Chesterfield County Vacation Rentals

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Chesterfield County Vacation Rentals

Charming 1-bedroom suite with WiFi and AC in Bon Air

Charming 1-bedroom suite with WiFi and AC in Bon Air

Bon Air VA
$254 nightly
The price is $292 total per night
$292 total
Jan 13 - Jan 14, 2026
Total with taxes and fees
Guests staying at this vacation home enjoy features like a water park, a gym, and barbecue grills.
Free WiFi
Air conditioning
PRIVATE 2 BEDROOM w/ BATH/SHOWER COMBO - Chesterfield, VA

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

2 out of 5
Chesterfield VA
$68 nightly
The price is $78 total per night
$78 total
Dec 21 - Dec 22
Total with taxes and fees
This vacation home features a gym and laundry facilities.
Washer
Dryer
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 VA
$186 nightly
The price is $213 total per night
$213 total
Dec 21 - Dec 22
Total with taxes and fees
At this houseboat, guests have access to features like laundry facilities. Friendly staff can provide luggage storage, and also offer advice about sightseeing. This houseboat also has a garden.
Kitchen
Washer
MV GiaMaria

MV GiaMaria

3.5 out of 5
9954 Hoke Brady Road Richmond VA
$155 nightly
The price is $177 total per night
$177 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
Guests staying at this houseboat enjoy features like a marina and free WiFi in public areas. Free parking is available if you drive.
Kitchen
Washer
Cookie B

Cookie B

3 out of 5
9954 Hoke Brady Road Richmond VA
$164 nightly
The price is $187 total per night
$187 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
Guests staying at this houseboat enjoy a marina, free WiFi in public areas, and a library. If you drive, put free parking to good use. Additional amenities include laundry facilities, a hair salon, and a convenience store.
Kitchen
Dryer
Lovely 2 Bedroom in the Heart of The Fan

Lovely 2 Bedroom in the Heart of The Fan

Richmond VA
$271 nightly
The price is $289 total per night
$289 total
Jan 7 - Jan 8, 2026
Total with taxes and fees
At this apartment, guests have access to features like laundry facilities.
Kitchen
Washer
Spacious Carytown Home: 6BR, Free Parking!

Spacious Carytown Home: 6BR, Free Parking!

2 out of 5
Richmond VA
$487 nightly
The price is $533 total per night
$533 total
Jan 7 - Jan 8, 2026
Total with taxes and fees
At this vacation home, guests have access to features like laundry facilities.
Kitchen
Washer
The Sweet Family retreat/Fenced & Free Parking

The Sweet Family retreat/Fenced & Free Parking

Richmond VA
$266 nightly
The price is $292 total per night
$292 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
Guests staying at this vacation home have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Nest & Rest/Free Parking/Museum/City Access

Nest & Rest/Free Parking/Museum/City Access

Richmond VA
$133 nightly
The price is $148 total per night
$148 total
Jan 7 - Jan 8, 2026
Total with taxes and fees
At this apartment, guests have access to a gym, laundry facilities, and a garden. You can put free offsite parking to good use if you drive.
Kitchen
Washer
Luxury Apt in Diamond District - Scott’s Addition

Luxury Apt in Diamond District - Scott’s Addition

Richmond VA
At this apartment, guests have access to a gym and barbecue grills.
Pool
Washer
Spacious 5BD 5.5BA house in the Heart of Richmond

Spacious 5BD 5.5BA house in the Heart of Richmond

2 out of 5
Richmond VA
At this vacation home, guests have access to features like laundry facilities.
Kitchen
Washer
Landing Apartments near Virginia Union University

Landing Apartments near Virginia Union University

3.5 out of 5
2005 Brook Road Richmond VA
Guests of Landing Apartments near Virginia Union University enjoy features like free WiFi in public areas. If you drive, take advantage of free parking.
Kitchen
Washer
Downtown Living in Richmond's Amazing Shockoe Bottom

Downtown Living in Richmond's Amazing Shockoe Bottom

Richmond VA
$211 nightly
The price is $226 total per night
$226 total
Dec 30 - Dec 31
Total with taxes and fees
At this apartment, guests have access to features like laundry facilities.
Kitchen
Washer
The Studio@ Eanes Drug

The Studio@ Eanes Drug

Richmond VA
$135 nightly
The price is $154 total per night
$154 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
At this apartment, guests have access to features like laundry facilities.
Kitchen
Washer
Historic Haven in Church Hill

