Best Vacation Homes in Chesterfield
House
10.0(17 Reviews)
5 Bedrooms
3 Baths
10 Guests
5354 ft²
Fireplace/Heating
Balcony/Terrace
Pet Friendly
Kitchen
US $474/Night
7 Nights - US $3,319
House
10.0(1 Review)
1 Bedroom
2 Baths
6 Guests
1539.24 ft²
- Fireplace/Heating
- Pet Friendly
Parking
Internet
US $169/Night
7 Nights - US $1,185
Hotel
9.4(310 Reviews)
1 Bath
- Fireplace/Heating
Pool- Balcony/Terrace
Breakfast
US $142/Night
7 Nights - US $993
House
10.0(13 Reviews)
1 Bedroom
1 Bath
6 Guests
1534 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $181/Night
7 Nights - US $1,269
Cabin
8.1(64 Reviews)
44 Bedrooms
5 Baths
12 Guests
292.78 ft²
- Pool
- Pet Friendly
- Parking
Air Conditioner
US $81/Night
7 Nights - US $565
Cottage
10.0(12 Reviews)
2 Bedrooms
2 Baths
5 Guests
1360 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $157/Night
7 Nights - US $1,101
House
10.0(12 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $102/Night
7 Nights - US $717
Cottage
10.0(4 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $258/Night
7 Nights - US $1,808
Chesterfield Luxury Rentals
US $487/Night
7 Nights - US $3,412
Apartment
2 Bedrooms
1 Bath
4 Guests
796.53 ft²
- Fireplace/Heating
- Parking
- Internet
Child Friendly
US $246/Night
7 Nights - US $1,720
Apartment
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $201/Night
7 Nights - US $1,404
Apartment
2 Bedrooms
1 Bath
4 Guests
796.53 ft²
- Fireplace/Heating
- Parking
- Internet
- Child Friendly
US $197/Night
7 Nights - US $1,381
House
2 Bedrooms
1 Bath
5 Guests
1004 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $165/Night
7 Nights - US $1,154
Apartment
9.0(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
800 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $148/Night
7 Nights - US $1,035
House
10.0(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $147/Night
7 Nights - US $1,030
Hotel
9.3(287 Reviews)
1 Bath
381.63 ft²
Oceanfront- Fireplace/Heating
- Pool
Ocean View
US $127/Night
7 Nights - US $887
Chesterfield Pet Friendly Vacation Rentals
Hotel
6.9(154 Reviews)
7 Baths
247.57 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $93/Night
7 Nights - US $651
US $81/Night
7 Nights - US $567
Chesterfield Large Vacation Homes
House
5.0(1 Review)
5 Bedrooms
4 Baths
10 Guests
5200 ft²
- Kitchen
- Air Conditioner
- Internet
Laundry
US $359/Night
7 Nights - US $2,513
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.
Best Times to Visit Chesterfield
When should you plan your Vacation Rentals stay?
Choosing the optimal time to vacation here can enhance your experience, allowing you to enjoy the region’s unique climate and seasonal charm while making the most of your stay in Chesterfield, South Carolina, USA.
Peak Season Highlights
Spring (March to May)
During the spring months, you can enjoy pleasant weather and blooming scenery, making it an ideal time to explore this destination's outdoor activities while staying in comfortable vacation rentals.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
Fall (September to November)
Fall offers cooler temperatures and vibrant foliage, attracting visitors who want to experience the region's natural beauty while staying in well-appointed vacation rentals.
Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F
Off-Season Highlights
Summer (June to August)
In the summer, the area experiences warmer weather that appeals to those seeking outdoor adventures and water-related activities, with vacation rentals offering a cool retreat after busy days.
Average Temperature Daytime: 85°F to 90°F - Nighttime: 65°F to 70°F
Winter (December to February)
During winter, you might find fewer crowds and more peaceful surroundings, perfect for relaxing in cozy vacation rentals while enjoying mild temperatures.
Average Temperature Daytime: 50°F to 60°F - Nighttime: 30°F to 40°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 grilling with a fully equipped barbecue area to savor meals during your stay.
- Relax by the private or shared swimming pool, perfect for cooling off in warm weather.
- Take advantage of spacious patios or decks ideal for outdoor dining and entertaining.
- Make use of well-maintained gardens or landscaped yards that offer a peaceful outdoor retreat.
- Access nearby walking trails or scenic paths to explore the natural beauty of the region.
- Benefit from outdoor recreational facilities such as volleyball courts or bocce ball areas.
- Appreciate the convenience of ample parking spaces for your vehicles during your visit.
