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Find Vacation Homes in Chesterfield County, VA from $259

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Top Cities in Chesterfield County

Vacation Homes in Chesterfield County

Stylish retreat in charming Richmond with Private Sauna and other modern touches

Swansboro
9.8 out of 10, Exceptional, (19)
"the place was amazing and very clean and well put together for me and my family amd the owners stayed in contact the whole stay"
United States
Breanna C.
Stylish retreat in charming Richmond with Private Sauna and other modern touches

Carytown Home/Free Parking/Fenced Yard/Family-Friendly/4TVs

Byrd Park
8.6 out of 10, Excellent, (10)
"Nice place and convenient location"
United States
steve S.
$234 nightly
The price is $259
Nov 16 - Nov 17
Total with taxes and fees
Carytown Home/Free Parking/Fenced Yard/Family-Friendly/4TVs

The Sweet Family retreat/Fenced & Free Parking

Sauer's Gardens
9.6 out of 10, Exceptional, (54)
"Easy clean and comfortable "
United States
Mike P.
$255 nightly
The price is $283
Dec 3 - Dec 4
Total with taxes and fees
The Sweet Family retreat/Fenced & Free Parking

Richmond Oasis: Your Home Away from Home in the Heart of the City

Fairmount
8.0 out of 10, Very Good, (11)
"Not clean house, including dishes. Bad neighborhood. Did not include hot tub as listed"
United States
Adrianna S.
Richmond Oasis: Your Home Away from Home in the Heart of the City

4-bedroom waterfront homestead near Williamsburg with WiFi, AC. Book now

Lanexa
10.0 out of 10, Exceptional, (3)
"First and foremost, the property was excellent! The host, Michael was extremely welcoming and kind. The property is in top condition with new everything! The seclusion and lakefront location was to die for. Highly recommend this property as we will be back! "
United States
Kelly B.
4-bedroom waterfront homestead near Williamsburg with WiFi, AC. Book now

Cozy Bungalow convenient to U of R & shops of Libbie & Grove!

4.0 star property
Three Chopt
10.0 out of 10, Exceptional, (13)
"Property was very clean with good towels, linens, dishes. The neighborhood was very comfortable as was this property. I would not hesitate to rent this house the next time we are in Richmond."
United States
Douglas O.
Cozy Bungalow convenient to U of R & shops of Libbie & Grove!

NEW! Upscale Escape | Game Room & Spa-Like Baths

Willow Oaks
9.0 out of 10, Wonderful, (7)
"The house was great and clean on the surface. It was a cute home with a mixture of modern and old school feel. There were minor issues, however not too serious. My family was comfortable and enjoyed their stay, most especially the foosball table, air hockey, and chess/checkers games. I found opened bottles of water in the sunroom and in one of the bedrooms, a sock, and a flashlight noticeably under the nightstand. Although we didn’t stay the whole way due to weather issues (caused a power...
United States
Randy-Tawnee E.
NEW! Upscale Escape | Game Room & Spa-Like Baths

VCU • Fenced • Pet Friendly • Keyless • King Suite + 2 Queen Bedrooms

Randolph
9.8 out of 10, Exceptional, (128)
"Everything you need for a stay in Richmond, especially if you have family at VCU. "
United States
Lisa F.
VCU • Fenced • Pet Friendly • Keyless • King Suite + 2 Queen Bedrooms

The Grace Escape

Monument Avenue Park
10.0 out of 10, Exceptional, (31)
"It was a really comfortable and great place to stay as a family."
United States
Anonymous traveler
The Grace Escape

Great Location. Close to about everywhere .Can't beat the value. Check reviews!

Three Chopt
10.0 out of 10, Exceptional, (223)
"This is a great house with plenty of space for everyone. "
United States
Amanda C.
Great Location. Close to about everywhere .Can't beat the value. Check reviews!

Spacious and Cozy Oasis on Monument Avenue

Richmond
10.0 out of 10, Exceptional, (24)
"Very comfortabe and well located for a variety of activities. "
United States
David D.
Spacious and Cozy Oasis on Monument Avenue

Cozy retreat just 1 mile from the Fine Creek Brewery & eclectic wedding venue.

Powhatan
10.0 out of 10, Exceptional, (59)
"We really enjoyed our stay at your charming and cozy home. Very clean, decorated so cute, comfy bed, the towels were so soft and we loved the patio out back, so peaceful!David and Lisa were wonderful host and hostess…they took care of all our needs!Thank you and we will definitely be back!"
United States
carla e.
Cozy retreat just 1 mile from the Fine Creek Brewery & eclectic wedding venue.

Charming Cul-de-sac Retreat | Double Master + Garage + Home Office

Chesterfield
9.8 out of 10, Exceptional, (33)
"The owner was very helpful and worked with us."
United States
Carla D.
Charming Cul-de-sac Retreat | Double Master + Garage + Home Office

Spacious Carytown Home: 6BR, Free Parking!

