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Chesterfield Vacation Rentals

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Vacation Rentals in Chesterfield

Exterior
Magnolias, a chill out place.
10.0 out of 10, Exceptional, (7)
"Magnolias is exactly what it is advertising. A great place to stay for a few nights when visiting RVA. Super close to the RIC. Easy to get to and from downtown. Very comfortable. Well worth the price."
The price is ¥10,832
¥19,507 total
includes taxes & fees
Jun 3 - Jun 4
Magnolias, a chill out place.
Fridge, microwave, oven, stovetop
Garden Penthouse in RVA! 3 Bedroom, 3 Bath!
10.0 out of 10, Exceptional, (9)
"This is the place for you and yours! We came to Richmond to see the sites and tour civil war era places. It was always so nice to come "home""
Garden Penthouse in RVA! 3 Bedroom, 3 Bath!
Fridge, microwave, oven, stovetop
Downtown Living in Historic Richmond Loft
8.4 out of 10, Very Good, (41)
"Wonderful apartment, plenty of room for us and located near many things to do!"
The price is ¥24,561
¥50,212 total
includes taxes & fees
May 28 - May 29
Downtown Living in Historic Richmond Loft
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Property grounds
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
9.6 out of 10, Exceptional, (191)
"We had an enjoyable stay on the houseboat. The bed was comfortable, and the accommodations had everything we needed. We even made spaghetti the first night for dinner since we arrived later than planned. The area is private, we only saw a few people and those we did see gave a friendly hello if they didn't stop to chat with us. For anyone wondering about the movement of the boat, it is very stable. The boat is docked in a channel off the main river so not a lot of boat traffic and the currents...
The price is ¥15,699
¥30,783 total
includes taxes & fees
May 29 - May 30
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
Fridge, microwave, oven, stovetop
Lovely 2 Bedroom in the Heart of The Fan
9.4 out of 10, Exceptional, (35)
"We really liked our apartment. It was clean and comfortable and the location was perfect. There were only 2 issues. The water pressure in the bathroom was extremely low. And the neighbor upstairs was SO loud. They had loud conversations until around 2 AM, heavy footsteps, and an extremely loud TV that stayed on all night until 4 AM. It was almost impossible to sleep."
The price is ¥24,561
¥47,401 total
includes taxes & fees
May 29 - May 30
Lovely 2 Bedroom in the Heart of The Fan
Property grounds
Cozy Get-A-Way in Neighborhood On 3 Lakes, With Fishing Docks, Firepit, Kayaks
9.8 out of 10, Exceptional, (9)
"A group of friends from church and I stayed here to attend a marriage retreat at Passion Commmunity Church in Powhatan. We had the best time and the location was perfect for an overnight with multiple couples."
The price is ¥31,241
¥65,000 total
includes taxes & fees
May 28 - May 29
Cozy Get-A-Way in Neighborhood On 3 Lakes, With Fishing Docks, Firepit, Kayaks
Property grounds
Great Location. Close to about everywhere .Can't beat the value. Check reviews!
10.0 out of 10, Exceptional, (169)
"Quickly felt like “home” for dog and people! Comfortable location with easy access to restaurants and stores. Will definitely stay here again when visiting Richmond!"
Great Location. Close to about everywhere .Can't beat the value. Check reviews!
Private kitchen | Fridge, microwave, oven, stovetop
Brand New, Gorgeous Studio Close to Everything!
10.0 out of 10, Exceptional, (25)
"Cleanliness was outstanding; we appreciated the thoughtfulness of the water bottles and the wine; excellent soap/hair products; very appealing decor; the bed was very comfortable, especially when we used the additional mattress pad. One wrinkle for us was the challenge of pulling out the sofa to bed conversion. Once we did that and added the padding from the closet, sleeping was great. We were so impressed with how you utilized the space and how you thought of everything we could want. Also,...
Brand New, Gorgeous Studio Close to Everything!
Exterior
Modern, Lovely and Spacious Home
10.0 out of 10, Exceptional, (9)
"This is a lovely home with the charm of years gone by and located in historic Jackson Ward. It is in easy walking distance from numerous restaurants, shops, and the contemporary art museum. The hostess was in regular communication with us to ensure we had a great stay."
Modern, Lovely and Spacious Home
Terrace/patio
Modern Unit in Historic Old Manchester.
10.0 out of 10, Exceptional, (22)
"We had a great time at this location. Close to everything and very clean. Had everything that we needed. Very comfortable beds. Made us feel like we were at home. Will definitely try to stay here next time in town."
Modern Unit in Historic Old Manchester.
Terrace/patio
Central location w/ large fenced yard FIRE-PIT
10.0 out of 10, Exceptional, (22)
"This was a wonderful home and a fantastic experience. The host was perfectly communicative, the check in process was simple and seamless. The house was clean and comfortable, stocked with everything we needed- including a functioning grill and a stockpile of wood for fires out back, which we had one every single night. We had four adults and three children, and there was plenty of space between the rooms. The beds were comfortable and having a large TV in the living room preset with streaming...
The price is ¥15,228
¥40,089 total
includes taxes & fees
May 28 - May 29
Central location w/ large fenced yard FIRE-PIT
Exterior
Industrial Chic Loft in the Heart of Downtown Richmond!
9.8 out of 10, Exceptional, (7)
"I loved it was so close to everything history this place was amazing and will be back in the future "
Industrial Chic Loft in the Heart of Downtown Richmond!
Property grounds
The Bike Path House! Cozy 2 BR w/ Fireplace
9.4 out of 10, Exceptional, (9)
"We loved the central location & proximity to the Bike Path. Very clean & cozy."
The Bike Path House! Cozy 2 BR w/ Fireplace
4 bedrooms, iron/ironing board, free WiFi, bed sheets
The Cozy Rancher | Petersburg | King Bed
10.0 out of 10, Exceptional, (21)
"We loved this property it was truly a home away from home. This house was clean, decorative, nice clean smell, and located in a quite neighborhood. It was truly relaxing and made us feel right at home."
The price is ¥22,764
¥55,570 total
includes taxes & fees
May 28 - May 29
The Cozy Rancher | Petersburg | King Bed
Fridge, microwave, stovetop, dishwasher
Richmond Home w/ Fire Pit - 12 Mi to Downtown
10.0 out of 10, Exceptional, (7)
"We had a wonderful stay at this property -- it was exactly as advertised. It was spotlessly clean, the beds were comfortable, it had all needed amenities, and it was in a great location. I highly recommend it."
Richmond Home w/ Fire Pit - 12 Mi to Downtown
Smart TV, fireplace
The lake house at lake chesdin
10.0 out of 10, Exceptional, (3)
"Older home but well maintained. View of the lake was gorgeous, especially with the setting sun. Thanks!"
The price is ¥46,940
¥65,634 total
includes taxes & fees
May 29 - May 30
The lake house at lake chesdin
Fridge, microwave, stovetop, dishwasher
Newly Renovated Historic Home < 2 Mi to Downtown!
9.8 out of 10, Exceptional, (46)
"It was perfect for the board members to stay together, away from the conference center, room to relax and solve the little problems that arise, away from the exhibition hall. Enough seating space for everyone involved for dinners and relaxation. Great for large group discussions and small group conversations."
Newly Renovated Historic Home < 2 Mi to Downtown!
Fridge, microwave, stovetop, dishwasher
Terre Haute Manor Farmhouse w/ Gardens & Deck!
10.0 out of 10, Exceptional, (19)
"I took two teams (UMASS & JMU) to the college super regional Pickleball tournament. The house was fantastic because it was affordable for college kids (though one needed to be 30 years of age to book it…I exceed that age), it had lots of beds and enough bathrooms and a kitchen. I recommend getting there in the daylight hours because it is a little off the beaten path and dark when you arrive but it was perfect fit for our needs - great hospitality! Beautiful animals in the property too (donkeys...
Terre Haute Manor Farmhouse w/ Gardens & Deck!
Interior
Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!
10.0 out of 10, Exceptional, (43)
"My husband and I stayed in Richmond for a long weekend and lucked onto this beautiful condo in downtown. We are fans of old buildings and this one was old but still in great shape, very nicely kept up and included all the amenities we needed. The condo had 3 huge street- facing windows that admitted Plenty of light and made for some fun watching of the street scene below. Check in was seamless and the hosts were super responsive. We had to keep moving our car around in order to obtain reasonable...
Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!
Private kitchen | Fridge, microwave, oven, stovetop
Idlewood Hive, the Heart of Richmond
9.8 out of 10, Exceptional, (34)
"Great location with tons of beds. Very convenient to the convention center and downtown. Thanks for having us!"
Idlewood Hive, the Heart of Richmond
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See all available properties in Chesterfield
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Chesterfield you may be interested in

