A pathway through tall grass with the sun setting in the background.

Chesterfield County Holiday Rentals

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Our top choices for Chesterfield County holiday rentals

A kitchen with a wooden island, stainless steel appliances, and a chandelier.

1. Qualla Park

Qualla Park
Chesterfield County
10.0 out of 10, Exceptional, (5 reviews)
"The home was beautiful and amazing! Host was amazing too! Highly recommend!"
United Kingdom
Shannon W.
The price is NZ$822
includes taxes & fees
12 Oct - 13 Oct
Qualla Park
A wooden deck with a table and chairs, surrounded by potted plants and a wooden fence.

2. Newly finished basement suite in Midlothian. Very clean and spacious.

Newly finished basement suite in Midlothian. Very clean and spacious.
Midlothian
10.0 out of 10, Exceptional, (6 reviews)
"Cute place. Very spacious and clean. Great communication. Would definitely stay again. Thank you!"
United States
Jeannie C.
The price is NZ$399
includes taxes & fees
26 Oct - 27 Oct
Newly finished basement suite in Midlothian. Very clean and spacious.
A rural landscape with a dirt path, grassy areas, and a building with a green roof.

3. Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.

Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.
Chesterfield
10.0 out of 10, Exceptional, (7 reviews)
"Quiet and Cozy. Beautiful scenery, great walking trails. Host was extra accomdating with check-in and out process. Would definitely visit again "
United States
G H.
The price is NZ$494
includes taxes & fees
12 Oct - 13 Oct
Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.
A modern kitchen with a central island, white cabinetry, and a dining area with a table and chairs.

4. Midlothian 3 Bedroom getaway for up to 8 guests!

Midlothian 3 Bedroom getaway for up to 8 guests!
Midlothian
9.6 out of 10, Exceptional, (24 reviews)
"Great host and close to everything!"
United States
Brian V.
The price is NZ$978
includes taxes & fees
12 Oct - 13 Oct
Midlothian 3 Bedroom getaway for up to 8 guests!
A two-story house with a front deck, a small porch, and a backyard with a trampoline and a grill.

5. Private bedroom and bath!

Private bedroom and bath!
Midlothian
6.0 out of 10, (2 reviews)
"We had a lacrosse tournament at River city sports plex. This was perfect location to stay for us. Friendly and amazing combination with host. Extremely pleased with our stay"
United States
Ridge W.
The price is NZ$415
includes taxes & fees
9 Oct - 10 Oct
Private bedroom and bath!
A modern living room with a grey sofa, a patterned rug, and a unique spherical light fixture.

6. Charming 1-bedroom suite with WiFi and AC in Bon Air

Charming 1-bedroom suite with WiFi and AC in Bon Air
Bon Air
8.8 out of 10, Excellent, (11 reviews)
"It was a nice stay the host was prompt and answered any questions or concerns right away, she was very polite and helpful to me and family "
United States
Jessica H.
The price is NZ$572
includes taxes & fees
9 Oct - 10 Oct
Charming 1-bedroom suite with WiFi and AC in Bon Air
A white building with a wooden porch, a red door, and a staircase leading to the entrance.

7. Historic Vincent House - Luxury 5BR Retreat Near Richmond, Virginia - Sleeps 12

Historic Vincent House - Luxury 5BR Retreat Near Richmond, Virginia - Sleeps 12
Midlothian
9.8 out of 10, Exceptional, (10 reviews)
"This vintage home was the perfect place for our stay. It was very clean, had everything we needed, and the location near the wedding venue couldn’t have been better."
United States
Sandy
The price is NZ$1,226
includes taxes & fees
21 Oct - 22 Oct
Historic Vincent House - Luxury 5BR Retreat Near Richmond, Virginia - Sleeps 12
A calm lake with a dock and a small building, surrounded by trees.

8. MV GiaMaria

MV GiaMaria
3.5 star property
Richmond
9.2 out of 10, Wonderful, (16 reviews)
"So much fun!! Excellent host! Very informative. Loved the privacy and being on the water. The bed was super comfortable and the fireplace (electric) kept us warm and cozy. It was such a unique thing to do and we will be back!"
United States
Jane
The price is NZ$496
includes taxes & fees
9 Oct - 10 Oct
MV GiaMaria
A dock area with boats, a covered seating area, and a sign indicating no trespassing for boat owners and guests only.

9. Cookie B

Cookie B
3.0 star property
Richmond
9.6 out of 10, Exceptional, (9 reviews)
"Was fantastic. Watching the sunrise was so memorable, captain ron was so friendly and stayed in communication well. will visit again. "
United States
Reshelle
The price is NZ$535
includes taxes & fees
9 Oct - 10 Oct
Cookie B
A marina with docked boats, a covered structure, and a forested hillside in the background.

10. A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city

A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
Richmond
9.4 out of 10, Exceptional, (249 reviews)
"We had a great stay! Perfect get away for our anniversary. It had everything we needed and was super quiet with a great view. Thank you Captain Ron, for an amazing experience "
United States
Allison K.
The price is NZ$380
includes taxes & fees
12 Oct - 13 Oct
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
A house with a covered porch, outdoor seating, and a well-lit deck area.

