A traditional thatched-roof house with a sign reading 'Physick Garden' and a wooden fence.

Chesterfield County Vacation Rentals

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Our top choices for Chesterfield County vacation rentals

A wooden deck with a table and chairs, surrounded by potted plants and a wooden fence.

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

2. 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 $667 total
includes taxes & fees
Oct 22 - Oct 23
Qualla Park
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 $160
CA $392 total
includes taxes & fees
Oct 20 - Oct 21
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 $355
CA $786 total
includes taxes & fees
Oct 26 - Oct 27
Midlothian 3 Bedroom getaway for up to 8 guests!
A two-story house with a front porch and a small shed in a grassy yard.

5. Game Room + Yard: Updated House in Chester!

Game Room + Yard: Updated House in Chester!
3.0 star property
Chester
The price is CA $171
CA $492 total
includes taxes & fees
Oct 15 - Oct 16
Game Room + Yard: Updated House in Chester!
A living room with a sectional sofa, a flat-screen TV, a ceiling fan, and a modern chandelier.

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 $165
CA $427 total
includes taxes & fees
Oct 28 - Oct 29
Charming 1-bedroom suite with WiFi and AC in Bon Air
A spacious living area with a high ceiling, a staircase, and a dining area with modern furniture.

7. Game Room + Yard: Updated House in Chester!

Game Room + Yard: Updated House in Chester!
Chester
9.0 out of 10, Wonderful, (4 reviews)
"Great stay. Super clean! Great communication with host. 30 mins from Richmond VA, great for exploring surrounding areas!"
United States
Akia S.
The price is CA $119
CA $513 total
includes taxes & fees
Oct 15 - Oct 16
Game Room + Yard: Updated House in Chester!
A two-story house with a front deck, a small porch, and a backyard with a trampoline and a grill.

8. 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 16 - Oct 17
Private bedroom and bath!
A white building with a wooden porch, a red door, and a staircase leading to the entrance.

9. 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 $429
CA $1,017 total
includes taxes & fees
Oct 15 - Oct 16
Historic Vincent House - Luxury 5BR Retreat Near Richmond, Virginia - Sleeps 12
A modern kitchen with a central island, white cabinetry, and a large window with a view of greenery.

10. Serene 6-bedroom house with AC in charming Midlothian

Serene 6-bedroom house with AC in charming Midlothian
Brandermill
The price is CA $378
CA $952 total
includes taxes & fees
Oct 26 - Oct 27
Serene 6-bedroom house with AC in charming Midlothian
A bedroom with a large bed, a chandelier, a window with curtains, and a painting on the wall.

11. Boutique 4 BR Stay/ 3 Kings/ Backyard/ Fireplace

Boutique 4 BR Stay/ 3 Kings/ Backyard/ Fireplace
Chesterfield
The price is CA $438
CA $941 total
includes taxes & fees
Oct 18 - Oct 19
Boutique 4 BR Stay/ 3 Kings/ Backyard/ Fireplace
A calm lake with a dock and a small building, surrounded by trees.

12. 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 $303
CA $395 total
includes taxes & fees
Oct 17 - Oct 18
MV GiaMaria
A marina with docked boats, a covered structure, and a forested hillside in the background.

13. 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 CA $164
CA $307 total
includes taxes & fees
Oct 22 - Oct 23
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
A dock area with boats, a covered seating area, and a sign indicating no trespassing for boat owners and guests only.

14. 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 16 - Oct 17
Cookie B
A living room with two beige armchairs, a small table, and a black door.

15. 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 CA $170
CA $389 total
includes taxes & fees
Oct 18 - Oct 19
Cozy Bungalow | 3 Parking Spots | Fully Fenced Yard
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 a beige sofa, a round black coffee table, a large window, and a painting of a tree.

17. Charming 3-bedroom townhome with WiFi in delightful Richmond

Charming 3-bedroom townhome with WiFi in delightful Richmond
Jahnke
10.0 out of 10, Exceptional, (8 reviews)
"Check-in was simple, good communication, property very much as described/depicted in the listing. Perfect location for our needs. "
United States
Mary C.
The price is CA $283
CA $661 total
includes taxes & fees
Oct 20 - Oct 21
Charming 3-bedroom townhome with WiFi in delightful Richmond
A living room with a sofa, coffee table, TV, and a door with a 'No Smoking' sign.

18. 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
Nov 11 - Nov 12
The Birdhouse - Cozy Cottage Retreat in Richmond
A house with a covered porch, outdoor seating, and a well-lit deck area.

19. 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 $412 total
includes taxes & fees
Oct 26 - Oct 27
Steel Magnolias Cozy Main Home in Amelia County
A bedroom with a bed, a wooden nightstand, a desk, and a shelving unit.

20. Private Guest house with Parking and Wi-Fi in a Central Location

Private Guest house with Parking and Wi-Fi in a Central Location
Virginia Union
9.8 out of 10, Exceptional, (13 reviews)
"Amazing space. Great response time, our host was super friendly & helpful. The house was everything we were looking for and more, it was beautiful and the location was very convenient! "
United States
Michelle S.
The price is CA $106
CA $343 total
includes taxes & fees
Oct 20 - Oct 21
Private Guest house with Parking and Wi-Fi in a Central Location
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

Linden Row Inn

Linden Row Inn

10/10 Excellent
"Great historic property!"
Kimberley 1-night trip
Posted 12 hours ago
Linden Row Inn

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 $253 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.