Vacation Rentals in Chesterfield County

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Top Cities in Chesterfield County

Our top choices for Chesterfield County vacation rentals

10.0 out of 10, Exceptional, (1)
"Great spot to spend the evening while traveling through! Comfortable space.Host was very helpful through the check in process and my stay.Thanks Pamela!"
United States
Shawn P.
$142 nightly
The price is $163
Jan 5 - Jan 6, 2026
Total with taxes and fees
Newly finished basement suite in Midlothian. Very clean and spacious.
10.0 out of 10, Exceptional, (8)
"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.
$254 nightly
The price is $292
Jan 13 - Jan 14, 2026
Total with taxes and fees
Charming 1-bedroom suite with WiFi and AC in Bon Air
10.0 out of 10, Exceptional, (4)
"Visiting friends "
United States
Todd K.
$235 nightly
The price is $270
Jan 1 - Jan 2, 2026
Total with taxes and fees
Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.
8.0 out of 10, Very Good, (4)
"The rental process was easy. The property was very clean. I will definitely rent again next time we are in town to visit family."
United States
Shelia C.
$176 nightly
The price is $203
Jan 12 - Jan 13, 2026
Total with taxes and fees
Luxe King Bd W Resort Amenities
9.6 out of 10, Exceptional, (18)
"Beautiful condo very well furnished. Great location."
United States
Sue P.
$451 nightly
The price is $519
Dec 30 - Dec 31
Total with taxes and fees
Midlothian 3 Bedroom getaway for up to 8 guests!

Vacation Home in Midlothian

Private bedroom and bath!
10.0 out of 10, Exceptional, (1)
"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.
$202 nightly
The price is $233
Dec 30 - Dec 31
Total with taxes and fees
Private bedroom and bath!
2.0 star property
2.0 out of 10, (2)
"We did not end up staying there. The listing was for the entire home. When we arrived, a white vehicle was parked in the driveway. When we went in, the foyer was not picked up-see photo. The kitchen was not usable because the countertop contained dirty dishes, 3 ears of freshly cooked corn, and a large helping of shredded meat-see photo. There was a small pile of shredded meat beside the stove-see photo. The sink was full of unwashed pots and pans-see photo. Also, the listing was for two...
United States
Theresa H.
$68 nightly
The price is $78
Jan 4 - Jan 5, 2026
Total with taxes and fees
PRIVATE 2 BEDROOM w/ BATH/SHOWER COMBO - Chesterfield, VA

Houseboat in Richmond

Cookie B
3.0 star property
9.6 out of 10, Exceptional, (7)
"Was fantastic. Watching the sunrise was so memorable, captain ron was so friendly and stayed in communication well. will visit again. "
United States
Reshelle
$164 nightly
The price is $187
Jan 1 - Jan 2, 2026
Total with taxes and fees
Cookie B

Houseboat in Richmond

MV GiaMaria
3.5 star property
9.2 out of 10, Wonderful, (16)
"We liked the coziness of the boat, the views of the river, the surrounding areas were beautiful. The only negative thing we could say was that due to the ran/wind the boat creaked and it made it hard to sleep for one of our nights."
United States
warren
$156 nightly
The price is $178
Jan 12 - Jan 13, 2026
Total with taxes and fees
MV GiaMaria
9.6 out of 10, Exceptional, (113)
"2nd time staying at this property and definitely won’t be the last! Amazing location and great host."
United States
Alexis S.
$186 nightly
The price is $213
Dec 31 - Jan 1, 2026
Total with taxes and fees
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
10.0 out of 10, Exceptional, (10)
"House was amazing and host was very kind and helpful"
United States
Aaron R.
$143 nightly
The price is $154
Jan 6 - Jan 7, 2026
Total with taxes and fees
Charming 2-bedroom home, with lake access, in the Richmond metro area.

Apartment in Richmond

Magnolias, a chill out place.
9.4 out of 10, Exceptional, (20)
"Enjoyed my stay a lot! The property definitely has charm, the experience was very laid back. "
United States
Grace
$104 nightly
The price is $119
Jan 12 - Jan 13, 2026
Total with taxes and fees
Magnolias, a chill out place.
10.0 out of 10, Exceptional, (38)
"It was a great stay."
United States
Manuela G.
$123 nightly
The price is $136
Jan 1 - Jan 2, 2026
Total with taxes and fees
Cozy nest/private porch/museums/free parking
10.0 out of 10, Exceptional, (4)
"Amazing Stay. Very helpful & has everything you need . We will be coming back soon . Thank You James ! "
United Kingdom
Travis K.
$380 nightly
The price is $407
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Vibe: 3BR- Wedding-Ready Retreat with King Comfort & Fire Pit on 10 acres
9.4 out of 10, Exceptional, (228)
"Beautiful setting and comfortable accommodations. "
United States
deirdre b.
$185 nightly
The price is $211
Jan 6 - Jan 7, 2026
Total with taxes and fees
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city

Apartment in Church Hill

The Studio@ Eanes Drug
10.0 out of 10, Exceptional, (54)
"Great property! Perfect for what we needed!"
United States
Rob P.
$135 nightly
The price is $154
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Studio@ Eanes Drug
8.6 out of 10, Excellent, (31)
"Was I great place to stay! Very responsive and gave all the info you need to make the trip and stay easy! "
United States
Dillon D.
$208 nightly
The price is $222
Dec 30 - Dec 31
Total with taxes and fees
Downtown Living in Richmond's Amazing Shockoe Bottom

Apartment in Church Hill

Historic Haven in Church Hill
10.0 out of 10, Exceptional, (46)
"Great place, great location!"
United States
Janet F.
$145 nightly
The price is $166
Dec 30 - Dec 31
Total with taxes and fees
Historic Haven in Church Hill

Vacation Home in Southern Barton Heights

Charming Getaway in the Heart of RVA-No Cleaning Fee
10.0 out of 10, Exceptional, (2)
"House was perfect. "
United States
Sovi T.
$536 nightly
The price is $613
Dec 30 - Dec 31
Total with taxes and fees
Charming Getaway in the Heart of RVA-No Cleaning Fee
2.0 star property
10.0 out of 10, Exceptional, (2)
"Check-in was simple and the space was perfect for my family."
United States
Eric B.
$218 nightly
The price is $249
Jan 26 - Jan 27, 2026
Total with taxes and fees
Farmhouse Boho Retreat Peaceful 2 BR w/ Porch and Fenced Backyard
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chesterfield County Hotel Reviews

Find out more about Chesterfield County

Discover your perfect Chesterfield County vacation rental with Expedia

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 $78 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.