Chesterfield holiday lettings

We found 627 holiday rentals — enter your dates for availability
Discover a selection of 6 homes and other holiday rentals in Chesterfield that are perfect for your trip. Holiday homes offer the best amenities for your family, friends or furry companion, such as Wi-Fi and cable TV. No matter what you're looking for, you'll be sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Chesterfield

Showing deals for:5 Feb - 12 Feb

Image gallery for Luxurious riverfront Manor with 6 bedrooms and WiFi, AC in fabulous Midlothian

Property grounds
10 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)

Luxurious riverfront Manor with 6 bedrooms and WiFi, AC in fabulous Midlothian

Midlothian

8% off
Price is £9,213
for 7 nights, 1 home
£1,316 per night
includes taxes & fees
Luxurious riverfront Manor with 6 bedrooms and WiFi, AC in fabulous Midlothian

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    Enjoy full kitchens, pools, gardens and more

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The natural setting of Chesterfield is ready to explore

Take a holiday to Chesterfield and enjoy the area's culture, history and museums. Renowned for its shopping, golfing and parks, this city welcomes all visitors. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Chesterfield

Do you want to find attractions to see while you're in the area? Venture out of your cosy holiday rental and experience everything that makes Chesterfield a fun spot to go on holiday. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Pocahontas State Park (3.9 mi / 6.2 km)
  • Libby Hill Park (11.5 mi / 18.4 km)
  • Capitol Square (11.8 mi / 19 km)
  • Country Club of Virginia (13.4 mi / 21.6 km)
  • Metro Richmond Zoo (14.3 mi / 23.1 km)
  • Virginia Motorsports Park (14.6 mi / 23.4 km)

Exploring the natural landscape of Chesterfield

Whether you're an adventurous traveller or just want to take in the scenery, Chesterfield is a great place to get out in nature. These are some of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Dorey Park (11 mi / 17.8 km)
  • Maymont Park (11.1 mi / 17.8 km)
  • James River (11.1 mi / 17.9 km)
  • Virginia Capital Trail: Richmond Trailhead (11.3 mi / 18.2 km)
  • Libby Hill Park (11.5 mi / 18.4 km)
  • Pamplin Historical Park (13.6 mi / 21.9 km)

Travelling to and around Chesterfield

The nearest airport is in Richmond, VA (RIC-Richmond Intl.), located 13.1 mi (21.1 km) from the city centre.

Frequently asked questions

What is the best area to stay in Chesterfield when booking a holiday rental?
When considering a holiday rental in Chesterfield, Virginia, a popular area to stay is near the Swift Creek Reservoir. This picturesque location not only offers a tranquil setting but also provides easy access to various outdoor activities such as hiking, biking, and fishing. The surrounding neighbourhoods are family-friendly and boast a range of properties, from spacious homes to charming townhouses.

Another great option is the area around Chesterfield Town Centre, which is great for those who enjoy shopping and dining. Here, you'll find an array of retail shops, restaurants, and entertainment options, making it a lively spot to base your holiday. Additionally, the nearby Pocahontas State Park is a fantastic attraction, offering beautiful trails, picnic areas, and historical sites that can enrich your stay.
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 holiday rental, with about 14 available throughout the area. These homes typically feature spacious layouts, including multiple bedrooms and fully equipped kitchens, making them ideal for families or groups seeking a comfortable stay. Many of these properties also offer outdoor spaces for relaxation, such as patios or gardens. Additionally, there are several apartments scattered across the neighbourhood, providing a convenient alternative for those preferring a more compact living arrangement.
Are there any family house rentals in Chesterfield?
In Chesterfield, Virginia, there are several family-friendly house rentals available, making it an inviting destination for groups seeking a comfortable stay. Many of these properties are located in neighbourhoods that offer spacious living areas, well-equipped kitchens, and outdoor spaces where children can play or families can enjoy barbecues. Visitors can expect amenities such as Wi-Fi and air conditioning, ensuring a relaxing environment.