2.0 star property
Randolph
10.0 out of 10, Exceptional, (6)
"Great location. My family enjoyed our time here. "
United States
Angela F.
$487 nightly
The price is $540
Nov 18 - Nov 19
Total with taxes and fees
Spacious Carytown Home: 6BR, Free Parking!

Pet-Friendly 3BR Near Short Pump + Big Fenced Yard

Short Pump
9.6 out of 10, Exceptional, (4)
"Stay was smooth but more utensils needed for long stay "
United States
msimms5001
Pet-Friendly 3BR Near Short Pump + Big Fenced Yard

VMFA • Carytown • Keyless • Coffee & Treats • Queen Bedrooms • Generous Deck

Museum District
10.0 out of 10, Exceptional, (126)
"Amazing location. Would stay again"
United States
kerry p.
$366 nightly
The price is $468
Nov 24 - Nov 25
Total with taxes and fees
VMFA • Carytown • Keyless • Coffee & Treats • Queen Bedrooms • Generous Deck

~THE RETREAT~

Glen Allen
9.6 out of 10, Exceptional, (24)
"If you're ever in Richmond and need a place to stay, I highly recommend this place. The pictures do not do this place justice. The grounds are really spacious, plenty of room inside and outside the home. No issues here during our stay. We loved it!"
United States
Theo L.
~THE RETREAT~

Charming 1940s Vintage Home in Hanover County

Hanover
10.0 out of 10, Exceptional, (5)
"Thanks for a great stay! We loved the property!"
United States
Jonathan V.
$571 nightly
The price is $649
Nov 16 - Nov 17
Total with taxes and fees
Charming 1940s Vintage Home in Hanover County

Charming 2-bedroom house with WiFi and AC in Richmond

Oak Grove
8.0 out of 10, Very Good, (2)
"Beware of the front concrete steps as they are all broken almost tripped several times . The backyard is overgrown with branches and outside seating was dilapidated and unkempt. Grass is minimal. House was nice inside just outside elements did not match inside."
United States
Sabrina R.
Charming 2-bedroom house with WiFi and AC in Richmond

Cozy walkable downtown retreat, 3 minutes to VCU

Downtown Richmond
9.4 out of 10, Exceptional, (15)
"We had a fabulous stay celebrating Christmas with family in Richmond. "
United States
Sue W.
$372 nightly
The price is $476
Nov 16 - Nov 17
Total with taxes and fees
Cozy walkable downtown retreat, 3 minutes to VCU
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

Find out more about Chesterfield County

Booking Tips to Find the Best Chesterfield County Vacation Homes


How much does it cost to rent a vacation home in Chesterfield County?

You can find incredible Chesterfield County vacation homes for all types of budgets: between $259 and $649 per night. The more amenities the rental has, and its proximity to popular places, the higher the price.


What is the best time to stay in a vacation home in Chesterfield County?

If you are looking for a great deal on your vacation home in Chesterfield County, consider visiting in , when prices are usually cheaper.


How many vacation homes are available for rent in Chesterfield County?

There are 327 rental houses to choose from for your trip. You’ll find holiday homes located throughout the city, near sightseeing spots, and close to local nature areas.


How do I find the best deal for a vacation home in Chesterfield County?

Begin by entering your trip dates to see what type of Chesterfield County rental houses are available. Use the map to zoom closer into the areas or zoom out to include more locations. Use the filters on the left side of your search results to narrow down by star rating, price, number of bedrooms, amenities, and more—Expedia makes it easy to score the best deal for your budget.


Why should I rent a vacation home in Chesterfield County?

Booking Chesterfield County vacation home rentals is the perfect way to spend a vacation because of the privacy, variety of amenities, and comfort you’ll have in your own space.


What amenities are available in a private vacation home?

When thinking about what you want in your Chesterfield County rental house, dream big! Depending on your budget and the area, you’ll find amenities like a private pool, hot tub, free parking, fully-equipped kitchen, in-home washer and dryer, Wi-Fi, and a beautiful view or easy access to local sightseeing spots. You can even filter your search results by accessibility to ensure that everyone in your party will be comfortable.


Why should I book a vacation home with Expedia?

Expedia has some of the best selection and deals on available vacation homes in the area—and all in one place. We reward you with members points back on every booking and ensure you get the right accommodation for the best price. And you’ll save big when you bundle your travel together, like booking a car rental in Chesterfield County along with your vacation property, into a Chesterfield County vacation package.


Can I cancel my vacation home with Expedia?

Some accommodations are free to cancel and refundable if done so by a specific date, while others may be non-refundable. To make sure that you can get your money back on cancellations, use the “free cancellation” filter during your search. Contact our customer service portal if you need help.

Chesterfield County Vacation Homes information

Number of reviews
761
Accommodation
327 Vacation Homes
Lowest Price
$259
Highest Price
$649

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