Chesterfield holiday lettings

We found 16 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 out more about Chesterfield

Find out more about Chesterfield

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)
  • Caston Park (11.5 mi / 18.5 km)
  • Little Park (17.5 mi / 28.2 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, a popular area to stay is near the charming downtown district. This area not only offers a quaint atmosphere with its historic buildings but also provides easy access to various local shops and eateries. Staying here allows you to immerse yourself in the community vibe while being just a short distance from attractions such as the Chesterfield County Historical Society Museum, which showcases the rich history of the region, and the nearby Cheraw State Park, great for outdoor enthusiasts seeking hiking, fishing, and picnic opportunities.
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, holiday houses are the most popular type of rental accommodation, with several available in the area. These properties typically provide ample space and amenities, including fully equipped kitchens, spacious living areas, and outdoor spaces for relaxation. Many holiday houses are set in tranquil neighbourhoods, making them ideal for families or groups looking for a peaceful retreat. Additionally, there are several cottages and cabins that offer a charming, rustic experience, often featuring unique character and proximity to nature.
Are there any family house rentals in Chesterfield?
In Chesterfield, South Carolina, there are several family-friendly house rentals available, making it an appealing destination for those travelling with children. The area offers a variety of spacious homes equipped with essential amenities such as full kitchens, comfortable living rooms, and outdoor areas where families can gather and enjoy the fresh air.
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 pet-friendly house rentals in Chesterfield?
In Chesterfield, South Carolina, there are several pet-friendly house rentals available, offering a warm and inclusive setting for both you and your furry companions. Many of these holiday homes come equipped with amenities such as spacious backyards, which are great for pets to roam freely, as well as fully equipped kitchens and comfortable living areas that cater to families or groups.
Are there any remote work holiday rentals in Chesterfield?
In Chesterfield, South Carolina, there are several remote work-friendly holiday rentals available, suiting those looking to blend work and leisure. Many of these properties come equipped with essential amenities such as reliable Wi-Fi, dedicated desk spaces, and laptop workstations, ensuring a comfortable and productive environment for remote workers. 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 essential kitchen facilities such as cookware, dishware, and utensils, allowing guests to prepare their own meals. Many properties are equipped with microwaves for quick heating, and free Wi-Fi is commonly available, enabling travellers to stay connected during their stay.
When is the best time to visit Chesterfield for a holiday rental?
The best time to book a holiday rental in Chesterfield is during the peak season from March to May, with May being the most popular month. This period attracts visitors eager to enjoy the mild spring weather, with temperatures typically ranging from the high teens to low 20s Celsius, making it ideal for outdoor activities and exploring the picturesque surroundings.

During these months, Chesterfield comes alive with various local events and activities. The blossoming flora enhances the natural beauty of the area, superb for leisurely strolls, picnics, or hiking in the nearby parks. This season provides a vibrant atmosphere, as you'll find fellow travellers sharing in the enjoyment of Chesterfield's charm.

If you're looking for a more budget-friendly option, consider planning your visit in October. This month offers a quieter experience, allowing you to appreciate the changing leaves and the tranquil beauty of the landscape without the hustle and bustle of peak tourist activity.
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 several attractions that highlight the area's charm and history. The Chesterfield County Museum provides insights into the local heritage, featuring exhibits on the region's past and culture. Nearby, the picturesque Cheraw State Park offers opportunities for outdoor activities such as hiking, fishing, and boating, making it a lovely spot for nature enthusiasts.
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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.

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