Best Vacation Homes in Chesterfield County
New
House
4 Bedrooms
2 Baths
9 Guests
Fireplace/Heating
Pet Friendly
Air Conditioner
Internet
R5,383/Night
7 Nights - R37,675
Villa
10.0(1 Review)
4 Bedrooms
2 Baths
8 Guests
1453.13 ft²
- Pet Friendly
Kitchen
Parking- Air Conditioner
R3,946/Night
7 Nights - R27,622
Hotel
10.0(2 Reviews)
1 Bath
Child Friendly
Laundry
Guest Services
R3,202/Night
7 Nights - R22,415
New
House
4 Bedrooms
2 Baths
7 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
R3,507/Night
7 Nights - R24,544
House
10.0(1 Review)
4 Bedrooms
4 Baths
8 Guests
3003.13 ft²
- Fireplace/Heating
View- Parking
- Internet
R4,503/Night
7 Nights - R31,519
Cottage
10.0(6 Reviews)
1 Bedroom
1 Bath
4 Guests
500 ft²
- Fireplace/Heating
Balcony/Terrace- Pet Friendly
- Kitchen
R2,555/Night
7 Nights - R17,880
House
10.0(32 Reviews)
4 Bedrooms
3 Baths
8 Guests
3000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
R6,638/Night
7 Nights - R46,468
House
10.0(42 Reviews)
4 Bedrooms
2 Baths
10 Guests
2800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R8,166/Night
7 Nights - R57,160
Chesterfield County Luxury Rentals
House
10.0(6 Reviews)
19 Bedrooms
10 Baths
16 Guests
Private Pool
Spa- Fireplace/Heating
Pool
R56,585/Night
7 Nights - R396,092
House
9.6(4 Reviews)
13 Bedrooms
8 Baths
13 Guests
- Private Pool
- Spa
- Fireplace/Heating
- Pool
R42,875/Night
7 Nights - R300,127
House
9.8(9 Reviews)
8 Bedrooms
6 Baths
18 Guests
7500 ft²
- Private Pool
Hot Tub- Spa
- Fireplace/Heating
R31,397/Night
7 Nights - R219,782
House
10.0(4 Reviews)
6 Bedrooms
5 Baths
12 Guests
7500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R28,740/Night
7 Nights - R201,181
House
10.0(4 Reviews)
8 Bedrooms
4 Baths
20 Guests
- Private Pool
- Fireplace/Heating
- Pool
Ocean View
R25,179/Night
7 Nights - R176,245
House
10.0(8 Reviews)
4 Bedrooms
2 Baths
8 Guests
4496 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
R11,798/Night
7 Nights - R82,588
House
9.8(32 Reviews)
6 Bedrooms
2 Baths
12 Guests
2600 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R10,805/Night
7 Nights - R75,629
House
10.0(5 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R10,723/Night
7 Nights - R75,056
Chesterfield County Pet Friendly Vacation Rentals
House
10.0(18 Reviews)
4 Bedrooms
2 Baths
10 Guests
2000 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R6,200/Night
7 Nights - R43,406
House
1.0(1 Review)
4 Bedrooms
2 Baths
8 Guests
10763.91 ft²
- Fireplace/Heating
- View
- Pet Friendly
- Parking
R3,946/Night
7 Nights - R27,622
Hotel
8.2(1479 Reviews)
1 Bath
Breakfast- Pet Friendly
- Kitchen
- Parking
R2,063/Night
7 Nights - R14,441
House
10.0(14 Reviews)
3 Bedrooms
2 Baths
8 Guests
1350 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
R4,445/Night
7 Nights - R31,110
Villa
1 Bedroom
1 Bath
6 Guests
1302.43 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
R3,949/Night
7 Nights - R27,638
Apartment
10.0(5 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
R4,071/Night
7 Nights - R28,490
House
10.0(2 Reviews)
3 Bedrooms
1 Bath
6 Guests
1300 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R7,145/Night
7 Nights - R50,021
House
10.0(2 Reviews)
2 Bedrooms
2 Baths
5 Guests
1383 ft²
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Kitchen
R3,389/Night
7 Nights - R23,725
Chesterfield County Large Vacation Homes
Boat Rental
9.6(5 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
R5,766/Night
7 Nights - R40,361
House
9.0(8 Reviews)
6 Bedrooms
3 Baths
12 Guests
6500 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R10,296/Night
7 Nights - R72,076
House
4.8(3 Reviews)
4 Bedrooms
3 Baths
16 Guests
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Kitchen
R10,629/Night
7 Nights - R74,401
House
5 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pool
- Kitchen
- Parking
R4,027/Night
7 Nights - R28,195
House
10.0(5 Reviews)
6 Bedrooms
4 Baths
12 Guests
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
R9,298/Night
7 Nights - R65,085
House
5 Bedrooms
3 Baths
12 Guests
4500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R10,027/Night
7 Nights - R70,193
Cottage
4 Bedrooms
4 Baths
16 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
R20,174/Night
7 Nights - R141,222
House
3 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R4,919/Night
7 Nights - R34,434
Why Choose Rent By Owner for your Chesterfield County Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Chesterfield County
When should you plan your Vacation Rentals stay?
