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- Chesterfield County
- Rentals by Owner
Discover Your Ideal Rental by Owner in Chesterfield County, Virginia for a Comfortable Stay
Discover Your Perfect Chesterfield County Rentals by Owner
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Rentals by Owner
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Luxury Vacation Rentals
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Pet Friendly Vacation Rentals
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Unique Vacation Rentals
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Cabin Rentals
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Cottage Rentals
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Ski Chalet Rentals
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Timeshares
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Hotels with Suites
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Family Vacation Rentals
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Vacation Rentals with Pools
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Oceanfront Vacation Rentals
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Summer Vacation Rentals
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Winter Vacation Rentals
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Corporate Accommodation
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Large Group Vacation Rentals
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Sustainable Travel
Chesterfield County Rentals by Owner
- Air Conditioner
- Pet Friendly
- Security/Safety
- Air Conditioner
- Parking
- View
- Air Conditioner
- Balcony/Terrace
- Security/Safety
- Air Conditioner
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- Pet Friendly
- Air Conditioner
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- TV
- Parking
- Pool
- Accessibility
- Air Conditioner
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- Pet Friendly
- Air Conditioner
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- Balcony/Terrace
- Air Conditioner
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- Pet Friendly
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- View
- Security/Safety
- Air Conditioner
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- Pool
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- Security/Safety
- Sports/Activities
Why Choose Rent By Owner for your Chesterfield County vacation rental?
What makes our Rentals by Owner special?
Best Times to Visit Chesterfield County
When should you plan your Rentals by Owner stay?
Choosing the optimal time to vacation here can enhance your experience, allowing you to enjoy the area's unique charm and seasonal appeal while taking advantage of the best rental options available through Rent By Owner in Chesterfield County, Virginia.
Peak Season Highlights
Spring (March to May)
During spring, the area experiences mild temperatures and vibrant natural scenery, making it an ideal time for outdoor exploration and enjoying the region’s natural beauty.
Fall (September to November)
Autumn brings cooler weather and colorful foliage, providing a picturesque backdrop for your stay and perfect for outdoor activities and scenic drives within the region.
Off-Season Highlights
Summer (June to August)
While summer offers warm weather and longer days, this is also the peak of tourist activity, so accommodations tend to fill quickly, especially if you prefer a lively atmosphere.
Winter (December to February)
In winter, the area experiences colder temperatures and fewer visitors, which can make for a peaceful retreat. This is a good time to find deals on rentals by owner here.
Weekly Weather Forecast for Chesterfield County
How to Book Your Chesterfield County vacation rental
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Chesterfield County
Common Rentals by Owner Amenities
What amenities can you expect?
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 dining with picnic tables or barbecue grills available at your rental.
- Take advantage of private or shared patios and verandas for relaxing outdoors.
- Make use of lush, landscaped yards ideal for outdoor activities or gatherings.
- Benefit from access to community parks or walking trails nearby for outdoor recreation.
- Experience the comfort of swimming pools, either private or communal, during your stay.
- Utilize spacious decks or balconies to enjoy scenic views of the area’s natural beauty.
- Explore outdoor amenities like fire pits or outdoor fireplaces for cozy evenings under the stars.
Top Attractions Around Chesterfield County
What attractions are nearby?
Discover a variety of outdoor activities and local attractions nearby, offering you a memorable experience when staying through Rent By Owner in Chesterfield County, Virginia, USA, with plenty of opportunities to explore the area's natural beauty and cultural sites.
Family Activities
- Chesterfield County Public Library: Engage your family in educational activities and storytimes in this welcoming library, perfect for sparking young imaginations.
- : Enjoy outdoor adventures with picnic areas, playgrounds, and scenic river views that make it an ideal spot for family outings here.
- : Experience a family-friendly shopping trip with diverse stores, dining options, and entertainment to keep everyone entertained in the area.
- : Explore nature trails and observe local wildlife in this peaceful conservation area suited for family hikes and educational nature walks here.
Adult Activities
- Golf at Belwood Country Club: Enjoy an afternoon on the expertly maintained courses, perfect for both beginners and seasoned players seeking a relaxing day in the region.
- Visit the Virginia Museum of Fine Arts at Richmond: Explore diverse art collections and exhibitions that offer cultural enrichment just a short drive from your Chesterfield County rental.
- Explore Pocahontas State Park: Immerse yourself in outdoor activities like hiking, mountain biking, and picnicking within the natural beauty of this expansive park nearby.
- Enjoy wine tasting at local vineyards: Savor regional wines and unwind at nearby vineyards, making the most of the area's thriving wine scene.
Other Places to Stay in Chesterfield County, VA
Chesterfield County Travel Tips
How Can You Make the Most of Your Stay?
- Explore local dining and entertainment options: Take advantage of the area’s vibrant culinary scene to enjoy authentic regional flavors during your stay.
- Plan outdoor activities in nearby parks and nature reserves: The region offers numerous parks and trails perfect for relaxing walks or active adventures, helping you make the most of your visit.
- Utilize nearby amenities and services: Familiarize yourself with local shops, grocery stores, and service providers to ensure a smooth and convenient experience throughout your trip.
- Connect with your rental host for insider tips: Your host can provide valuable recommendations on hidden gems and must-see sights to enhance your stay in this welcoming destination.
Transportation Options
- Chesterfield County Bus Service: This regional bus service offers convenient transportation throughout the area, making it easy to explore without a vehicle.
- Amtrak Rail Lines: Connecting you to nearby cities, the Amtrak station provides reliable rail travel options from here for seamless regional journeys.
- Major Highways and Interstates: Well-maintained highways such as I-95 and US routes facilitate efficient driving experiences for those renting here who prefer their own transport.
- Local Taxi and Rideshare Services: Taxis and rideshare options like Uber and Lyft are readily available within this region, ensuring quick access to your rental accommodation and local attractions.
Local Customs Options
- Southern Hospitality Traditions: Visitors often notice the welcoming attitude and friendly customs that are deeply rooted in the region’s history of Southern hospitality.
- Local Festivals and Events: Participating in or observing regional festivals reflects local customs, emphasizing community spirit and preserving heritage here.
- Georgian Architectural Style: The area's historic buildings showcase a commitment to preserving architectural traditions that date back to colonial times.
- Cuisine and Food Customs: Enjoying traditional Southern dishes and food-sharing practices offers a glimpse into the region’s culinary customs during your stay.
Frequently Asked Questions About Chesterfield County Rentals by Owner
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!
- Entire Home - Close to everything.
- Luxe Cottage - South ChesterfieldnStylishly renovated, w/large master suite nnn
- “WaterView" The Pool Pavilion, waterfront property assisted handicap access.
- 4-bedroom house in charming Midlothian 20 min to Richmond and Petersburg.
- 3 Family friendly Waterfront homes w/pool, private property with amenities!
- Stonewall Manor nCozy 1-bedroom with WiFi and AC on five star horse farm.
- Luxurious riverfront Manor with 6 bedrooms and WiFi, AC in fabulous Midlothian
- 2 Water Front homes w/Pool-Enjoy Resort style!
2. How many Rentbyowner vacation rentals are available in Chesterfield County?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 93 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.
3. What is the cancellation policy for a rental by owner in Chesterfield County, Virginia?
4. How do I contact the property owner before booking a rental by owner in Chesterfield County?
5. Are there any house rules or restrictions when staying in a rental by owner in this area?
6. What amenities are usually included in rentals by owner in Chesterfield County?
7. Is there a minimum stay requirement for rentals by owner here?
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