Best Vacation Homes in Chesterfield
New
House
4 Bedrooms
2 Baths
9 Guests
Fireplace/Heating
Pet Friendly
Air Conditioner
Internet
AU $455/Night
7 Nights - AU $3,183
Villa
10.0(1 Review)
4 Bedrooms
2 Baths
8 Guests
1453.13 ft²
- Pet Friendly
Kitchen
Parking- Air Conditioner
AU $333/Night
7 Nights - AU $2,333
Hotel
9.0(638 Reviews)
1 Bath
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
AU $180/Night
7 Nights - AU $1,263
House
10.0(9 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
Balcony/Terrace- Kitchen
- Parking
AU $161/Night
7 Nights - AU $1,129
House
1.0(1 Review)
4 Bedrooms
2 Baths
8 Guests
10763.91 ft²
- Fireplace/Heating
View- Pet Friendly
- Parking
AU $333/Night
7 Nights - AU $2,333
Apartment
10.0(5 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $201/Night
7 Nights - AU $1,404
House
10.0(4 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
AU $261/Night
7 Nights - AU $1,828
House
10.0(3 Reviews)
3 Bedrooms
1 Bath
6 Guests
1300 ft²
Hot Tub- Fireplace/Heating
Ocean View- Balcony/Terrace
AU $332/Night
7 Nights - AU $2,324
Chesterfield Luxury Rentals
House
9.8(9 Reviews)
4 Bedrooms
2 Baths
7 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
AU $504/Night
7 Nights - AU $3,528
House
3 Bedrooms
2 Baths
8 Guests
1571.53 ft²
- Fireplace/Heating
- Balcony/Terrace
- Parking
- Air Conditioner
AU $386/Night
7 Nights - AU $2,703
House
9.6(9 Reviews)
3 Bedrooms
2 Baths
8 Guests
1561 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
AU $364/Night
7 Nights - AU $2,550
House
5 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
Pool- Kitchen
- Parking
AU $340/Night
7 Nights - AU $2,382
Villa
1 Bedroom
1 Bath
6 Guests
1302.43 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
AU $334/Night
7 Nights - AU $2,335
House
6.0(2 Reviews)
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
Child Friendly
AU $326/Night
7 Nights - AU $2,285
Hotel
8.9(188 Reviews)
1 Bath
150.69 ft²
- Fireplace/Heating
- Parking
- Air Conditioner
- Internet
AU $242/Night
7 Nights - AU $1,692
Hotel
7.7(147 Reviews)
7 Baths
349.06 ft²
- Fireplace/Heating
Breakfast- Parking
- Air Conditioner
AU $238/Night
7 Nights - AU $1,668
Chesterfield Pet Friendly Vacation Rentals
House
3 Bedrooms
2 Baths
5 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
AU $222/Night
7 Nights - AU $1,552
House
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
AU $111/Night
7 Nights - AU $777
House
10.0(5 Reviews)
6 Bedrooms
4 Baths
12 Guests
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
AU $785/Night
7 Nights - AU $5,498
House
5.0(3 Reviews)
4 Bedrooms
2 Baths
8 Guests
- View
- Pet Friendly
- Kitchen
- Air Conditioner
AU $422/Night
7 Nights - AU $2,953
House
4.4(5 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Pet Friendly
- Air Conditioner
- Child Friendly
Laundry
AU $422/Night
7 Nights - AU $2,953
House
2.0(2 Reviews)
2 Bedrooms
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
AU $131/Night
7 Nights - AU $914
House
3 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $416/Night
7 Nights - AU $2,909
House
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $203/Night
7 Nights - AU $1,425
Chesterfield Top Rated Vacation Rentals
Apartment
10.0(3 Reviews)
1 Bedroom
1 Bath
2 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
AU $238/Night
7 Nights - AU $1,668
Apartment
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
AU $296/Night
7 Nights - AU $2,072
Apartment
3 Bedrooms
2 Baths
6 Guests
1377 ft²
- Pool
- Pet Friendly
- Kitchen
- Air Conditioner
AU $187/Night
7 Nights - AU $1,311
Apartment
1 Bedroom
1 Bath
2 Guests
839 ft²
- Pool
- Pet Friendly
- Kitchen
- Air Conditioner
AU $137/Night
7 Nights - AU $961
Why Choose Rent By Owner for your Chesterfield 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.