Top Attractions Around Chesterfield
What attractions are nearby?
Enjoy a variety of outdoor activities nearby, from exploring scenic parks to engaging in recreational pursuits, all easily accessible from your rental here in Chesterfield, South Carolina, offering the perfect setting for a relaxing and adventurous getaway in the region.
Family Activities
- Chesterfield County Fairgrounds: Experience family-friendly events and entertainment that are perfect for creating lasting memories in this area.
- The Little Pee Dee River: Enjoy a relaxing day of fishing, kayaking, or picnicking along the river's scenic banks, ideal for outdoor family adventures.
- Carolina Memorial Park: Explore this peaceful park, offering wide open spaces and nature trails where your family can unwind and connect with the outdoors.
- Local Farmers Markets: Visit nearby markets to taste fresh produce and homemade treats, providing a fun and engaging activity for all ages.
Adult Activities
- Golfing at Chesterfield Golf Course: Enjoy a relaxing day on the links at one of the area's premier golf courses, perfect for both beginners and seasoned golfers.
- Exploring local history museums: Dive into the region’s rich heritage by visiting historical sites and museums that offer insight into its cultural background.
- Wildlife viewing in nearby parks: Experience the region's natural beauty through birdwatching and wildlife observation in scenic parks close to your rental.
Chesterfield Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining Options: Take advantage of the area's authentic cuisine by visiting nearby restaurants to enjoy regional flavors and support local businesses during your stay.
- Plan Outdoor Activities: Make the most of the region's natural beauty by scheduling outdoor adventures such as hiking or picnicking in nearby parks and scenic spots.
- Discover Nearby Attractions: Use your vacation rental as a base to explore lesser-known local sites and cultural landmarks that showcase the area's unique charm.
- Utilize Local Transportation: Consider renting bikes or using local transit options to navigate conveniently and experience the region like a local resident.
Transportation Options
- Chesterfield County Airport: This regional airport offers convenient air travel options for visitors heading to the area, making your journey smooth and efficient.
- Interstate 95: As a major highway passing through the region, I-95 provides easy road access for travelers arriving by car from multiple directions.
- South Carolina Bus Services: Local and regional bus lines connect this destination with surrounding cities, offering an affordable transportation choice within the region.
- Car Rentals at Nearby Locations: Numerous rental agencies in the area provide reliable vehicle options, giving you the flexibility to explore Chesterfield’s scenic surroundings at your own pace.
Local Customs Options
- Southern Hospitality: Embrace the warm and welcoming attitude typical in this region, where friendly gestures are a cherished part of local culture.
- Local Dining Customs: Enjoy the traditional Southern cuisine that emphasizes hospitality through shared meals and family-style dining experiences.
- Community Events: Engage with seasonal festivals and gatherings that highlight the area's cultural heritage and foster a sense of community among visitors.
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:
- Gorgeous, Southern Home in Beautiful Cheraw
- Bright Converted Schoolhouse in Chesterfield!
- Cozy Waterfront Retreat at McMichael Farms
- Cozy 2-bedroom townhome with WiFi, AC in charming Chesterfield
- 12 Acre Pond House Cottage in Chesterfield - come fish and paddle board! 2BR/2B
- 2 bedroom huntbox located on 220 acre farm close to H Cooper Black.
- The Cottage
- Vintage Villa Guesthouse
- Hike & Explore: Cheraw Apt 7 Mi to Lake Juniper!
- Bright Converted Schoolhouse in Chesterfield!
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, South Carolina?
Cancellation policies vary by property, so it's best to review the specific listing details or contact the property owner directly to understand the terms and any associated fees.
5. Are there any specific check-in and check-out times I should be aware of when booking here?
Check-in and check-out times are set by individual hosts; please consult your reservation details or communicate with the host for the exact timings related to your stay in this destination.
6. How do I find out about available amenities and services at a rental in Chesterfield?
Details about amenities and services are provided in each listing. Be sure to read the property description carefully or reach out directly to the host for any additional questions.
7. Can I bring pets to my vacation rental in this area?
Pet policies differ between properties, so it’s important to check the specific listing or contact the owner to confirm if pets are permitted during your visit.
8. What should I know about local regulations or requirements for staying in a vacation rental in this region?
Local regulations vary, so review the listing for any rules or requirements and consider reaching out to the owner for guidance on compliance to ensure a smooth stay.
Chesterfield Top Rated Vacation Rentals
US $91/Night
7 Nights - US $634
US $90/Night
7 Nights - US $633