Timing your visit to this destination can enhance your experience, so consider the seasonal climate and local events to choose the ideal time for booking your vacation rentals in Chesterfield County, Virginia, USA.
Peak Season Highlights
Late Spring to Early Summer (May - June)
During late spring to early summer, the weather in the region becomes warm and inviting, making it an ideal time for enjoying outdoor activities and exploring local attractions while staying in comfortable vacation rentals.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Fall (September - October)
Autumn offers pleasant temperatures and vibrant foliage, attracting visitors seeking a picturesque setting. This season provides perfect conditions for relaxing stays in the area’s charming vacation rentals.
Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F
Off-Season Highlights
Winter (December - February)
The winter months feature cooler temperatures and fewer tourists, offering quieter and more affordable options for your stay in vacation rentals while exploring the serene beauty of this destination.
Average Temperature Daytime: 40°F to 50°F - Nighttime: 25°F to 35°F
Early Spring (March - April)
Before the peak bloom, early spring presents a peaceful environment with mild temperatures, providing an excellent opportunity to enjoy the region's natural scenery from your vacation rental.
Average Temperature Daytime: 55°F to 65°F - Nighttime: 35°F to 45°F
Weekly Weather Forecast for Chesterfield County
How to Book Your Chesterfield County Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Chesterfield County
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor space with well-maintained gardens or lawns to relax in after exploring the area.
- Take advantage of spacious patios or decks perfect for outdoor dining or entertaining guests.
- Make use of a backyard or outdoor terrace equipped with comfortable seating for enjoying the region’s pleasant weather.
- Benefit from outdoor grilling facilities to prepare delicious meals amid the scenic surroundings.
- Discover outdoor recreational amenities such as swimming pools or hot tubs to unwind during your stay.
- Utilize dedicated areas for outdoor sports or activities, including tennis courts or playsets for families.
- Explore lush landscaping or walking paths that allow you to enjoy the natural beauty here in this destination.
Top Attractions Around Chesterfield County
What attractions are nearby?
Within this area, you can enjoy a variety of activities such as exploring scenic parks, engaging in outdoor sports, or experiencing local cultural attractions, making your stay in Chesterfield County a memorable and enjoyable adventure.
Family Activities
- The Children's Museum of Richmond in Chesterfield County: Engage your family with interactive exhibits designed to inspire curiosity and learning.
- Pocahontas State Park: Discover outdoor adventures like hiking, picnicking, and exploring nature trails suitable for all ages.
- Ceremonial Gardens at Dutch Gap Conservation Area: Enjoy leisurely strolls through beautifully maintained gardens that offer a peaceful retreat for families.
- Swift Creek Mill Theatre: Experience family-friendly performances and cultural events that bring the community here to life.
Adult Activities
- Golfing at nearby courses: Enjoy a relaxing day on the green at some of the region's top golf courses, offering scenic views and challenging play just a short drive from your vacation rental.
- Exploring local parks and nature trails: Discover the natural beauty of the area by walking or biking along well-maintained trails and through lush parks that provide peaceful escapes close to your stay.
- Visiting historical sites and museums: Dive into the region’s rich history by exploring museums and landmarks that highlight Chesterfield County's cultural heritage, all conveniently accessible from your lodging.
- Enjoying outdoor sports and recreational activities: Take advantage of the area's sporting facilities and recreational options, such as tennis courts, fishing spots, or community sports fields near your vacation rental.
Other Places to Stay in Chesterfield County, VA
Moseley
Chesterfield Court House
Ettrick
Chester
Bermuda
Clover Hill
Midlothian
Brandermill
Chesterfield
Woodlake
Woodvale
Chesterfield County Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Attractions: Take time to discover the area's hidden gems and popular spots to fully experience what this destination has to offer.