Popular Areas for Chesterfield Vacation Rentals
Where are the best neighborhoods to stay in Chesterfield?
When exploring Chesterfield, Virginia, selecting the right neighborhood to stay in can greatly enhance your visit. Whether you're seeking a peaceful residential area or a lively community with easy access to local amenities, each neighborhood offers its own unique charm. As you browse through available vacation rentals, consider regions that align with your interests and travel plans to ensure a comfortable and memorable stay in this welcoming part of Virginia. With thoughtfully chosen accommodations in Chesterfield, you'll enjoy a convenient base to experience all that the area has to offer.
North Chesterfield
In this part of the region, you can enjoy convenient access to local amenities and a welcoming community atmosphere that makes your stay memorable. The area offers a variety of vacation rentals nestled in a peaceful setting, perfect for travelers seeking comfort and ease.
View 195+ Rentals in North ChesterfieldHampton Park
Here, you have the opportunity to experience a charming neighborhood with easy access to outdoor spaces and local conveniences. The vacation rentals available provide a comfortable base for exploring the area's scenic surroundings and vibrant community life.
View 51+ Rentals in Hampton ParkBest Times to Visit Chesterfield
When should you plan your Vacation Rentals stay?
Choosing the right time to vacation here can enhance your experience, as the region offers distinct seasonal charms that cater to a variety of interests and preferences.
Peak Season Highlights
Spring (March to May)
During the spring months, the area experiences mild temperatures and blooming landscapes, making it an ideal time for outdoor activities and exploring local attractions.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
Fall (September to November)
The fall season features cooler weather and vibrant foliage, providing a picturesque setting for sightseeing and enjoying the region's natural beauty.
Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F
Off-Season Highlights
Summer (June to August)
While summer brings warm weather perfect for outdoor recreation, this period is also quieter in terms of travel demand, offering peaceful stays in the area’s vacation rentals.
Average Temperature Daytime: 80°F to 90°F - Nighttime: 60°F to 70°F
Winter (December to February)
The winter months tend to be less busy with cooler temperatures, making it a cozy time to enjoy indoor amenities and explore fewer crowds at popular spots.
Average Temperature Daytime: 40°F to 50°F - Nighttime: 25°F to 35°F
Weekly Weather Forecast for Chesterfield
How to Book Your Chesterfield 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
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 outdoor dining areas for relaxing meals under the open sky.
- Take advantage of spacious gardens or yards ideal for outdoor activities and gatherings.
- Make use of private patios or decks to unwind while enjoying scenic views of the surrounding area.
- Benefit from access to community pools or lakes, perfect for swimming and water-based recreation.
- Use outdoor grills or barbecue facilities to host cookouts with family and friends.
- Explore nearby walking trails or nature paths that showcase the region’s natural beauty.
- Utilize ample parking spaces with some properties offering covered or shaded parking for convenience.
Top Attractions Around Chesterfield
What attractions are nearby?
In this area, you can enjoy a variety of outdoor activities, cultural experiences, and local attractions just moments from your vacation rentals in Chesterfield, providing a perfect blend of relaxation and exploration during your stay.
Family Activities
- Chesterfield County Family Fun Center: Enjoy a day of arcade games, bowling, and mini-golf perfect for family bonding in this popular destination.
- The Children's Museum of Richmond at the Science Museum of Virginia: Engage young minds with interactive exhibits and educational activities just a short drive away in this engaging museum.
- : Explore hiking trails, enjoy picnicking, or take part in outdoor adventures suitable for all ages within this expansive regional park.
- Historic Courthouse and Old Town Chesterfield: Discover the area's rich history through walking tours and historic sites that provide a glimpse into its past charm.
Adult Activities
- Golf at The CC of Virginia: Enjoy a round of golf on this premier course, offering scenic views and challenging gameplay just minutes from your vacation rental.
- Visit the Snag Golf Course: Perfect for golf enthusiasts seeking a relaxed and picturesque setting to practice their swing in the region.
- Explore local parks and outdoor spaces: Discover tranquil spots like Pocahontas State Park, where you can hike, bike, or simply unwind amidst nature’s beauty.
