Chesterfield holiday homes

We found 620 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:18 Dec - 25 Dec

Property grounds
Property grounds
Interior
Interior
Exceptional
(6 reviews)

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

Midlothian

5% off
NZ$26,572
for 7 nights, 1 home
NZ$3,796 per night
includes taxes & fees
Luxurious riverfront Manor with 6 bedrooms and WiFi, AC in fabulous Midlothian
Living area
Private kitchen
Living area
Dining
Excellent
(13 reviews)

Spacious 5BD 5.5BA house in the Heart of Richmond

Richmond

16% off
NZ$8,410
for 7 nights, 1 home
NZ$1,201 per night
includes taxes & fees
Spacious 5BD 5.5BA house in the Heart of Richmond
A step back in time welcomes you.
Pool
Exterior
Pool
Exceptional
(52 reviews)

Historic Marshall house w/3 King sized beds, 11 total beds & saltwater Pool

Richmond

8% off
NZ$15,624
for 7 nights, 1 home
NZ$2,232 per night
includes taxes & fees
Historic Marshall house w/3 King sized beds, 11 total beds & saltwater Pool
Living Room
Patio
King Size Bed
Games room
Exceptional
(29 reviews)

A Clean, Safe, House full of steel balls & vintage game consoles

Richmond

8% off
NZ$7,398
for 7 nights, 1 home
NZ$1,057 per night
includes taxes & fees
A Clean, Safe, House full of steel balls & vintage game consoles
Private kitchen
Exterior detail
Living area
Room
Exceptional
(7 reviews)

Adorable Cottage + Convenient & Quiet + Excellent Location

Richmond

8% off
NZ$2,504
for 7 nights, 1 home
NZ$358 per night
includes taxes & fees
Adorable Cottage + Convenient & Quiet + Excellent Location
Private kitchen
Living area
Dining room
Family Room
Very good
(10 reviews)

Pet-friendly spacious home with parking! Large deck & close to major attractions

Richmond

7% off
NZ$2,558
for 7 nights, 1 home
NZ$365 per night
includes taxes & fees
Pet-friendly spacious home with parking! Large deck & close to major attractions
Dining
Private kitchen
Private kitchen
Living area
Exceptional
(9 reviews)

Modern 3-bedroom 3 bathroom Retreat

Richmond

12% off
NZ$8,010
for 7 nights, 1 home
NZ$1,144 per night
includes taxes & fees
Modern 3-bedroom 3 bathroom Retreat
Dining table with seating for 6 and lots of historic charm
Living area
Room
Living area
Exceptional
(10 reviews)

Charming Historic Home-Walk to Carytown-Fence-Pet Friendly-Hotel-grade Towels

Richmond

8% off
NZ$6,062
for 7 nights, 1 home
NZ$866 per night
includes taxes & fees
Charming Historic Home-Walk to Carytown-Fence-Pet Friendly-Hotel-grade Towels
Interior
Interior
Property grounds
Room
Exceptional
(17 reviews)

Cozy Barndominium Guest Home

Amelia Court House

6% off
NZ$1,969
for 7 nights, 1 room
NZ$281 per night
includes taxes & fees
Cozy Barndominium Guest Home
Room
Living area
Living area
Exterior
Exceptional
(11 reviews)

Luxe Club RVA: Glam 2BR Escape

Richmond

5% off
NZ$2,298
for 7 nights, 1 home
NZ$328 per night
includes taxes & fees
Luxe Club RVA: Glam 2BR Escape
Living area
Exterior detail
Living area
Living area
Very good
(5 reviews)

East Clay Street Lofts Apt 1 - Convention Center

Richmond

19% off
NZ$5,477
for 7 nights, 1 apartment
NZ$782 per night
includes taxes & fees
East Clay Street Lofts Apt 1 - Convention Center
Room
Living area
Dining
Living area
Exceptional
(5 reviews)

Cozy & Chic Getaway - In The Heart Of RVA • 4BD 2.5BA • Sleeps 9+

Richmond

8% off
NZ$5,482
for 7 nights, 1 home
NZ$783 per night
includes taxes & fees
Cozy & Chic Getaway - In The Heart Of RVA • 4BD 2.5BA • Sleeps 9+
Interior
Dining
Private kitchen
Room
Exceptional
(18 reviews)

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

Petersburg

8% off
NZ$3,483
for 7 nights, 1 home
NZ$498 per night
includes taxes & fees
Nice! New home near VSU x Fort Lee Military Base mins to DT Richmond VA
Terrace/patio
Exterior detail
Exterior
Living area
Wonderful
(30 reviews)

Tropicana Bungalow - Retro Gem Near Fort Gregg-Adams and Old Towne

Petersburg

7% off
NZ$1,611
for 7 nights, 1 home
NZ$230 per night
includes taxes & fees
Tropicana Bungalow - Retro Gem Near Fort Gregg-Adams and Old Towne
Room
Classy dining perfect for two
Room
Enjoy the view of historic downtown Richmond
Exceptional
(14 reviews)

Jazzbird - Boutique Stay in Downtown RVA! Self Check-In and Free Wi-Fi!

Richmond

8% off
NZ$2,062
for 7 nights, 1 apartment
NZ$295 per night
includes taxes & fees
Jazzbird - Boutique Stay in Downtown RVA! Self Check-In and Free Wi-Fi!
Gorgeous art deco bedroom with full size mirror and lighted closet
Additional seating
Relax & unwind
Fully appointed kitchen
Exceptional
(7 reviews)

Charleston - Historic Downtown Richmond Retreat! Self Check-in, Wi-Fi, Extra Bed

Richmond

8% off
NZ$1,797
for 7 nights, 1 apartment
NZ$257 per night
includes taxes & fees
Charleston - Historic Downtown Richmond Retreat! Self Check-in, Wi-Fi, Extra Bed
Exterior
Private kitchen
Room
Dining
Exceptional
(20 reviews)

Luxe Cottage - South Chesterfield Stylishly renovated, w/ large master suite

Petersburg

7% off
NZ$3,092
for 7 nights, 1 home
NZ$442 per night
includes taxes & fees
Luxe Cottage - South Chesterfield Stylishly renovated, w/ large master suite
Interior
Room
Private kitchen
Living area
Exceptional
(13 reviews)

Private Guest house with Parking and Wi-Fi in a Central Location

Richmond

7% off
NZ$2,169
for 7 nights, 1 apartment
NZ$310 per night
includes taxes & fees
Private Guest house with Parking and Wi-Fi in a Central Location

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  • More quality time

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  • 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:

  • Pocahontas State Park (3.9 mi / 6.2 km)
  • Libby Hill Park (11.5 mi / 18.4 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 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:

  • 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)
  • Lewis Ginter Botanical Garden (17 mi / 27.4 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 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.
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.
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 Bookabach.
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.
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.
Are all fees included in the Chesterfield holiday homes prices shown on Bookabach?
Bookabach 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.
Are there any Chesterfield holiday homes with parking?
Bookabach offers a wide selection of holiday homes 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 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.
Are there any discounts for Chesterfield holiday homes?
You can find great discounts on holiday homes in Chesterfield on Bookabach, 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.
Can I change or cancel my Chesterfield holiday home booking on Bookabach?
To find Chesterfield holiday rentals with free cancellation, just use Bookabach'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". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Chesterfield?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach'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 favourites, and build the perfect itinerary together.
How early should I book a Chesterfield holiday home?
Book your Chesterfield holiday home 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 Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Chesterfield?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Chesterfield to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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.
Why should I join Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.