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

Chesterfield County Vacation Rentals

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Our top choices for Chesterfield County vacation 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 CA $288
CA $664 total
includes taxes & fees
Oct 12 - Oct 13
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 CA $141
CA $322 total
includes taxes & fees
Oct 26 - Oct 27
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 CA $134
CA $361 total
includes taxes & fees
Oct 12 - Oct 13
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 CA $356
CA $778 total
includes taxes & fees
Oct 5 - Oct 6
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 CA $185
CA $332 total
includes taxes & fees
Oct 24 - Oct 25
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 CA $175
CA $459 total
includes taxes & fees
Oct 12 - Oct 13
Charming 1-bedroom suite with WiFi and AC in Bon Air
A modern kitchen with a stainless steel refrigerator, a microwave, and a built-in oven. There are bar stools and a large island with a sink.

7. Spacious 4-bedroom house in awesome Midlothian with AC

Spacious 4-bedroom house in awesome Midlothian with AC
Brandermill
6.0 out of 10, (7 reviews)
"The property was clean and newly remodeled. We enjoyed our stay. Thank you"
United States
Shari F.
The price is CA $356
CA $935 total
includes taxes & fees
Oct 12 - Oct 13
Spacious 4-bedroom house in awesome Midlothian with AC
A white building with a wooden porch, a red door, and a staircase leading to the entrance.

8. 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 CA $422
CA $1,023 total
includes taxes & fees
Oct 6 - Oct 7
Historic Vincent House - Luxury 5BR Retreat Near Richmond, Virginia - Sleeps 12
A calm lake with a dock and a small building, surrounded by trees.

9. 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 CA $304
CA $395 total
includes taxes & fees
Oct 24 - Oct 25
MV GiaMaria
A dock area with boats, a covered seating area, and a sign indicating no trespassing for boat owners and guests only.

10. 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 CA $311
CA $426 total
includes taxes & fees
Oct 12 - Oct 13
Cookie B
A marina with docked boats, a covered structure, and a forested hillside in the background.

11. 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, (248 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 CA $164
CA $304 total
includes taxes & fees
Oct 12 - Oct 13
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
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, (124 reviews)
"Great alternative to a house or hotel"
United States
Ashley Jo P.
The price is CA $164
CA $304 total
includes taxes & fees
Oct 12 - Oct 13
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
A modern kitchen with a central island, stainless steel appliances, and bar stools.

13. 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)
"Very clean, cozy and in an excellent location."
United States
Courtney W.
The price is CA $211
CA $274 total
includes taxes & fees
Oct 12 - Oct 13
The Studio@ Eanes Drug-Heart of the Historic District
A living room with a sofa, coffee table, TV, and a door with a 'No Smoking' sign.

14. 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 CA $142
CA $295 total
includes taxes & fees
Oct 19 - Oct 20
The Birdhouse - Cozy Cottage Retreat in Richmond
A modern kitchen with white cabinetry, a stainless steel refrigerator, a built-in oven, and a microwave.

15. 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, (80 reviews)
"Nice stay"
United States
Danelle B.
The price is CA $237
CA $309 total
includes taxes & fees
Oct 11 - Oct 12
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.

16. 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 CA $105
CA $210 total
includes taxes & fees
Oct 20 - Oct 21
Nest & Rest | Private Studio | Free Parking
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, (10 reviews)
"The place was very nice and as advertised. Big backyard for your dog."
United States
Joseph
The price is CA $171
CA $387 total
includes taxes & fees
Oct 18 - Oct 19
Cozy Bungalow | 3 Parking Spots | Fully Fenced Yard
A house with a covered porch, outdoor seating, and a well-lit deck area.

18. 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 CA $220
CA $430 total
includes taxes & fees
Oct 12 - Oct 13
Steel Magnolias Cozy Main Home in Amelia County
IMG 6335

19. 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 price is CA $214
CA $276 total
includes taxes & fees
Oct 5 - Oct 6
The Enchanted Studio
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 CA $163
CA $512 total
includes taxes & fees
Oct 5 - Oct 6
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

Holiday Inn Express Richmond I-64 Short Pump Area by IHG

Holiday Inn Express Richmond I-64 Short Pump Area by IHG

10/10 Excellent
"Clean room and good staff"
Latrisha 2-night trip
Posted 1 hour ago
Holiday Inn Express Richmond I-64 Short Pump Area by IHG

Find out more about Chesterfield County

Everything you need to know about Chesterfield County 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 County 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 County vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chesterfield County vacation 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 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 County vacation rentals we have selected for you start as low as CA $274 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 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 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 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 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.