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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 CA $94
CA $169 total
includes taxes & fees
Jun 25 - Jun 26
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 CA $213
CA $436 total
includes taxes & fees
May 29 - May 30
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 CA $136
CA $267 total
includes taxes & fees
Jun 12 - Jun 13
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 CA $213
CA $412 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 CA $271
CA $564 total
includes taxes & fees
Jun 2 - Jun 3
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
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, (23)
"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 CA $187
CA $420 total
includes taxes & fees
Jun 4 - Jun 5
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 CA $198
CA $483 total
includes taxes & fees
May 29 - May 30
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, (8)
"It was a perfect location, central to downtown and the west end of suburbs. Close to a hospital if needed, close to 64 and Broad street. Great bbq at Buzz and Ned’s. Very quiet neighborhood. Overall a great wedding weekend."
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 CA $409
CA $571 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, (47)
"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
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
Don't see what you're looking for?
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.

Chesterfield Vacation Rental Travel Info

Popular accommodation
Chesterfield private vacation homes
Known landmarks
Pocahontas State Park, Uptown Alley and Pocahontas State Park Museum
International airport
Richmond, VA (RIC-Richmond Intl.)

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, (2307)
"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 CA $172
CA $200 total
includes taxes & fees
Jun 2 - Jun 3
Drury Plaza Hotel Richmond
Rooftop terrace
Graduate Richmond
4.0 star property
8.2 out of 10, Very good, (1130)
"We enjoyed our stay and the vibe at the hotel is very cool. The bathroom was a little worn and we were disappointed that the bunkbeds weren’t made up with sheets (even though our kids were on the reservation), but all in all, it was a good stay."
The price is CA $217
CA $253 total
includes taxes & fees
Jun 16 - Jun 17
Graduate Richmond
Exterior
Omni Richmond Hotel
4.0 star property
8.6 out of 10, Excellent, (1161)
"Front desk was amazing and the rooms were clean "
The price is CA $207
CA $241 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.

Everything you need to know about Chesterfield vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterfield vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesterfield vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chesterfield vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterfield. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesterfield vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesterfield vacation rentals we have selected for you start as low as CA $94 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesterfield rentals

At Expedia, we put the best Chesterfield vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chesterfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesterfield vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesterfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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

Quirk Hotel Richmond

Quirk Hotel Richmond

5/5 Excellent
Love the Quirk
"Fabulous hotel. Love the room, coffee bar and art gallery on the first floor were perfect. "
A verified traveller stayed at Quirk Hotel Richmond
Posted 18 hours ago
Quirk Hotel Richmond