Photo by Nick Pagano

Chesterfield holiday rentals

We found 519 holiday rentals — enter your dates for availability

your current months are April, 2024 and May, 2024.
April 2024
May 2024
Discover a selection of 8 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.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

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:

  • Iron Bridge Sports Park (1.3 mi / 2.1 km)
  • Pocahontas State Park (3.9 mi / 6.2 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)
  • Richmond International Raceway (16.1 mi / 25.9 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:

  • Pocahontas State Park (3.9 mi / 6.2 km)
  • Richmond National Battlefield Park (8.1 mi / 13 km)
  • Maymont Park (11 mi / 17.7 km)
  • Dorey Park (11 mi / 17.8 km)
  • James River (11.1 mi / 17.9 km)
  • Virginia Capital Trail: Richmond Trailhead (11.3 mi / 18.2 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 most popular type of holiday home accommodation in Chesterfield?

The most popular types of holiday homes in Chesterfield are houses. Looking for something different? Stayz has many options to match the unique needs of our guests, so you'll see properties in lots of sizes and shapes. The perfect fit is waiting for you — get yours today.

How much does it cost to rent a holiday home in Chesterfield?

Different things can influence how much you'll pay for a holiday home in Chesterfield, such as the length of stay, season and type of property. Still, all of our holiday homes have something in common — exceptional value. Simply enter your travel dates to find your ideal match.

How much does it cost to rent a beach house in Chesterfield?

Prices for beach houses in Chesterfield may vary depending on the style and size of the property and when you plan to travel. Simply enter your dates of travel into Stayz and how many guests to view available options and prices. From there you can use our filters to tailor your search by amenities, nearby activities, ratings and more.

Are there pet-friendly holiday homes in Chesterfield?

There are, yes. You'll have your pick of four holiday homes that welcome pets in Chesterfield on Stayz. Our furry kids deserve a break too, so simply use our search function for pet-friendly holiday homes to find a property where Fido can get in on the fun.

What are popular home amenities in Chesterfield?

The most popular home amenities people are searching for in Chesterfield include a barbecue grill, a firepit and nearby museums. Whether you're taking a trip with buddies, family or even pets, Stayz holiday homes include the best amenities for ultimate relaxation with the people that matter most.

Are there large group holiday homes in Chesterfield?

There are two holiday properties in Chesterfield that can accommodate a group of five or more people. From family getaways to special occasions like birthday parties, these stays have enough room to spend time with your favourite people.

Are there holiday homes in Chesterfield that welcome kids?

Bring the whole family together for fun-filled adventures in Chesterfield at one of our four family-friendly holiday homes. Many of these stays feature conveniences that are suitable for trips with youngsters, such as full kitchens, extra bedrooms and entertainment units. Just click on the "Properties good for families" filter and decide on your favourite.

What are the top attractions for families in Chesterfield?

There's a ton of amazing things to see and do with the family in Chesterfield, such as:

  • Uptown Alley
  • River City Sportsplex
  • Pocahontas State Park

Are there holiday homes with WiFi in Chesterfield?

Chesterfield has three holiday homes with WiFi, so you can stay connected while you're on holiday. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming movies with the family to sending emails, these Stayz homes make it easy to get online.

How can I find holiday homes with air conditioning in Chesterfield?

You'll have a choice of three holiday homes with air conditioning in Chesterfield offering that cooling breeze and extra bit of comfort. Simply enter your dates of travel and then take advantage of our filters to help you find stays with air conditioning.

How old do you have to be to rent a holiday home in Chesterfield?

We advise checking with the Chesterfield holiday home you're looking at on Stayz as the minimum age differs. However, generally it's 16, 18 or 21.

How long can I rent a holiday home in Chesterfield for?

The length of time you can rent a holiday home in Chesterfield differs according to the property. Just enter your chosen travel dates to display a list of options offering extended stays. With a range of creature comforts such as air conditioning and full kitchens, as well as some offering weekly or monthly discounted prices, you're sure to get somewhere just right to call your home away from home in Chesterfield.

More Holiday Rentals ideas

People also search for