Chesterfield vacation rentals

We found 633 vacation rentals — enter your dates for availability

Discover a selection of 8 homes and other vacation rentals in Chesterfield that are perfect for your trip. Vacation homes offer the best amenities for you and your friends, family, or even pets, like WiFi and cable TV. At the end of the day, you'll be sure to find a rental for everyone's needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Chesterfield

Showing deals for:Jul 3 - Jul 10

Image gallery for Nice! New home near VSU x Fort Lee Military Base mins to DT Richmond VA

Living area
10 out of 10, Exceptional, (15 reviews)
Exceptional
(15 reviews)

Nice! New home near VSU x Fort Lee Military Base mins to DT Richmond VA

Petersburg

8% off
Price is $346
$2,423 for 7 nights
All fees included
Nice! New home near VSU x Fort Lee Military Base mins to DT Richmond VA

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Find out more about Chesterfield

Why visit Chesterfield

  • Family-Friendly Attractions: Enjoy a variety of activities suitable for all ages, making it a perfect destination for family vacations.
  • Outdoor Adventures: Explore beautiful parks and natural areas, offering opportunities for hiking, picnicking, and wildlife viewing.
  • Historic Sites: Discover the rich history of Chesterfield through its various historic landmarks and museums.
  • Shopping and Dining: Experience local shops and dining options that showcase the unique flavors of the community.
  • Convenient Location: Benefit from Chesterfield's proximity to Richmond, allowing for easy exploration of the city and its attractions.

Popular types of accommodation in Chesterfield

If you're planning a getaway to Chesterfield, you're in for a treat. Our most popular vacation rental options include charming cottages, houses, and cozy apartments. Many of these rentals feature inviting living rooms and offer the convenience of free parking. Discover the perfect home base for your adventures in Chesterfield, where comfort and relaxation await you.

  • Houses: The top choice for travelers, these homes offer ample space and privacy, perfect for families or groups seeking a home-away-from-home experience.
  • Apartments: A popular option, apartments provide convenience and a cozy atmosphere, ideal for couples or solo travelers looking for a comfortable stay.
  • Condos: These stylish accommodations blend luxury with practicality, making them a favored option for those wanting a bit more sophistication.
  • House Boats: For a unique experience, house boats offer a charming stay on the water, combining relaxation with adventure.
  • Cabins: Rustic and serene, cabins are perfect for nature lovers seeking a peaceful retreat in Chesterfield.**

Top attractions in and around Chesterfield

Chesterfield, Virginia, offers a delightful blend of family-friendly, city-themed, and outdoor activities. Visitors can explore a variety of attractions, including urban parks, national state parks, and historic sites. Whether you're seeking cultural experiences or outdoor adventures, Chesterfield caters to all types of travelers, making it an ideal destination for anyone looking to enjoy their vacation.

  • Pocahontas State Park: This expansive park offers a blend of lush scenery and outdoor adventure, featuring hiking trails, fishing spots, and picnic areas. It's perfect for nature lovers seeking to explore Virginia's stunning landscapes.
  • James River: Located 11 miles away, this picturesque river is ideal for kayaking, fishing, and enjoying scenic views. Its tranquil atmosphere invites visitors to connect with nature and unwind.
  • Maymont Park: This historic private garden, also 11 miles away, features beautiful landscapes, gardens, and a mansion. It offers a glimpse into the region's rich history and is perfect for leisurely strolls.

Things to do recommended for couples

For a romantic getaway in Chesterfield, consider a visit to the Country Club of Virginia, just 13 miles away. Indulge in luxury vibes while enjoying a meal, or take a leisurely stroll through the beautiful grounds for a perfect couple's escape.

Things to do recommended for families

Families visiting Chesterfield can explore the fun at the Metro Richmond Zoo, featuring animal encounters and a playground. Enjoy outdoor adventures at Pocahontas State Park, perfect for hiking and picnicking, or visit the Chesterfield County Museum to learn about local history in an engaging way.

Things to do recommended for groups

Groups visiting Chesterfield can enjoy a fun day at the Pocahontas State Park, exploring scenic trails and picnicking by the lake. Additionally, the Chesterfield County Fair offers local food, rides, and entertainment, perfect for a lively group experience.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Chesterfield

When planning your trip, whether you're traveling with a group, family, pets, or seeking extended stays, it's important to prioritize your preferences. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Chesterfield with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Chesterfield with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Chesterfield: For many families, a getaway isn’t truly satisfying unless their furry companion is along for the adventure. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with food bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Chesterfield: If you're in search of vacation rentals that offer great deals for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to enhance your search.

Where to stay in and around Chesterfield

Chesterfield, Virginia, offers a delightful blend of family-friendly attractions and outdoor adventures. Visitors can explore the beautiful Chesterfield County, enjoy shopping at local stores, and experience the warm atmosphere of friendly neighborhoods. With its convenient location near Richmond, Chesterfield is perfect for those seeking an exciting city-themed vacation or a relaxing family getaway. Dive into the adventure and create lasting memories in this charming area.

