Top 9 Airbnb Vacation Rentals In Chesterfield, Virginia - Updated 2024

Alexander
Alexander 
Updated
| 4 min read

Chesterfield Court House, also known as Chesterfield, Virginia, is a small, unincorporated community in the county seat of Chesterfield. The historic county courthouse complex called Chesterfield County Courthouse and Courthouse Square was listed on the National Register of Historic Places. This quaint town, as well as the surrounding county, has a long history that dates back to before the founding of the nation. Here, you get to soak up the views of the beautiful countryside in all directions. For accommodations, you can choose between a cute treehouse and a two-story family home. Check out our list of the top top 10 Airbnb vacation rentals in Chesterfield, Virginia.

We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 09, 2024.

1. Charming room on an alpaca farm (from USD 98)

This charming room is equipped with a microwave, refrigerator, coffeemaker, a king-size bed with memory foam, a queen sofa bed, and a balcony for taking in the views of the farm. It’s a very quiet and safe neighborhood but still offers easy access to the nearby city at about 20 mi (32 km). The rental also features daily farm fresh eggs, alpaca yarn, soaps, and honey. It is within close proximity to restaurants and shops.

Stayed at this property?
Richmond, Virginia, United States
11.26 km (7.0 mi) from Rockwood Park
664 reviews   Superhost Wifi Available
Private room in farm stay 2 Beds 6 Guests 1 Bedroom 1 Bathroom

Accommodates: 6

Top guest reviews
Amenities & Room:
the king bed was super comfy and pull out couch was fine for the kids
fresh flowers on table nice touches
we went in the summer so it was hot and the air conditioning was delicious
the softest bed and pillows we’ve enjoyed in a long time
very charming room complete with books to read and games to play
Cleanliness:
the room was clean and cozy
the place was clean and very comfy
clean quiet lovely place to stay
everything was super clean
very relaxed clean and stylish
Host:
they were so friendly and welcoming
maria is such a gracious host
hosts are super friendly make sure to say hi to the goats
maria and her husband were very nice host
maria was a welcoming host & we felt very comfortable in her home
Location:
maria’s location was perfect for the holiday
a very cute place in a farm in the heart of richmond
the shop also has some really unique hand crafted gifts
i choose this special place for my daughter’s 10th birthday
accesible location for our richmond activities very comfortable space and wonderful animals
Read more reviews

Nearby vacation rentals

2. Family-friendly home with a game room

This 2200 sq ft (204-sq m) rental features a sitting room with a fireplace, a room with a 70-in (177-cm) smart TV and leather couch, a game room upstairs that features a 50-in (127-cm) flat-screen television, Chromecast, Xbox 360, and a comfortable couch. The rental is located just 30 minutes from Richmond and close to local restaurants and a couple of wedding venues. In addition, River City Sports Complex is just a few miles away.

Stayed at this property?
Midlothian, Virginia, United States
2.99 km (1.9 mi) from Rockwood Park
114 reviews   Superhost Wifi Available
Entire residential home 4 Beds 8 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
very comfortable and great amenities
‘‘tis home is clean and well appointed with comfortable furnishings and all the modern conveniences
we loved the huge fenced in yard and the spacious rooms
the house is super cute obviously has been renovated and the furniture is very comfortable
most importantly i loved the game room
Cleanliness:
house clean and spacious too
very clean and comfortable accommodations
very clean beds are super comfy
clean and roomy with quick communication from host
great place very clean and comfortable
Host:
the host were amazing and responded quickly
simple fix but a host like that is worth every penny
the owners responded extremely quickly to requests and check in/check out was super easy
the host was very responsive and was able to communicate with us
the owner communicated quickly and was very good to work with
Location:
close to richmond cute tucked away safe neighborhood
the location is great very close to many stores and restaurants
best place to stay near richmond close to shopping and entertainment
perfect location if you want to be near brandermill country club
nice quiet place in a great location
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3. Updated ranch house with a full front porch

This lovely and updated ranch house comes complete with a gas fireplace, stainless steel appliances, a fenced-in backyard, a large laundry room, a balcony, and a porch. The spacious kitchen is equipped with modern appliances to help you cook meals easily. The two guest rooms are warm and cozy with flat-screen televisions, plush carpet, and two double beds. Since it’s in a convenient location, you can easily check out shopping centers, restaurants, and more. Aside from that, another thing that you will love about this rental is its green yard that surrounds the property.