- Plan Your Activities Ahead: Scheduling visits to nearby parks, museums, or events will help you make the most of your stay here without missing out.
- Choose a Convenient Location: Selecting a vacation rental close to the region's key sites ensures easy access and more leisure time during your visit.
- Embrace the Local Cuisine: Don’t miss out on authentic dining options in the area to enhance your overall experience of this destination.
Transportation Options
- Chesterfield County Transit System: This local transit service offers convenient bus routes, making it easy for you to explore the area without a car while staying in your Chesterfield vacation rental.
- Interstate Highway Access: Major highways such as I-95 and I-295 provide straightforward road connections, ensuring quick access to nearby cities and attractions from your accommodations.
- Amtrak Passenger Rail Service: Although not directly in the area, nearby stations connect you comfortably to regional train networks, ideal for day trips or travel beyond Chesterfield County.
- Rental Car Services: Numerous rental agencies operate in the region, offering flexibility and convenience if you prefer exploring here at your own pace during your stay.
Local Customs Options
- Southern Hospitality: Expect the warm friendliness and welcoming attitude that characterize the area's local customs, making your stay more comfortable and memorable.
: Participating in regional festivals offers a glimpse into the area's rich traditions and community spirit that locals cherish. - Historical Respect: Appreciating the area's history by respecting local landmarks and historic sites enhances your connection with this destination’s cultural heritage.
- Local Cuisine Etiquette: Engaging with the region's culinary traditions often involves embracing shared meals and savoring traditional dishes, enriching your overall experience here.
Frequently Asked Questions About Chesterfield County?
1. 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
- Terre Haute Manor Farmhouse w/Gardens & Deck!
- 4-bedroom house in charming Midlothian 20 min to Richmond and Petersburg.
- Luxe Cottage - South ChesterfieldnStylishly renovated, w/large master suite nnn
- 1-Bedroom Guesthouse with a private entrance, Patio, & Parking
- “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!
- Tranquil Cottage in Virginia Countryside w/Pond!
- Vincent House - Historic Charm & Modern Comfort
2. How many vacation rentals have private pools in Chesterfield County?
There are 6 vacation rentals with private pools near Chesterfield County. Top-rated RBO homes that have access to a swimming pool include:
3. 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:
4. How many Rentbyowner vacation rentals are available in Chesterfield County?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 167 in the Chesterfield County area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Chesterfield County.
5. What is the cancellation policy for vacation rentals in Chesterfield County, Virginia?
Cancellation policies vary by property listing. To understand the specific terms for your booking, please review the cancellation details on the listing or contact the property owner directly.
6. How do I find availability and book a vacation rental in Chesterfield County at the best rates?
Availability and rates are updated regularly online. To secure the best rate, it’s recommended to book early and compare options across listings. You can also reach out to hosts for any special offers or discounts.
7. Are there any house rules or restrictions I should be aware of when staying in a vacation rental here?
Each property has its own house rules and restrictions, which are outlined in the listing. It’s important to read these carefully before booking and contact the owner if you have any questions.
8. What amenities are typically included in vacation rentals around this area?
Amenities vary depending on the property, but many offer essentials like Wi-Fi, parking, and fully equipped kitchens. Check each listing to see what specific amenities are available during your stay.
9. How do I contact the property owner or host if I have questions about my reservation in Chesterfield County?
You can contact the property owner or host directly through the messaging platform provided when you make your reservation. They are available to assist you with any inquiries about your stay.
Chesterfield County Top Rated Vacation Rentals
Hotel
10.0(4 Reviews)
1 Bath
- Private Pool
- Pool
- Child Friendly
Wheelchair Accessible
R2,751/Night
7 Nights - R19,255
Hotel
9.7(23 Reviews)
4 Baths
- Private Pool
- Pool
- Pet Friendly
- Internet
R3,887/Night
7 Nights - R27,213
Apartment
9.6(12 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pool
- Kitchen
- Parking
R2,154/Night
7 Nights - R15,080
Hotel
9.0(393 Reviews)
1 Bath
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
R2,896/Night
7 Nights - R20,270
R2,342/Night
7 Nights - R16,390
Apartment
8.8(6 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Pool
- Kitchen
- Parking
R2,179/Night
7 Nights - R15,260
R2,250/Night
7 Nights - R15,751
Hotel
8.4(593 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
R2,326/Night
7 Nights - R16,275