Lobby
Drury Plaza Hotel Richmond
3.0 star property
9.6 out of 10, Exceptional, (2304)
"We discovetedcthis hotel chain on Arizona and susequently sought out the Drury Plaza in Richmond. It did not disappoint. Will definitely use Drury whenever we can in our travels."
The price is ¥19,779
¥23,000 total
includes taxes & fees
Jun 3 - Jun 4
Drury Plaza Hotel Richmond
Rooftop terrace
Graduate Richmond
4.0 star property
8.2 out of 10, Very Good, (1128)
"Great place "
The price is ¥24,961
¥29,026 total
includes taxes & fees
Jun 16 - Jun 17
Graduate Richmond
Exterior
Omni Richmond Hotel
4.0 star property
8.6 out of 10, Excellent, (1159)
"Front desk was amazing and the rooms were clean "
The price is ¥23,888
¥27,778 total
includes taxes & fees
Jun 16 - Jun 17
Omni Richmond Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Frequently asked questions

Can I find a vacation rental in Chesterfield?

Yes, we give you a choice of vacation rentals close to popular local attractions in Chesterfield, or you can choose a more secluded option if you're looking for relaxation. Chesterfield is known for its shopping and golf courses. Make sure you have time to check out the parks and museums during your trip.

What are some of the best vacation rentals that Chesterfield has to offer?

The Bike Path House! Cozy 2 BR w/ Fireplace: This vacation home rental outside of Chesterfield offers a fireplace, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You and your friends and family can relax into your vacation with amenities like a garden.

How many vacation rentals are there in Chesterfield?

Expedia has 8 vacation rentals for your stay in Chesterfield.

What can I see and do in Chesterfield?

Pocahontas State Park and Appomattox River are a couple of lovely local spots to get outside and enjoy nature. Castlewood and Pocahontas State Park Museum are other places to visit while you're in town.

What are vacation rentals like in Chesterfield?

Vacation rentals are privately owned properties you can stay in for a short or long stay in Chesterfield. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for a small group gathering.

Recent reviews of Chesterfield properties
Expedia verified reviews