Stayed at this property?
Midlothian, Virginia, United States
3.52 km (2.2 mi) from Rockwood Park
12 reviews   Superhost Wifi Available
ENTIRE HOME 2 Beds 2 Guests 2 Bedrooms 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
very comfortable home with plenty of space and easy access to the area
Host:
home is pleasant and ashley was friendly
ashley and her mom were excellent hosts and we're very quick to answer my questions and concerns
ashley’s place was perfect and she was a great host we will definitely come back in the future
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4. Bright colonial house in North Chesterfield

This bright rental, which is located in North Chesterfield, offers eight guests a relaxing stay. On the first floor, there’s a master bedroom with Wi-Fi, a fireplace, and air-conditioning. On the second floor, there are three bedrooms, a nursery with a playpen and a rocking chair, and a bathroom. Outside, there’s a furnished garage and deck with a grill. This rental is also close to bars and restaurants, in case you don’t feel like cooking.

Stayed at this property?
North Chesterfield, Virginia, United States
2.44 km (1.6 mi) from Rockwood Park
7 reviews   Wifi Available
ENTIRE HOME 4 Beds 8 Guests 4 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Host:
what a fun place to stay it was very comfortable and communication with the host was excellent
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5. Spacious home with six bedrooms

This sprawling home, which is in an upscale section of Richmond, is great for family reunions or romantic getaways. It features six bedrooms, three full bathrooms, and seven beds. There is a cozy living room with ample seating, a large front and backyard, an elegant formal dining room, and a full kitchen with modern. For sleeping arrangements, you have the option to sleep in the master bedroom with a long dresser or in another suite with two queen beds. Planning to have a movie night? The living area comes with enough seating and flat-screen television. The rental is close to numerous dining and entertainment options.

Stayed at this property?
Chesterfield, Virginia, United States
5.33 km (3.4 mi) from Rockwood Park
184 reviews   Wifi Available
ENTIRE HOME 7 Beds 12 Guests 6 Bedrooms 3 Bathrooms

Accommodates: 12

Top guest reviews
Amenities & Room:
roomy - so much room really nice neighborhood
for the tvs not to work but i loved everything else
Cleanliness:
everything was clean and working properly
everything was clean and easy to find
great place to stay very clean and spacious
clean convenient highly recommended
not fancy but clean and comfortable
Host:
gail is a great host
gail thank you for being the superstar host that you are
wonderful home and host was very accommodating will stay again
excellent place and host
gail was a fantastic host and the house served our needs for the weekend
Location:
house located in a great area pretty close to everything
a comfortable and convenient location
good place to stay close to the airport
it's a great location too
great value great location good stay
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6. Cute room with an attached bath (from USD 47)

Close to shopping, entertainment, and restaurants, this private room comes with the renter’s choice of either king or twin bed. It features a treadmill, a small refrigerator, a microwave, 42-in (106-cm) television with Roku, and an arcade with more than 7,000 retro games. The room, which has a private entrance via a spiral staircase, is equipped with free Wi-Fi and an office workspace. All-out privacy is guaranteed as this rental is tucked in a quiet, upscale neighborhood.

Stayed at this property?
Chesterfield, Virginia, United States
3.25 km (2.1 mi) from Rockwood Park
72 reviews   Wifi Available
Entire guest suite 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the bed is very comfortable and can apparently be set up either as a king or a twin
Cleanliness:
it was clean quiet and convenient
nice host quaint clean and small room perfect for my trip
very cute place and it was very clean
we loved our stay at bruce’a place it was very clean and in a convenient location
Host:
he is truly kind
great stay very hospitable and respectful
Location:
the place was great the area was close to everything and it met every needs
bruce's place is a great place to stay in richmond
the best thing about the suite at bruce's place is its flexibility
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7. Cozy cottage with a full kitchen (from USD 64)

You never have to worry about homey comforts when you book this tastefully decorated cottage in Midlothian. Its room features a comfortable queen-size bed and a large walk-in closet. For cooking some hearty meals, feel free to use the full kitchen with a pantry. At night, relax in the living area that comes with new furniture and flat-screen television.

