Photo by Nick Pagano

Chesterfield Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

Tonight
Nov 13 - Nov 14
Tomorrow
Nov 14 - Nov 15
This weekend
Nov 14 - Nov 16
Next weekend
Nov 21 - Nov 23

Vacation Rentals in Chesterfield

Interior
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, (4)
"We only stayed as a brief overnight stay. The little apt was perfect for what we needed. The horse farm property is absolutely gorgeous and I wish I could have looked around more."
United States
Debbie M.
$245 nightly
The price is $294
Nov 22 - Nov 23
Total with taxes and fees
Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.
1 bedroom, free WiFi, bed sheets
Cozy Custom Offgrid RV in brilliant Chesterfield with AC, Heat and WiFi

Cozy Custom Offgrid RV in brilliant Chesterfield with AC, Heat and WiFi

2.0 star property
Chesterfield
$138 nightly
The price is $166
Nov 14 - Nov 15
Total with taxes and fees
Cozy Custom Offgrid RV in brilliant Chesterfield with AC, Heat and WiFi
Dining
PRIVATE 2 BEDROOM w/ BATH/SHOWER COMBO - Chesterfield, VA

PRIVATE 2 BEDROOM w/ BATH/SHOWER COMBO - Chesterfield, VA

2.0 star property
Hampton Park
$78 nightly
The price is $94
Nov 23 - Nov 24
Total with taxes and fees
PRIVATE 2 BEDROOM w/ BATH/SHOWER COMBO - Chesterfield, VA
Dock
Cookie B

Cookie B

3.0 star property
Richmond
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
$174 nightly
The price is $198
Nov 19 - Nov 20
Total with taxes and fees
Cookie B
View from property
MV GiaMaria

MV GiaMaria

3.5 star property
Richmond
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
$189 nightly
The price is $215
Nov 16 - Nov 17
Total with taxes and fees
MV GiaMaria
Property grounds
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, (112)
"Thank you for an amazing and peaceful experience "
United States
Jam 4.
$186 nightly
The price is $223
Nov 16 - Nov 17
Total with taxes and fees
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
Microwave, oven, stovetop, dishwasher
Tourist Home of Richmond 1-bedroom Apartment - Church Hill North TH08

Tourist Home of Richmond 1-bedroom Apartment - Church Hill North TH08

Woodville
10.0 out of 10, Exceptional, (1)
"Nice place with a comfy home feel very clean great spot despite the area not being the best being in the home made you not notice definitely five star location "
United States
Alex G.
$201 nightly
The price is $257
Nov 18 - Nov 19
Total with taxes and fees
Tourist Home of Richmond 1-bedroom Apartment - Church Hill North TH08
1 bedroom, WiFi
Charming 1-bedroom apartment in Mechanicsville

Charming 1-bedroom apartment in Mechanicsville

Mechanicsville
10.0 out of 10, Exceptional, (3)
"Had a great stay while fishing the james river. "
United States
Travis D.
$129 nightly
The price is $155
Nov 16 - Nov 17
Total with taxes and fees
Charming 1-bedroom apartment in Mechanicsville
Smart TV
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, (4)
"This house met all of our needs while we were in town for a sports event. Lots is space, small back yard, everything needed in the kitchen. "
United States
Kari R.
$277 nightly
The price is $355
Dec 3 - Dec 4
Total with taxes and fees
Charming 3-bedroom townhome with WiFi in delightful Richmond
Terrace/patio
Charming 3-bedroom house with all inclusive and AC in Richmond

Charming 3-bedroom house with all inclusive and AC in Richmond

Richmond
8.0 out of 10, Very Good, (1)
"Our host was very good at communicating with us. The house was recently remodeled and tastefully done. "
United States
Theda G.
$237 nightly
The price is $284
Nov 16 - Nov 17
Total with taxes and fees
Charming 3-bedroom house with all inclusive and AC in Richmond
Private kitchen
Modern 5 Bedroom City Retreat + Walkable + Private Baths + Large Groups

Modern 5 Bedroom City Retreat + Walkable + Private Baths + Large Groups

2.0 star property
Carver
10.0 out of 10, Exceptional, (1)
"Our large family group enjoyed our stay here. The house is well-appointed and large. Everyone loved having their own bathrooms. Everything was clean and new condition. Just some minor things that were not deal-breakers for us. When I polled my family we pretty much all wished we had brought our own pillows. Parking is tight and awkward when neighbors are also parked, but at least there are reserved spots in a busy neighborhood. There are noise machines for each bed which is nice, but perhaps...
United States
Meg T.
$453 nightly
The price is $580
Nov 18 - Nov 19
Total with taxes and fees
Modern 5 Bedroom City Retreat + Walkable + Private Baths + Large Groups
Exterior detail
Cozy studio in FAN/museums /free parking

Cozy studio in FAN/museums /free parking

Fan District
9.6 out of 10, Exceptional, (27)
"Loved the apartment and the street of the house was so pretty. Great stay"
United States
Keylee R.
$115 nightly
The price is $130
Nov 24 - Nov 25
Total with taxes and fees
Cozy studio in FAN/museums /free parking
Exterior
Magnolias, a chill out place.

Magnolias, a chill out place.

