1. USA
  2. South Carolina
  3. Chesterfield
  4. Rentals by Owner

Discover Your Perfect Chesterfield Rentals by Owner

Chesterfield Rentals by Owner

More Top-Rated Rentals by Owner in Chesterfield Area

Why Choose Rent By Owner for your Chesterfield vacation rental?

What makes our Rentals by Owner special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Chesterfield

When should you plan your Rentals by Owner stay?

Understanding the best time to visit can enhance your experience when booking a rental by owner in Chesterfield, South Carolina, USA, allowing you to enjoy the area’s local charm at its most inviting throughout the year.

Peak Season Highlights

spring
Spring (March to May)

During this period, the area experiences pleasant weather, making it an ideal time for exploring and outdoor activities. Booking your rental here ensures a comfortable stay amidst blooming scenery.

Average Temperature Daytime: 70°F - 80°F - Nighttime: 50°F - 60°F
autumn
Fall (September to November)

The region offers mild temperatures and vibrant autumn colors, perfect for sightseeing and enjoying the local atmosphere. Secure your rental early for an authentic experience during this scenic season.

Average Temperature Daytime: 65°F - 75°F - Nighttime: 45°F - 55°F

Off-Season Highlights

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Summer (June to August)

While the summer months bring warmer weather, this is also a quieter time for lodging, offering more affordable rental options and less crowded attractions here.

Average Temperature Daytime: 85°F - 95°F - Nighttime: 65°F - 75°F
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Winter (December to February)

The cooler season sees fewer visitors, providing a cozy retreat with potential discounts on rentals. It’s a peaceful time to relax and enjoy the tranquility of the area.

Average Temperature Daytime: 50°F - 60°F - Nighttime: 30°F - 40°F

Weekly Weather Forecast for Chesterfield

How to Book Your Chesterfield vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. 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

More Top-Rated Rentals by Owner in Chesterfield Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner 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 outdoor spaces with access to a private or shared backyard perfect for relaxing or entertaining.
  • Take advantage of a well-maintained patio or deck area ideal for dining outdoors or unwinding after a day of exploring.
  • Benefit from scenic views and tranquil surroundings, enhancing your overall vacation experience in this inviting destination.
  • Utilize outdoor grilling facilities to prepare delicious meals while enjoying the fresh air.
  • Explore nearby walking or biking trails that showcase the natural beauty of the region.
  • Make use of a swimming pool or hot tub, perfect for unwinding during the warmer months or cooler evenings.
  • Experience outdoor recreational amenities such as a fire pit or hammock, offering additional ways to relax and enjoy your stay here.

Top Attractions Around Chesterfield

What attractions are nearby?

In this welcoming destination, you can enjoy a variety of outdoor activities, explore charming local attractions, and experience the region’s natural beauty—all easily accessible from your rental by owner in Chesterfield.

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Family Activities

  • Chesterfield County Museum: You can explore local history and enjoy interactive exhibits that are perfect for engaging young minds during your stay in the area.
  • Riverside Park: This scenic park offers family-friendly amenities such as playgrounds, picnic areas, and walking trails, making it an ideal spot for outdoor fun in the region.
  • Lake Monticello: Relax and unwind by the water with fishing, boating, or simply enjoying a leisurely day, all within easy reach of your vacation rental in this destination.
  • Wildlife Watching in Nature Reserves: The surrounding natural reserves provide fantastic opportunities to observe local wildlife and connect with nature here in the region.
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Adult Activities

  • Golfing at Chesterfield Golf Club: Test your skills on the scenic courses designed to provide a relaxing yet engaging experience here in the region.
  • Exploring local art galleries: Discover the vibrant art scene and unique southern craftsmanship that showcase the area's creative spirit.
  • Enjoying outdoor recreation at nearby parks: Take advantage of hiking, picnicking, or simply unwinding amidst the natural beauty surrounding this destination.
  • Attending cultural events and festivals: Immerse yourself in authentic regional traditions and lively gatherings that highlight the community's warmth and heritage.

Chesterfield Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Events and Festivals: Check out community events in the area to immerse yourself in local culture and enhance your stay in Chesterfield.
  • Choose a Rental Close to Nature: Opt for accommodations near parks or outdoor attractions to enjoy the natural beauty that this region offers.
  • Plan Your Transportation: Arrange reliable transportation options within the area to easily access key spots and make the most of your visit.
  • Communicate Clearly with Hosts: Use detailed inquiries to ensure your rental meets your needs, allowing for a smoother experience here in South Carolina's charming destination.

Transportation Options

  • Chesterfield County Public Transit: This reliable bus service offers convenient transportation throughout the area, making it easy to explore your rental and nearby attractions.
  • Private Taxi Services: Local taxi companies provide on-demand rides that ensure quick and comfortable travel around the region from your Chesterfield rental.
  • Rental Car Agencies: Major rental agencies located near Chesterfield enable you to explore the surrounding area with flexibility and ease during your stay.
  • Bike Rentals and Pedestrian Paths: For a more leisurely experience, bike rentals and designated trails allow you to enjoy the scenic views of this destination at your own pace.

Local Customs Options

  • Southern Hospitality:** You can expect a warm welcome and courteous interactions, reflecting the region's renowned friendliness toward visitors seeking vacation rentals in Chesterfield.
  • Community Festivals:** Local festivals celebrate regional traditions and bring residents and travelers together, creating memorable experiences during your stay in this part of South Carolina.
  • Religious Observances:** Respect for religious practices is common here, with many community events centered around churches that hold significance for locals and visitors alike.
  • Local Cuisine Etiquette:** When enjoying regional dishes, it’s customary to appreciate the farm-fresh ingredients and hospitality that define this area's culinary culture.

Frequently Asked Questions About Chesterfield Rentals by Owner

1. What are the top vacation rentals in Chesterfield?

There are a lot of options in Chesterfield. If you plan on staying in the Chesterfield 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:

2. How many Rentbyowner vacation rentals are available in Chesterfield?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 21 in the Chesterfield 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. 

3. What is the cancellation policy for rental properties booked through Rent By Owner in Chesterfield?

Cancellation policies vary by listing, so it’s important to review the specific terms on each rental’s page or contact the owner directly to understand the details related to cancellations and potential refunds.

4. How do I communicate with the property owner before booking my stay in Chesterfield?

You can use the messaging feature on the rental listing page to ask questions or clarify details with the owner, ensuring you have all necessary information before confirming your reservation.

5. Are there any additional fees or deposits required when booking a rental by owner in this region?

Additional fees or security deposits are often listed during the booking process or within the property details. It’s advisable to review these details carefully or reach out to the owner for clarification before finalizing your reservation.

6. What amenities are typically included in rentals available in Chesterfield?

Amenities vary by property but generally include essentials such as Wi-Fi, parking, and kitchen facilities. For specific features, check the listing details or contact the owner directly to ensure the property meets your needs.

7. How do I confirm the availability of a rental property in this destination?

Availability is shown on each property’s calendar during the booking process. If you need further confirmation, contacting the owner directly can help verify dates and secure your reservation.

More Rentals You May Like Near Chesterfield

More Top-Rated Rentals by Owner in Chesterfield Area