11. Steel Magnolias Cozy Main Home in Amelia County

Steel Magnolias Cozy Main Home in Amelia County
Amelia Court House
9.6 out of 10, Exceptional, (15 reviews)
"I would highly recommend Jenny’s VRBO- the house was beautiful, clean, and she was incredibly welcoming and communicative! "
United States
Marissa H.
The price is NZ$540
includes taxes & fees
12 Oct - 13 Oct
Steel Magnolias Cozy Main Home in Amelia County
A grand lobby with a large Christmas tree, marble columns, and a red carpeted floor.

12. A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations

A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
Richmond
9.6 out of 10, Exceptional, (125 reviews)
"Great alternative to a house or hotel"
United States
Ashley Jo P.
The price is NZ$378
includes taxes & fees
11 Oct - 12 Oct
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
A living room with a sofa, coffee table, TV, and a door with a 'No Smoking' sign.

13. The Birdhouse - Cozy Cottage Retreat in Richmond

The Birdhouse - Cozy Cottage Retreat in Richmond
Swansboro West
10.0 out of 10, Exceptional, (6 reviews)
"The most beautifully finished cottage! Host very responsive!! Loved it."
United States
Stephanie S.
The price is NZ$364
includes taxes & fees
18 Oct - 19 Oct
The Birdhouse - Cozy Cottage Retreat in Richmond
A modern kitchen with white cabinetry, a stainless steel refrigerator, a built-in oven, and a microwave.

14. Historic Haven in Church Hill in The Heart of the Historic District

Historic Haven in Church Hill in The Heart of the Historic District
Church Hill
10.0 out of 10, Exceptional, (83 reviews)
"Nice stay"
United States
Danelle B.
The price is NZ$381
includes taxes & fees
11 Oct - 12 Oct
Historic Haven in Church Hill in The Heart of the Historic District
A room with a fireplace, a mirror above it, and two leather chairs.

15. Nest & Rest | Private Studio | Free Parking

Nest & Rest | Private Studio | Free Parking
Fan District
9.8 out of 10, Exceptional, (46 reviews)
"Host was gracious and responsive, and the location was amazing! "
United States
Kelly M.
The price is NZ$264
includes taxes & fees
20 Oct - 21 Oct
Nest & Rest | Private Studio | Free Parking
A modern kitchen with a central island, stainless steel appliances, and bar stools.

16. The Studio@ Eanes Drug-Heart of the Historic District

The Studio@ Eanes Drug-Heart of the Historic District
Church Hill
10.0 out of 10, Exceptional, (101 reviews)
"Great spot. Second time staying and another excellent experience."
United States
Nello D.
The price is NZ$346
includes taxes & fees
14 Oct - 15 Oct
The Studio@ Eanes Drug-Heart of the Historic District
A living room with two beige armchairs, a small table, and a black door.

17. Cozy Bungalow | 3 Parking Spots | Fully Fenced Yard

Cozy Bungalow | 3 Parking Spots | Fully Fenced Yard
Richmond
10.0 out of 10, Exceptional, (12 reviews)
"The place was very nice and as advertised. Big backyard for your dog."
United States
Joseph
The price is NZ$485
includes taxes & fees
15 Oct - 16 Oct
Cozy Bungalow | 3 Parking Spots | Fully Fenced Yard
IMG 6335

18. The Enchanted Studio

The Enchanted Studio
Huguenot
10.0 out of 10, Exceptional, (2 reviews)
"This was the most relaxing and peaceful visit.Nature all around and the most comfortable accommodations.So grateful to my generous host. Thank you!!"
United States
Mary B.
The Enchanted Studio
A modern kitchen with dark cabinets, a large island, stainless steel appliances, and a hanging light fixture.

19. Hike, Golf & Explore! Peaceful Home in Montpelier

Hike, Golf & Explore! Peaceful Home in Montpelier
3.0 star property
Montpelier
The price is NZ$505
includes taxes & fees
20 Oct - 21 Oct
Hike, Golf & Explore! Peaceful Home in Montpelier
A modern living room with a teal sofa, a coffee table, and a TV on a stand. There is a 'WELCOME' sign on the wall and a framed picture above the sofa.

20. Lovely 2 Bedroom in the Heart of The Fan

Lovely 2 Bedroom in the Heart of The Fan
Fan District
9.2 out of 10, Wonderful, (88 reviews)
"Great location and very walkable to restaurants, shopping and museums."
United States
Nancy D.
The price is NZ$620
includes taxes & fees
21 Oct - 22 Oct
Lovely 2 Bedroom in the Heart of The Fan
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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Top Chesterfield County Hotel Reviews

Comfort Suites At Virginia Center Commons

Comfort Suites At Virginia Center Commons

10/10 Excellent
"Great value for the price."
Angela 2-night trip
Posted 1 hour ago
Comfort Suites At Virginia Center Commons

Find out more about Chesterfield County

Everything you need to know about Chesterfield County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterfield County holiday rental for you. At Expedia, you can take your pick from private holiday 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 County holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chesterfield County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterfield County. 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 County holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesterfield County holiday rentals we have selected for you start as low as NZ$346 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesterfield County rentals

At Expedia, we put the best Chesterfield County holiday 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 County 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 County holiday.

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 County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.