Chesterfield holiday lettings

We found 17 holiday rentals — enter your dates for availability

Discover a selection of holiday rentals in Chesterfield that are perfect for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday rentals have the amenities that you expect for your stay, which might include a garden and hot tub. At the end of the day, you'll be sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

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Find the perfect holiday rental for your Chesterfield getaway

Learn about the unique charm of Chesterfield with a stay in a holiday home rental. This city has something for everyone. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in Chesterfield

Are you searching for top things to see and do in the area? Venture out of your cosy holiday rental and experience everything that makes Chesterfield a one-of-a-kind holiday spot. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Cheraw State Park Golf Course (12.3 mi / 19.7 km)
  • Granny Hollow Pottery and Fancy Crafts (15.8 mi / 25.4 km)

Exploring the natural features in Chesterfield

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Chesterfield is a great place to spend some time outside. These are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Cheraw State Park (11.7 mi / 18.8 km)
  • H Cooper Black Jr. Memorial Field Trial & Recreation Area (15 mi / 24.2 km)
  • Dizzy Gillespie Park (11.3 mi / 18.3 km)
  • Little Park (17.5 mi / 28.2 km)
  • Caston Park (11.5 mi / 18.5 km)

Frequently asked questions

What is the best area to stay in Chesterfield when booking a holiday rental?
When considering a holiday rental in Chesterfield, South Carolina, the town centre is an excellent choice for your stay. This area offers a charming small-town atmosphere combined with convenient access to various amenities. You'll find a selection of properties that cater to different preferences, providing a comfortable base for your holiday.

One of the highlights of staying in the town centre is its proximity to attractions such as the Chesterfield Museum, which showcases the rich history of the area, and the scenic Chesterfield County Courthouse, an architectural gem that reflects the region's heritage. Additionally, the nearby parks offer lovely green spaces for leisurely strolls or picnics, making it easy to unwind amidst nature.
How much does it cost to rent a holiday home in Chesterfield?
Prices for holiday rentals in Chesterfield vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Chesterfield to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Chesterfield holiday house rentals?
You can find great discounts on house rentals in Chesterfield on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of holiday rental accomodation in Chesterfield?
In Chesterfield, cottages are a popular choice among holiday rentals, with several available throughout the area. These charming properties often feature rustic decor, fully equipped kitchens, and cosy living spaces, great for a relaxing getaway. Many cottages also come with outdoor seating areas, allowing guests to enjoy the serene surroundings.

Holiday houses are another common option, also numbering several in the region. These homes typically offer more space and amenities, including multiple bedrooms and private gardens, ideal for families or larger groups looking for a comfortable stay. Cabins, while also available in several numbers, provide a great experience with a focus on nature, often located near scenic spots for outdoor activities.
Are there any family house rentals in Chesterfield?
In Chesterfield, South Carolina, there are several family-friendly house rentals available, suiting those seeking a comfortable stay. The area features homes that offer spacious living rooms, fully equipped kitchens for preparing family meals, and outdoor areas where children can play. Many of these properties come with essential amenities such as Wi-Fi and air conditioning, ensuring a pleasant experience for visitors.

Nearby, families can explore local parks and enjoy outdoor activities, making it a great destination for those looking to connect with nature and engage in recreational fun.
Can I find long-stay holiday rentals in Chesterfield?
A long-stay holiday rental in Chesterfield is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there any remote work holiday rentals in Chesterfield?
In Chesterfield, South Carolina, there are approximately 10 remote work holiday rentals available, making it a suitable destination for those looking to blend work and leisure. Many of these properties are equipped with essential amenities for remote work, including Wi-Fi in rooms and public areas, dedicated laptop workspaces, and desks to ensure a productive environment.

Travellers can expect a variety of options ranging from comfortable homes to more modern accommodations, all designed to cater to the needs of working professionals. Chesterfield itself offers a quaint small-town atmosphere with local parks and recreational areas nearby, providing opportunities for relaxation after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chesterfield holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Chesterfield with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Chesterfield?
In Chesterfield, popular rental amenities include kitchens, which allow guests to prepare their own meals, and coffee or tea makers for a refreshing start to the day. Onsite parking is typically available, making it convenient for those travelling with vehicles. Many rentals are also pet-friendly, accommodating furry companions, and allow service animals as well.
When is the best time to visit Chesterfield for a holiday rental?
The best time to visit Chesterfield for a holiday rental is during the peak season from March to May, with May being particularly popular. This period invites travellers seeking warm weather and vibrant blooms, making it ideal for outdoor activities and exploring the picturesque landscapes of South Carolina.

During these months, temperatures generally range from the low teens to mid-20s Celsius, providing a comfortable climate for sightseeing, hiking, and enjoying local festivals. The region comes alive with various events, offering an excellent opportunity to immerse yourself in the community spirit and experience the charm of Chesterfield.

If you're looking for a more budget-friendly option, consider visiting in October. This month offers a quieter atmosphere with mild temperatures, superb for leisurely walks and appreciating the changing colours of autumn. It's a great time to explore local attractions without the hustle and bustle of peak tourist traffic.
How early should I book a Chesterfield holiday rental?
Book your Chesterfield holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Chesterfield?
In Chesterfield, South Carolina, visitors can enjoy a variety of attractions that highlight the area's natural beauty and local charm. The Chesterfield County Historical Museum offers insights into the region's history and features exhibits that showcase local artefacts. For those interested in outdoor activities, the nearby Cheraw State Park is a popular spot, offering opportunities for hiking, fishing, and kayaking, all set against the backdrop of beautiful landscapes.

The town's proximity to the Great Pee Dee River provides additional recreational options, including boating and picnicking along the riverbanks. Additionally, Chesterfield hosts various community events throughout the year, allowing visitors to experience local culture and traditions.
Can I change or cancel my Chesterfield home rental booking on Vrbo?
To find Chesterfield holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Chesterfield holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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