Photo by Nick Pagano

Chesterfield holiday lettings

We found 566 holiday rentals — enter your dates for availability

Discover a selection of 7 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:26 Dec - 2 Jan

Image gallery for Luxurious 1-bedroom riverfront Cottage with AC and WiFi in charming Midlothian.

Exterior
10 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)

Luxurious 1-bedroom riverfront Cottage with AC and WiFi in charming Midlothian.

Midlothian, VA

7% off
Price is £3,845
for 7 nights, 1 cottage
£549 per night
includes taxes & fees
Luxurious 1-bedroom riverfront Cottage with AC and WiFi in charming Midlothian.

Find spaces that suit your style

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  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find out more about Chesterfield

Find out more about Chesterfield

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)
  • Petersburg National Battlefield Park (12.9 mi / 20.8 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:

  • Richmond National Battlefield Park (8.1 mi / 13 km)
  • 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)

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 close to the Midlothian neighbourhood. This area offers a charming suburban feel combined with convenient access to various attractions. Midlothian is known for its picturesque landscapes and family-friendly atmosphere, making it an excellent choice for travellers seeking a relaxing getaway.

Nearby, you can explore the Midlothian Mines Park, where you can enjoy scenic walking trails that weave through historical remnants of the area's mining past. Another delightful spot is the Chesterfield Town Centre, which boasts a myriad of shops and dining options, superb for an enjoyable day out.
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, with several available throughout the area. These homes typically offer spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups looking for a comfortable home base. Many of these properties also feature outdoor spaces, such as gardens or patios, great for relaxing after a day of exploring the local attractions. Additionally, apartments and mobile homes are also available, providing travellers with a variety of options to suit their needs.
Are there any family house rentals in Chesterfield?
In Chesterfield, Virginia, there are several family-friendly house rentals to choose from, making it an excellent choice for those travelling with children. The neighbourhoods around the area offer various spacious homes equipped with essential amenities. Many of these properties feature multiple bedrooms, generous living spaces, and fully equipped kitchens, great for preparing family meals.
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 mix of residential neighbourhoods, making it a great choice for travellers seeking relaxation and comfort. Many of these properties come equipped with private pools, spacious outdoor areas for entertaining, and hot tubs for unwinding after a long day of exploring.
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, suiting travellers seeking a comfortable stay with their furry companions. Many of these rentals are equipped with modern amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces where pets can play.
Are there any remote work holiday rentals in Chesterfield?
In Chesterfield, Virginia, there are several holiday rentals suitable for remote work. Many of these properties come equipped with essential amenities such as Wi-Fi, dedicated desks, and comfortable desk chairs, ensuring a productive environment for those working away from their usual office. The area offers a range of options, from contemporary apartments to spacious homes, allowing travellers to choose accommodations that best fit their needs. 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 holiday rental amenities include free Wi-Fi, coffee makers, and well-equipped kitchens featuring cookware, dishware, and utensils. Most rentals also come with refrigerators, ensuring guests have the convenience of preparing their own meals during their stay.
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.
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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