  • Chester: Located a mere 4 miles from Chesterfield, Chester is a vibrant city that offers a delightful mix of family-friendly activities and business-oriented venues. Visitors can enjoy a day at the local shopping mall or explore the arcade adventure zone for some fun. The area is rich in history, with nearby attractions such as a historic college university, a stadium for sports enthusiasts, and an exciting theme park that promises a day of thrills. Chester’s accessible amenities make it an ideal stop for both leisure and business travelers.
  • Chesterfield Court House: Nestled within Chesterfield, Chesterfield Court House is a charming village that beckons outdoor enthusiasts and nature lovers. Known for its scenic beauty, this area provides ample opportunities for adventure with its recreational areas and parks. Visitors can immerse themselves in the great outdoors, with attractions like a national state park and various historical sites nearby. The village’s serene environment encourages exploration and relaxation, making it a perfect getaway for those looking to reconnect with nature.
  • Bellwood: Just 5 miles from Chesterfield, Bellwood is a bustling neighborhood that caters to families and business travelers alike. With accessible shopping centers and recreational areas, it offers a blend of urban convenience and leisure activities. Highlights include an event conference venue and a modern convention center, making it an excellent choice for those visiting for work or events. Urban parks in the vicinity provide a refreshing escape, making Bellwood a prime destination for both relaxation and productivity.

Best time to go to Chesterfield

If you're planning a trip to Chesterfield, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April and June to July, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January38.3°F (3.5°C)Light RainMostly SunnySlightly LowSlightly Low
February41.9°F (5.5°C)Light RainMostly SunnyAverageSlightly Low
March48.6°F (9.2°C)Light RainMostly SunnyAverageAverage
April58.6°F (14.8°C)Light RainMostly SunnySlightly HighSlightly Low
May67.3°F (19.6°C)Light RainMostly SunnyAverageSlightly High
June75.6°F (24.2°C)Light RainMostly SunnySlightly HighAverage
July80.1°F (26.7°C)Light RainMostly SunnySlightly HighAverage
August77.9°F (25.5°C)Light RainMostly SunnyAverageSlightly High
September72.1°F (22.3°C)Light RainMostly SunnyAverageAverage
October61.5°F (16.4°C)Light RainMostly SunnyAverageAverage
November49.8°F (9.9°C)Light RainMostly SunnySlightly LowSlightly High
December43.3°F (6.3°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is a breeze

Are you interested in saving money on your next trip? Being flexible with your travel dates can lead to better deals, as prices often fluctuate. Additionally, consider booking a longer stay to enjoy considerable savings. To discover a Vrbo property that aligns with your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers a user-friendly area to plan new trips, continue from where you last stopped, or review and organize your travel plans. You'll find your saved or booked properties neatly organized into categories: Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

The natural setting of Chesterfield is ready to explore

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

Activities and attractions in Chesterfield

Are you hoping to discover attractions to visit while you're in town? Venture out of your vacation home and experience everything that makes Chesterfield a one-of-a-kind vacation spot. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Pocahontas State Park (3.9 mi / 6.2 km)
  • Rockwood Park (6.6 mi / 10.7 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)

Exploring the natural landscape of Chesterfield

Whether you're an adventurous traveler or just want to spend some time taking in the scenery, Chesterfield is a great place to spend some time outside. Here are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city center:

  • Rockwood Park (6.6 mi / 10.7 km)
  • 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)

Traveling to and around Chesterfield

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

Frequently asked questions

What is the best area to stay in Chesterfield, Virginia, United States of America when booking a vacation rental?
When looking for the best area to stay in Chesterfield, Virginia, consider exploring the neighborhoods of Chester and Midlothian. Chester offers a charming suburban feel with easy access to the scenic James River, making it a great spot for outdoor enthusiasts. You can enjoy leisurely walks or picnics at the nearby Riverfront Park, which features beautiful views and recreational activities.

On the other hand, Midlothian boasts a vibrant mix of shopping, dining, and entertainment options. You'll find popular attractions like the historic Midlothian Mines Park, where you can delve into the area's rich history while enjoying picturesque trails. Both neighborhoods provide a range of vacation rental properties, suiting different tastes and budgets, ensuring you find a comfortable place to unwind after a day of exploring.
How much does it cost to rent a vacation home in Chesterfield?
Prices for vacation 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 vacation 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 vacation rental accomodation in Chesterfield?
In Chesterfield, vacation houses and apartments are both popular choices, with several options available in the area. The vacation houses typically feature spacious layouts, multiple bedrooms, and outdoor spaces, making them ideal for families or groups seeking a comfortable stay. Many of these homes come equipped with amenities such as fully stocked kitchens, laundry facilities, and sometimes private yards for relaxation. On the other hand, the apartments in Chesterfield often cater to travelers looking for a more compact and convenient option. These usually include essential amenities like kitchens, living areas, and sometimes access to shared facilities such as pools or fitness centers.
Are there any family house rentals in Chesterfield?
In Chesterfield, Virginia, there are several family-friendly house rentals available, making it a great choice for those traveling with kids. The area features spacious homes that often come with multiple bedrooms, allowing for plenty of room for everyone. Many of these properties include amenities such as full kitchens, so families can prepare their own meals, and comfortable living areas superb for relaxing after a day of exploring.

