Photo by Nick Pagano

Chesterfield Holiday Rentals

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Holiday Rentals in Chesterfield

Magnolias, a chill out place.
10.0 out of 10, Exceptional, 7 reviews
"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 NZ$203
includes taxes & fees
26 Jun - 27 Jun
Magnolias, a chill out place.
Garden Penthouse in RVA! 3 Bedroom, 3 Bath!
10.0 out of 10, Exceptional, 9 reviews
"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!
Downtown Living in Historic Richmond Loft
8.4 out of 10, Very good, 41 reviews
"Wonderful apartment, plenty of room for us and located near many things to do!"
The price is NZ$523
includes taxes & fees
3 Jun - 4 Jun
Downtown Living in Historic Richmond Loft
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A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
9.6 out of 10, Exceptional, 191 reviews
"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 NZ$321
includes taxes & fees
18 Jun - 19 Jun
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
Lovely 2 Bedroom in the Heart of The Fan
9.4 out of 10, Exceptional, 35 reviews
"Super cute and roomy, hosts were super helpful and quick to respond! "
The price is NZ$494
includes taxes & fees
3 Jun - 4 Jun
Lovely 2 Bedroom in the Heart of The Fan
Cozy Get-A-Way in Neighborhood On 3 Lakes, With Fishing Docks, Firepit, Kayaks
9.8 out of 10, Exceptional, 9 reviews
"It was a beautiful small but roomy bungalow. Highly recommend!"
The price is NZ$677
includes taxes & fees
1 Jun - 2 Jun
Cozy Get-A-Way in Neighborhood On 3 Lakes, With Fishing Docks, Firepit, Kayaks
Great Location. Close to about everywhere .Can't beat the value. Check reviews!
10.0 out of 10, Exceptional, 170 reviews
"We needed a place to stay while in town for nephew’s graduation. This house was the perfect solution! Location was just 10 min from the family we were visiting and less than 5 min to grocery and coffee. Very sweet older neighborhood. Very convenient and cozy home."
Great Location. Close to about everywhere .Can't beat the value. Check reviews!
Brand New, Gorgeous Studio Close to Everything!
10.0 out of 10, Exceptional, 25 reviews
"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!
Modern, Lovely and Spacious Home
10.0 out of 10, Exceptional, 9 reviews
"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
Modern Unit in Historic Old Manchester.
10.0 out of 10, Exceptional, 25 reviews
"Mother’s Day weekend get away was definitely enhanced by the comfy environment which had every thing we needed! Property Manager initiated communications at all the right times. Lovely neighborhood with many opportunities to meet folks as they walk their fur-babies under tree-lined side-walks."
Modern Unit in Historic Old Manchester.
Central location w/ large fenced yard FIRE-PIT
10.0 out of 10, Exceptional, 22 reviews
"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 NZ$652
includes taxes & fees
18 Jun - 19 Jun
Central location w/ large fenced yard FIRE-PIT
Industrial Chic Loft in the Heart of Downtown Richmond!
9.8 out of 10, Exceptional, 7 reviews
"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!
The Bike Path House! Cozy 2 BR w/ Fireplace
9.4 out of 10, Exceptional, 9 reviews
"We loved the central location & proximity to the Bike Path. Very clean & cozy."
The Bike Path House! Cozy 2 BR w/ Fireplace
The Cozy Rancher | Petersburg | King Bed
10.0 out of 10, Exceptional, 21 reviews
"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 NZ$599
includes taxes & fees
2 Jun - 3 Jun
The Cozy Rancher | Petersburg | King Bed
Richmond Home w/ Fire Pit - 12 Mi to Downtown
10.0 out of 10, Exceptional, 9 reviews
"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
The lake house at lake chesdin
10.0 out of 10, Exceptional, 3 reviews
"Older home but well maintained. View of the lake was gorgeous, especially with the setting sun. Thanks!"
The price is NZ$800
includes taxes & fees
2 Jun - 3 Jun
The lake house at lake chesdin
Newly Renovated Historic Home < 2 Mi to Downtown!
9.8 out of 10, Exceptional, 47 reviews
"Enjoyed our time"
Newly Renovated Historic Home < 2 Mi to Downtown!
Terre Haute Manor Farmhouse w/ Gardens & Deck!
10.0 out of 10, Exceptional, 19 reviews
"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!
Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!
10.0 out of 10, Exceptional, 43 reviews
"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!
Idlewood Hive, the Heart of Richmond
9.8 out of 10, Exceptional, 34 reviews
"We had 3 generations under one roof for the VCU graduation. This home was close to campus, stores and restaurants. We had other family join us at the house to hang out together. The kitchen was a perfect spot for us all, the 2nd floor porch was great for views of the city. We had a great time staying there while we were in Richmond."
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

Drury Plaza Hotel Richmond
3.0 star property
9.6 out of 10, Exceptional, 2,321 reviews
"Excellent "
The price is NZ$240
includes taxes & fees
5 Jun - 6 Jun
Drury Plaza Hotel Richmond
Graduate Richmond
4.0 star property
8.4 out of 10, Very good, 1,128 reviews
"If I stated everything I loved about the property I’d be here forever, only negatives I have are the toilet in my room was leaking when I got there, which was fixed asap but then it would continuously try to fill the tank with water and I’d have to manually drop the lid after each use. 2 I never got a WiFi password and the cable signal was poor, with and without the storm. Minor inconveniences, excellent service of I go anywhere else with a graduate in town I will be staying there "
The price is NZ$302
includes taxes & fees
16 Jun - 17 Jun
Graduate Richmond
Omni Richmond Hotel
4.0 star property
8.8 out of 10, Excellent, 1,153 reviews
"Best shower, bed and hvac of our four hotel journey. Very comfortable one-night experience. We'll return."
The price is NZ$297
includes taxes & fees
16 Jun - 17 Jun
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Chesterfield holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Chesterfield. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Chesterfield. Seeing all the best attractions is bound to make you fall in love with Chesterfield. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Chesterfield short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Chesterfield?

Yes, there are holiday rentals close to the most popular sights in Chesterfield, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Chesterfield has to offer?

Cozy Get-A-Way in Neighborhood On 3 Lakes, With Fishing Docks, Firepit, Kayaks: This holiday home rental outside Chesterfield offers a fireplace, 1 hot tub and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Chesterfield?

Expedia has 8 holiday 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 holiday rentals like in Chesterfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesterfield. Holiday rentals offer extras such as patios, hot tubs and fire pits so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from shared hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for families.

Recent reviews of Chesterfield properties
Expedia verified reviews