Vacation Rentals in Chesterfield County

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Top cities in Chesterfield County

Check prices for these dates

Our top choices for Chesterfield County vacation rentals

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.
$200 nightly
The price is $230
Nov 21 - Nov 22
Total with taxes and fees
Newly finished basement suite in Midlothian. Very clean and spacious.

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

Game Room + Yard: Updated House in Chester!
3.0 star property
Chester
Game Room + Yard: Updated House in Chester!

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)
"The location is beautiful! Kristina was very prompt in answering my questions and very accommodating. Wonderful stay."
United States
Connie D.
$230 nightly
The price is $264
Nov 16 - Nov 17
Total with taxes and fees
Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.

4. 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.
$194 nightly
The price is $223
Nov 16 - Nov 17
Total with taxes and fees
Private bedroom and bath!

5. Qualla Park

Qualla Park
Chesterfield County
10.0 out of 10, Exceptional, (7 reviews)
"The home was beautiful and amazing! Host was amazing too! Highly recommend!"
United Kingdom
Shannon W.
$434 nightly
The price is $438
Nov 16 - Nov 17
Total with taxes and fees
Qualla Park

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.
$227 nightly
The price is $262
Nov 30 - Dec 1
Total with taxes and fees
Charming 1-bedroom suite with WiFi and AC in Bon Air

7. Close to Fort Gregg-Adams, VSU & Southside Medical – Comfort & Convenience

Close to Fort Gregg-Adams, VSU & Southside Medical – Comfort & Convenience
Petersburg
9.0 out of 10, Wonderful, (6 reviews)
"Big yard."
United States
Michael O.
$369 nightly
The price is $425
Nov 21 - Nov 22
Total with taxes and fees
Close to Fort Gregg-Adams, VSU & Southside Medical – Comfort & Convenience

8. 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, (25 reviews)
"Great host and close to everything!"
United States
Brian V.
$455 nightly
The price is $524
Nov 16 - Nov 17
Total with taxes and fees
Midlothian 3 Bedroom getaway for up to 8 guests!

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

Serene 6-bedroom house with AC in charming Midlothian
Brandermill
$745 nightly
The price is $858
Nov 17 - Nov 18
Total with taxes and fees
Serene 6-bedroom house with AC in charming Midlothian

10. 2 Full Beds|Non-Smoking

2 Full Beds|Non-Smoking
Petersburg VA
10.0 out of 10, Exceptional, (81 reviews)
"Appreciated the cozy lounge area, made relaxing after a long day easy."
United States
Anonymous traveler
$53 nightly
The price is $60
Nov 16 - Nov 17
Total with taxes and fees
2 Full Beds|Non-Smoking

11. 2 Full Bed|Smoking|Petersburg VA

2 Full Bed|Smoking|Petersburg VA
Petersburg VA
10.0 out of 10, Exceptional, (81 reviews)
"Cozy spot with friendly staff."
United States
Anonymous traveler
$53 nightly
The price is $60
Nov 16 - Nov 17
Total with taxes and fees
2 Full Bed|Smoking|Petersburg VA

12. Magnolias, a chill out place.

Magnolias, a chill out place.
Richmond
9.2 out of 10, Wonderful, (25 reviews)
"Would stay again!"
United States
Amir D.
$88 nightly
The price is $100
Nov 16 - Nov 17
Total with taxes and fees
Magnolias, a chill out place.

13. 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.
$138 nightly
The price is $154
Nov 29 - Nov 30
Total with taxes and fees
Nest & Rest | Private Studio | Free Parking

14. 2 Queen Beds | Non-Smoking, Micfridge

2 Queen Beds | Non-Smoking, Micfridge
Petersburg VA
10.0 out of 10, Exceptional, (4 reviews)
"Clean rooms with quick service!"
United States
Anonymous traveler
$68 nightly
The price is $75
Nov 16 - Nov 17
Total with taxes and fees
2 Queen Beds | Non-Smoking, Micfridge

15. MV GiaMaria

MV GiaMaria
3.5 star property
Richmond
9.4 out of 10, Exceptional, (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
$243 nightly
The price is $277
Nov 16 - Nov 17
Total with taxes and fees
MV GiaMaria

16. 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 BirdHouse is such a comfortable place. We loved the uniqueness and the little touches that mean alot on the road. We hope to stay again sometime."
United States
paula S.
$196 nightly
The price is $198
Nov 25 - Nov 26
Total with taxes and fees
The Birdhouse - Cozy Cottage Retreat in Richmond

17. Heart of RVA Arts District Walk to VCU, MCV, The National, Quirk Prime Downtown

Heart of RVA Arts District Walk to VCU, MCV, The National, Quirk Prime Downtown
Downtown Richmond
9.6 out of 10, Exceptional, (27 reviews)
"Great location, reasonable rates for the area, friendly helpful staff. Would stay here again."
United States
George L.
$138 nightly
The price is $158
Nov 16 - Nov 17
Total with taxes and fees
Heart of RVA Arts District Walk to VCU, MCV, The National, Quirk Prime Downtown

18. 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, (253 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.
$179 nightly
The price is $205
Nov 17 - Nov 18
Total with taxes and fees
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city

19. Cozy studio apartment in tranquil Richmond with heat and gym access

Cozy studio apartment in tranquil Richmond with heat and gym access
Downtown Richmond
8.8 out of 10, Excellent, (9 reviews)
"Clean environment. Great views. Very little parking flexibility but an enjoyable walk."
United States
Cailyn
$71 nightly
The price is $81
Nov 23 - Nov 24
Total with taxes and fees
Cozy studio apartment in tranquil Richmond with heat and gym access

20. New Heart of the Arts District Condo Downtown near MCV VCU Convention Center

New Heart of the Arts District Condo Downtown near MCV VCU Convention Center
Downtown Richmond
9.6 out of 10, Exceptional, (19 reviews)
"Clean, great location, and check-in and check-out were very easy!"
United States
Claire N.
New Heart of the Arts District Condo Downtown near MCV VCU Convention Center
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.

Find vacation rentals that suit your style

Top Chesterfield County Hotel Reviews

Frequently Asked Questions

How many vacation rentals are available in Chesterfield County?

Expedia has plenty of vacation rentals to choose from in and around Chesterfield County, so you’re guaranteed to find the right one for you.


How much is a vacation rental in Chesterfield County?

The selection of Chesterfield County vacation rentals we have selected for you start as low as $60 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Chesterfield County?

Vacation rentals in Chesterfield County come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Chesterfield County vacation rentals to suit everyone.


Why should I choose a vacation rental in Chesterfield County?

Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. 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.


How do I find the best deal on a vacation rental in Chesterfield County?

Find vacation rentals in Chesterfield County by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Chesterfield County.


What amenities are available in a vacation rental in Chesterfield County?

The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Chesterfield County vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Chesterfield County?

Everytime is a great time to head to Chesterfield County! Staying in a Chesterfield County vacation rentals you will always find lots going on to keep you entertained.


Why book a vacation rental with Expedia?

Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Chesterfield County. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Chesterfield County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Chesterfield County, you can save even more.


Can I cancel my vacation rental through Expedia?

Yes, you can cancel or change your Chesterfield County vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.


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