- Attend community events and festivals: Immerse yourself in the area's vibrant culture through seasonal festivals, farmers markets, and outdoor concerts easily accessible from your stay.
Other Places to Stay in Chesterfield, VA
Chesterfield County
Chesterfield Court House
Chesterfield Historical Society of Virginia
Magnolia Grange
Castlewood
Pocahontas State Park Museum
Pocahontas State Park
Hampton Park
Oasis Sports Park
Chesterfield Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Local Events: Check the region’s event calendar to align your stay with local festivals or community gatherings that showcase the area’s unique culture.
- Explore Nearby Attractions: Take advantage of the proximity to natural and cultural sites, making sure your vacation rentals are conveniently located to explore the best of the destination.
- Prioritize Comfort and Convenience: Choose well-reviewed accommodations that offer essential amenities to enhance your relaxation and make your trip hassle-free.
- Sample Regional Cuisine: Use your stay as an opportunity to indulge in local dining experiences, discovering flavors that truly represent this part of the country.
Transportation Options
- Chesterfield County Transit: This reliable public transportation option offers convenient bus routes throughout the area, making it easy to explore your surroundings without a car.
- Rental Car Services: Numerous rental agencies operate nearby, providing flexible transportation for exploring Chesterfield and its scenic surroundings at your own pace.
- Taxi and Rideshare Services: Available throughout the region, these services offer quick, comfortable rides when you prefer door-to-door transportation during your stay.
- Regional Airport Access: Richmond International Airport is the closest major airport, connecting travelers to Chesterfield via various shuttle, taxi, and rental options for seamless arrivals and departures.
Local Customs Options
- Southern Hospitality: Experience the warm and welcoming spirit that is characteristic of this region’s friendly community and local gatherings.
- Historic Ceremony Practices: Respect the area’s rich history by observing traditional ceremonies and events during your stay.
- Local Food Customs: Savor regional specialties that highlight the culinary heritage unique to this destination in Virginia.
- Community Engagement: Participate in neighborhood events and support local artisans to embrace the area's close-knit culture.
Frequently Asked Questions About Chesterfield?
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:
- 1-Bedroom Guesthouse with a private entrance, Patio, & Parking
- Stonewall Manor nCozy 1-bedroom with WiFi and AC on five star horse farm.
- Newly finished basement suite in Midlothian. Very clean and spacious.
- Qualla Park
- A Southside Retreat the whole family can enjoy!
- Charming 4-bedroom house with WiFi, AC in pleasant Chesterfield
- Charming Retreat w/Pool Table in Chesterfield!
- Sleep Inn And Suites
- Sleep Inn & Suites Harbour Pointe
- Holiday Inn Express Hotel & Suites Richmond-Brandermill by IHG
2. Which vacation homes in Chesterfield are best for families?
If you are looking for a family-friendly vacation home in Chesterfield, 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:
3. How many Rentbyowner vacation rentals are available in Chesterfield?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 38 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.
4. What is the cancellation policy for vacation rentals in Chesterfield, Virginia?
Cancellation policies vary depending on the specific property listing. It’s recommended to review the cancellation terms listed on the property page or contact the owner directly to understand the options and any potential fees involved.
5. How do I ensure my booking is secure when reserving a vacation rental in Chesterfield, VA?
Secure bookings are guaranteed through verified listings and trusted payment methods. Always book through official channels, read reviews, and confirm the host's credentials to ensure a safe and reliable reservation process in the area.
6. Are there any additional fees I should be aware of when booking a vacation rental here?
Additional fees such as cleaning, service charges, or taxes may apply depending on the property. Be sure to check the detailed pricing information on the listing before completing your reservation to avoid surprises.
7. What amenities can I expect from vacation rentals in Chesterfield, Virginia?
Amenities vary by property but often include essentials like Wi-Fi, parking, fully equipped kitchens, and outdoor spaces. Check each listing carefully to ensure it offers the features you need for a comfortable stay in this region.
8. How far in advance should I book my stay in Chesterfield, VA during peak seasons?
It’s advisable to book several months ahead of your planned visit, especially during peak travel times, to secure the best selection and rates. For specific availability, contact the property owner or check the listing calendar directly.