Proximity to points of interest adds to the appeal; for instance, nearby parks like Pocahontas State Park offer trails for hiking and biking, as well as picnic areas for family outings. Additionally, the local community is home to various attractions, including museums and family-friendly restaurants.
Can I rent a vacation home with a pool or hot tub in Chesterfield?
In Chesterfield, Virginia, there are several vacation homes available for rent that feature pools and hot tubs. This suburban area offers a variety of neighborhoods where travelers can find these amenities, providing options for relaxation and entertainment. Many properties typically come with spacious outdoor areas, superb for enjoying warm weather, as well as fully equipped kitchens for convenient meal preparation. Additionally, some rentals may include features like outdoor seating areas, barbecue grills, and cozy living spaces, making them suitable for family gatherings or group retreats.
Can I find long-stay vacation rentals in Chesterfield?
A long-stay vacation rental in Chesterfield is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Chesterfield?
In Chesterfield, Virginia, travelers will find several pet-friendly house rentals that cater to families and groups. Many of these homes come equipped with spacious backyards, allowing pets to roam freely, as well as amenities such as fully equipped kitchens, cozy living areas, and outdoor spaces for relaxation.

The neighborhood offers a suburban charm with easy access to parks and recreational areas. Notable nearby locations include the scenic Chesterfield County Parks, which feature walking trails, picnic areas, and open spaces superb for walks with pets. Additionally, many local restaurants and shops are welcoming to furry companions, ideal for pet owners.
Are there any remote work vacation rentals in Chesterfield?
In Chesterfield, Virginia, there are several remote work-friendly vacation rentals available that cater to the needs of travelers looking to work while enjoying their stay. These properties typically include essential amenities such as dedicated desk spaces, comfortable chairs, and reliable Wi-Fi, ensuring a productive environment. Many rentals also offer additional conveniences like fully equipped kitchens, allowing for easy meal preparation, and inviting living areas where one can unwind after a day of work. The area itself is known for its suburban charm, with nearby parks and recreational areas providing opportunities for relaxation and outdoor activities. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chesterfield vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Chesterfield with parking available—perfect for families or travelers 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 vacation rental amenities include onsite parking, which is convenient for travelers with vehicles. Most rentals are equipped with kitchen facilities, allowing guests to prepare their own meals, and many also feature coffee and tea makers for those who enjoy a warm beverage in the morning. Additionally, properties often come with a deck or patio, providing outdoor space to relax and enjoy the surroundings. Dining areas are also a common feature, making it easy for guests to gather for meals.
When is the best time to visit Chesterfield for a vacation rental?
The best time to visit Chesterfield for a vacation rental is during the peak travel season from May to July. This period draws families and travelers eager to enjoy the warm weather and vibrant local events. With temperatures typically ranging from the mid-70s to the low 90s Fahrenheit, Chesterfield offers a comfortable climate superb for outdoor activities, including hiking and exploring the beautiful parks in the area.

July is particularly popular, when the community comes alive with summer festivals and outdoor concerts. You can soak in the local culture while enjoying the scenic surroundings, making it an ideal choice for those seeking a lively option and numerous recreational opportunities.

If you're looking for a more budget-friendly option, consider visiting in December. While this month is part of the low season, it offers a unique charm with holiday festivities. You can enjoy a quieter experience while taking in the seasonal decorations and exploring the local attractions at a leisurely pace.
How early should I book a Chesterfield vacation rental?
Book your Chesterfield vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Chesterfield, Virginia, United States of America?
In Chesterfield, Virginia, visitors can explore a variety of attractions that showcase the area's natural beauty and historical significance. The Chesterfield Historical Society offers a glimpse into the region's past, featuring exhibits and tours that highlight local history. Nearby, the Chesterfield County Museum provides additional insights into the area's heritage.

For outdoor enthusiasts, the Pocahontas State Park is a significant draw, offering miles of hiking and biking trails, as well as opportunities for fishing and camping. The park's beautiful landscapes make it a superb spot for a day of outdoor activities.

Families can enjoy the fun at the River City Sportsplex, which hosts various sporting events and activities throughout the year. Additionally, the local shopping scene at places like the Chesterfield Towne Center offers a range of retail options and dining experiences.
Can I change or cancel my Chesterfield home rental booking on Vrbo?
To find Chesterfield vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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