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Owner Direct Vacation
Rentals in Chesterfield County
The Best Owner Direct Vacation Rentals in Chesterfield County. Explore thousands of vacation home rentals, large cabins, and villas near Chesterfield County
Find Your Perfect Stay in
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Explore the Best Chesterfield County Vacation Homes
Looking for the perfect place to stay in Chesterfield County? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Chesterfield County character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
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Why Travelers Love Using
Owner Direct to
Find Chesterfield County Vacation Rentals
What makes our vacation homes stand out?
Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Chesterfield County
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Popular Neighborhoods for Chesterfield County Vacation Rentals
What are the best areas to stay in Chesterfield County
Discover the top neighborhoods in Chesterfield County and choose a place that suits your stay.
Monday Sep 21
Chesterfield County, Virginia
Mon
22.7°C
Tue
20.1°C
Wed
17.0°C
Thu
16.3°C
Fri
15.7°C
Sat
16.9°C
Sun
18.2°C
Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Chesterfield County vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near Chesterfield County
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How to Reserve Your Chesterfield County Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
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Chesterfield County Vacation Rental FAQs
What are the top vacation rentals in Chesterfield County?
There are a lot of options in Chesterfield County. If you plan on staying in the Chesterfield County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Chesterfield County:
- Beautiful and Spacious home w/Outdoor Kitchen
- 4-bedroom house in charming Midlothian 20 min to Richmond and Petersburg.
- Charming 4-bedroom house with WiFi, AC in pleasant Chesterfield
- “WaterView" The Pool Pavilion, waterfront property assisted handicap access.
- Luxurious 1-bedroom riverfront Cottage with AC and WiFi in charming Midlothian.
- 3 Family friendly Waterfront homes w/pool, private property with amenities!
- Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.
- Luxurious riverfront Manor with 6 bedrooms and WiFi, AC in fabulous Midlothian
- Qualla Park
- Newly finished basement suite in Midlothian. Very clean and spacious.
How many vacation rentals have private pools in Chesterfield County?
There are 2 vacation rentals with private pools near Chesterfield County. Top-rated homes that have access to a swimming pool include:
Which vacation homes in Chesterfield County are best for families?
If you are looking for a family-friendly vacation home in Chesterfield County, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chesterfield County:
How many vacation rentals are available in Chesterfield County?
Currently, the total number of properties listed in 2026 is over 163 in the Chesterfield County area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Chesterfield County.