Richmond
9.4 out of 10, Exceptional, (19)
"Enjoyed my stay a lot! The property definitely has charm, the experience was very laid back. "
United States
Grace
$102 nightly
The price is $123
Dec 1 - Dec 2
Total with taxes and fees
Magnolias, a chill out place.
Microwave, oven, dishwasher
2 Rooms -2 Queen Beds Apartment in pleasant Richmond with AC, WiFi

2 Rooms -2 Queen Beds Apartment in pleasant Richmond with AC, WiFi

Fan District
10.0 out of 10, Exceptional, (6)
"The owner was very prompt and clear in communication, lives in the same building, so greeted us warmly, the property was clean and cozy and well appointed. The neighborhood is close to so many sites we wanted to see. Parking can be a little challenging in that area, but nothing we weren't able to work around."
United States
Janel G.
$277 nightly
The price is $355
Nov 16 - Nov 17
Total with taxes and fees
2 Rooms -2 Queen Beds Apartment in pleasant Richmond with AC, WiFi
Property grounds
Sunny, Spacious Suite Green & Shaded Backyard

Sunny, Spacious Suite Green & Shaded Backyard

Northern Barton Heights
10.0 out of 10, Exceptional, (2)
"The apartment was perfect. Awesome location! Easy to get downtown and surrounding areas. The host was very responsive and diligent. Community pool was one block away, with 20 tennis courts and playground. Had a wonderful time visiting my family. Thank you. "
United States
Robin C.
$213 nightly
The price is $273
Nov 19 - Nov 20
Total with taxes and fees
Sunny, Spacious Suite Green & Shaded Backyard
Fridge, microwave, oven, stovetop
Oaks Retreat Carytown House: Family & Pet Friendly

Oaks Retreat Carytown House: Family & Pet Friendly

Randolph
9.6 out of 10, Exceptional, (10)
"Very very nice place but in a little sketchy part of town. Only 1 parking spot and someone took it so we had to street park. Pipes knocked alot through the night. "
United States
Crystal W.
$233 nightly
The price is $258
Nov 19 - Nov 20
Total with taxes and fees
Oaks Retreat Carytown House: Family & Pet Friendly
Interior
Close to Fort Gregg-Adams, VSU & Southside Medical – Comfort & Convenience

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

2.0 star property
Petersburg
9.4 out of 10, Exceptional, (3)
"The property was exactly as listed. Very responsive communication from the owner."
United States
Andrew W.
$297 nightly
The price is $357
Nov 26 - Nov 27
Total with taxes and fees
Close to Fort Gregg-Adams, VSU & Southside Medical – Comfort & Convenience
Outdoor dining
Colorful private guesthouse in charming Richmond with Parking

Colorful private guesthouse in charming Richmond with Parking

Northern Barton Heights
10.0 out of 10, Exceptional, (4)
"Such a fun place to stay! Room is nicely decorated. Easy check in/check out. Never stayed in this part of RVA before. We will definitely stay here again!"
United States
Teresa M.
$180 nightly
The price is $230
Nov 17 - Nov 18
Total with taxes and fees
Colorful private guesthouse in charming Richmond with Parking
Exterior
Steel Magnolias Cozy Main Home in Amelia County

Steel Magnolias Cozy Main Home in Amelia County

Amelia Court House
9.8 out of 10, Exceptional, (10)
"Wonderful house in the country, perfect place to unwind and watch the sun go down. Jenny is a pleasure to deal with and made sure everything was perfect for my stay."
United States
David H.
$277 nightly
The price is $292
Nov 30 - Dec 1
Total with taxes and fees
Steel Magnolias Cozy Main Home in Amelia County
Fridge, microwave, oven, stovetop
Recline at Timberline! Family friendly!

Recline at Timberline! Family friendly!

South chesterfield
9.2 out of 10, Wonderful, (47)
"Enjoyed our stay."
United States
Lorene B.
Recline at Timberline! Family friendly!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesterfield Hotel Reviews

Hyatt Place Richmond Airport

Hyatt Place Richmond Airport

10/10 Excellent
"The room was really clean and cozy. The breakfast was good, however I didn't like you had to pay for parking and it was in a shopping center so what is so exclusive about the parking lot that you are sharing it with a restaurant in front of the hotel. "
Ranell 1-night trip
Posted 1 day ago
Hyatt Place Richmond Airport

Find out more about Chesterfield

Everything you need to know about Chesterfield 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 vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chesterfield vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterfield. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chesterfield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $94 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chesterfield rentals

At Expedia, we put the best Chesterfield 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 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 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. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Chesterfield?

Yes, we give you a choice of vacation rentals close to popular local attractions in Chesterfield, or you can choose a more secluded option if you're looking for relaxation. Chesterfield is known for its shopping and golf courses. Make sure you have time to check out the parks and museums during your trip.

What are some of the best vacation rentals that Chesterfield has to offer?

Stylish retreat in charming Richmond with Private Sauna and other modern touches: This vacation home rental outside of Chesterfield offers a fireplace, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Chesterfield?

Expedia has 7 vacation rentals for your stay in Chesterfield.

What can I see and do in Chesterfield?

While exploring the area, visit family-friendly sights like Iron Bridge Sports Park, or get outside and enjoy nature at Appomattox River. Pocahontas State Park and Castlewood are other places to visit while you're in town.

What are vacation rentals like in Chesterfield?

Vacation rentals are privately owned properties you can stay in for a short or long stay in Chesterfield. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for a small group gathering.