The area is also close to attractions like Pocahontas State Park, which features hiking trails, picnic areas, and lakes superb for family outings. Additionally, the nearby Chesterfield Town Centre provides shopping and dining options for those looking to explore local cuisine and retail.
Can I rent a holiday home with a pool or hot tub in Chesterfield?
In Chesterfield, Virginia, there are several holiday homes available for rent that feature pools and hot tubs. This suburban area offers a variety of neighbourhoods where these properties can be found, providing options for families or groups seeking relaxation and leisure. Many of the rentals come with amenities such as private pools, spacious outdoor areas, and fully equipped kitchens, making them ideal for entertaining or enjoying a peaceful retreat. Additionally, some homes may include hot tubs, superb for unwinding after a long day.
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, there are several pet-friendly house rentals available for those travelling with furry companions. Many of these properties offer spacious living areas, fully equipped kitchens, and outdoor spaces such as private yards or patios, ideal for pets to enjoy. The rentals often come with amenities like laundry facilities, Wi-Fi, and comfortable furnishings, ensuring a pleasant stay for both humans and pets alike.

The surrounding area features various parks and recreational facilities, great for walks and outdoor activities with pets. Notable spots include the extensive Chesterfield County parks, where you can find trails and open spaces to explore.
Are there any remote work holiday rentals in Chesterfield?
In Chesterfield, Virginia, there are approximately 14 holiday rentals that cater to remote workers. These properties typically offer essential amenities such as free Wi-Fi and reliable internet access, ensuring that guests can stay connected while working from the comfort of their accommodation. Many rentals feature dedicated workspaces or comfortable living areas ideal for productivity.

Chesterfield is conveniently located near various points of interest, including parks and shopping areas, which provide opportunities for relaxation and leisure after work hours. Additionally, local dining establishments and recreational facilities are within easy reach, making it a great choice for those looking to blend work and leisure during their stay. 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 onsite parking, which provides convenience for guests with vehicles. Many holiday rentals feature kitchens, allowing travellers to prepare their own meals, and a coffee or tea maker is often included for that morning caffeine boost. Additionally, rentals typically come with a deck or patio, offering outdoor space to relax, and dining areas where guests can enjoy meals together.
When is the best time to visit Chesterfield for a holiday rental?
The peak season for visiting Chesterfield, Virginia, spans from May to July, with July being the most popular month for holiday rentals. This is when the area comes alive, attracting families and adventure-seekers eager to explore its rich history and vibrant outdoor activities. The warm summer temperatures (averaging around 25 to 30 degrees Celsius) create a friendly space for sightseeing and enjoying local parks, such as the beautiful Pocahontas State Park, where hiking and picnicking opportunities abound.

During the peak season, Chesterfield hosts numerous events and festivals, providing an excellent chance to mingle with locals and immerse yourself in the community spirit. The long summer days offer ample time for outdoor pursuits, making it ideal for families looking to create lasting memories.

For those seeking a more budget-friendly option, consider visiting in December. While this month may be quieter, it presents a unique charm with holiday festivities and a chance to experience Chesterfield's seasonal decorations without the crowds. Plus, this time can offer cosy winter getaways, great for enjoying local cuisine and visiting nearby attractions at a leisurely pace.
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, Virginia, visitors can explore a variety of attractions that highlight the area's natural beauty and rich history. The Chesterfield County Museum offers insights into the region's past, featuring exhibits that showcase local history and heritage. Nearby, the historic site of the Battle of Chesterfield provides a glimpse into the Civil War era, with informative markers and walking trails.

For outdoor enthusiasts, Pocahontas State Park is a significant draw, offering hiking trails, fishing opportunities, and a serene lake for kayaking and canoeing. The park's natural setting makes it a wonderful spot for picnics and enjoying the local flora and fauna.

Families may also enjoy a visit to the Chesterfield Towne Centre, where shopping, dining, and entertainment options abound. The centre features a variety of stores and restaurants, suiting diverse tastes and preferences.
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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