just what you need. Narrow your search by applying the WiFi filter on Vrbo.

How old do you have to be to rent a vacation rental in Chesterfield County?

The minimum required age is generally 16, 18 or 21. It can differ across properties on Vrbo, so look at the rules of your chosen Chesterfield County stay before you book.

How long can I rent a vacation rental in Chesterfield County for?

It's down to the Chesterfield County property. To view all available options offering extended stays, just type your dates and number of guests into Vrbo's search page. You can enjoy having the property to yourself, along with home comforts such as air conditioning, a fully-equipped kitchen and a backyard where the kids can burn off energy. Keep an eye out for long-term stays that offer weekly or monthly discounts.