Stayed at this property?
Midlothian, Virginia, United States
3.47 km (2.2 mi) from Rockwood Park
8 reviews   Wifi Available
ENTIRE RENTAL UNIT 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Cleanliness:
clean and great for commuting to work
you can expect to enjoy this spacious clean apartment in a lovely quiet neighborhood
Host:
melanie is kind and attentive - if you need things she will answer you quickly
Location:
hidden gem in a great location
i could come and go easily with street or driveway parking
it is private quiet and perfect for those working/needing a longer stay in the area
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8. Stylish home near downtown Richmond (from USD 400)

Set in a quiet neighborhood, this bright and spacious house features a cozy living room with comfortable seating, flat-screen television, fireplace, and functional office space with a computer. It also has a spacious formal dining room and an open kitchen with modern appliances. The bedrooms include two queens and bunk beds for the kids. If you’re traveling with a young one, this abode also offers a nursery with a crib and a playroom. In terms of places to visit, Ukrops Park, Busch Gardens, and Richmond Zoo are just a short drive away.

Stayed at this property?
Chesterfield, Virginia, United States
4.64 km (2.9 mi) from Rockwood Park
15 reviews   Wifi Available
ENTIRE HOME 4 Beds 8 Guests 4 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
the air conditioning was really good as the heat was intense
plenty of room for everyone to spread out and everything nicely childproofed
Host:
the hosts are kind and generous
this place is amazing cleaning hospitality is amazing spacious stylish and gracious host
nicely baby proofed and kid friendly
great kids space for my toddlers great outdoors space for the kids and adults; very very kid-friendly
Location:
the location is safe and the neighbors friendly
Read more reviews

9. Ranch-style house in a quaint neighborhood

This little apartment is ideal for a couple on a romantic getaway. It features one bedroom with a queen-sized bed, dresser, and closet. The living space is equipped with a couch and flat-screen TV, which is perfect for movie nights. You can also surprise your partner with a romantic dinner as the shared full-sized kitchen comes with anything else you might need.

Stayed at this property?
Chester, Virginia, United States
16.93 km (10.6 mi) from Rockwood Park
17 reviews  
Entire guest suite 1 Bed 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
the big screen tv was great for vegging on the weekends and the bed was really comfy
the kitchenette made life easy and her full kitchen was open for use right up the stairs
Cleanliness:
her place is very safe clean and stylish
comfy bed and sofa spotlessly clean
top notch air bnb great safe location and super clean and homey
Host:
the host was kind and responsive during my longer stay
rheshanna is an amazing host who was very welcoming toward me during my stay
rae is great host was kind enough to accept our last minute request and late checkin
Location:
i highly recommend this location
you have pretty close to a studio apartment to yourself
i abosolutely loved the neighbourhood
Read more reviews

10. Nice treehouse on a small farm

For your next vacation, why not try to stay in a treehouse? Located on a small farm, this cool space features a kitchen and coffee-making facilities. In terms of sleeping arrangements, it is advisable to ask the host for assistance. It’s set on a lush green property, where you can take a leisurely walk in the morning or stargaze at night. Guests also have access to a farm stand, gardens, and a campfire pit.

Stayed at this property?
Chesterfield, Virginia, United States
4.26 km (2.7 mi) from Rockwood Park
40 reviews  
Farm stay 0 Beds 0 Bathrooms
Top guest reviews
Amenities & Room:
the tree house was a perfect cozy getaway
the tree house itself was really neat and super cozy
Cleanliness:
cool space pretty much as advertised things were clean
such a unique property and had cooking and cleaning supplies would definitely stay here again
Host:
this place was great and the host was so quickly responsive
norm was a great host very kind and has a very cool place
norm was so quick to respond and kind to us during our visit
Location:
amazing location it was so cute to wake up to snow
the location is also great; can't beat a 20 minute drive to richmond
fun and unique place to stay at very close to downtown richmond as well so especially convenient
super cute quiet place to completely relax loved it
in relation to our trip the location was great
Read more reviews

Experience countryside living in Chesterfield

Surrounded by lush green fields, Chesterfield is a quaint town that provides tourists with easy access to larger cities such as Richmond and Petersburg. Whether you are in town for fun or business, be sure to check out our list of the top top 10 Airbnb vacation rentals in Chesterfield, Virginia.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Alexander is a veteran of the United States Navy, an editor-at-large, and a content writer/reviewer. He has written numerous opinion pieces, reality television articles, has taken a few interviews,...Read more

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