Historic Haven in Church Hill

Richmond VA
$145 nightly
The price is $166 total per night
$166 total
Dec 21 - Dec 22
Total with taxes and fees
At this apartment, guests have access to features like laundry facilities.
Kitchen
Washer
Vibrant 1-Bedroom Loft with Free Parking and Wifi

Vibrant 1-Bedroom Loft with Free Parking and Wifi

Richmond VA
This apartment features a gym and laundry facilities.
Kitchen
Washer
Pool house

Pool house

Richmond VA
$508 nightly
The price is $581 total per night
$581 total
Dec 21 - Dec 22
Total with taxes and fees
An outdoor pool and a hot tub are features at this vacation home.
Pool
Hot Tub
Cozy 4 bed 2 bath house located less than 4 minutes from the Richmond Airport.

Cozy 4 bed 2 bath house located less than 4 minutes from the Richmond Airport.

Henrico VA
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has a garden.
Kitchen
Washer
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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.

Hotel Options in Chesterfield County

    La Quinta Inn & Suites by Wyndham Richmond-Midlothian

    La Quinta Inn & Suites by Wyndham Richmond-Midlothian

    1301 Huguenot Road Midlothian VA
    $104 nightly
    The price is $121 total per night from Jan 4 to Jan 5
    $121 total
    Jan 4 - Jan 5, 2026
    Total with taxes and fees
    8.2/10 Very Good! (1,508 reviews)
    Country Inn & Suites by Radisson, Richmond I-95 South, VA

    Country Inn & Suites by Radisson, Richmond I-95 South, VA

    2401 Willis Rd Richmond VA
    $83 nightly
    The price is $97 total per night from Jan 11 to Jan 12
    $97 total
    Jan 11 - Jan 12, 2026
    Total with taxes and fees
    8.2/10 Very Good! (1,451 reviews)
    DoubleTree by Hilton Richmond - Midlothian

    DoubleTree by Hilton Richmond - Midlothian

    1021 Koger Center Blvd Richmond VA
    $149 nightly
    The price is $173 total per night from Dec 21 to Dec 22
    $173 total
    Dec 21 - Dec 22
    Total with taxes and fees
    8/10 Very Good! (1,000 reviews)

Orbitz makes it easy to find vacation rentals in Chesterfield County 

🏠 What is the best price for a Chesterfield County vacation rental?


Chesterfield County rentals range between $78 and $581 per night. At Orbitz, we have a vacation rental for every budget.


🏠 What types of vacation rentals in Chesterfield County can I rent?


Choose from apartments to beautifully decorated vacation homes, condo resorts or even B&Bs or motels for your next Chesterfield County getaway. Orbitz filters your search results so you can find the best Chesterfield County vacation rental for you. We have tons of options.


🏠 Are cancellations free on Chesterfield County vacation rentals with Orbitz?


You may be able to cancel or amend your Chesterfield County vacation rental booking free of charge before a pre-agreed deadline. Make sure to check the terms of cancellation before you book—so you know exactly where you stand. 


🏠 How do I find the best vacation rental deals in Chesterfield County?


Enter your travel dates, and we’ll do the rest. You can then browse our exciting deals and all the tempting vacation rentals we have on offer in Chesterfield County by filtering your search by amenities, prices, and property types and look at customers ratings to help you pick.


🏠 How do I cancel my vacation rental booking through Orbitz


Vacation rentals have slightly different rules to other bookings on Orbitz. Usually, you need to contact your property manager, you may be able to get a full refund before the cancellation date. Click My TripsOpens in a new window on your Orbitz account page to find the right information contact. If you need more help, visit our Customer ServiceOpens in a new window page. 


🏠 What are the advantages of booking a vacation rental in Chesterfield County?


When you book a Chesterfield County vacation rental, you have the privacy of home and can add on those luxury amenities of a hotel. Filter your vacation rental results to find a place with a hot tub or pool, games rooms or large patio with a barbecue. With so much choice on offer, it’s easy to plan the perfect trip with Orbitz. 


🏠 Where can I find vacation rentals in Chesterfield County?


Escape back to nature and check out some of the smaller towns. You’ll find great vacation rentals right across Chesterfield County—with plenty of hidden gems. We also have plenty of inventory in Chesterfield County main cities and near popular attraction spots.


🏠 Why should I book my Chesterfield County vacation rental with Orbitz?


At Orbitz, we search the market for the best accommodation, flights, and car rental deals, so you don’t have to. We’ll help you build your dream Chesterfield County vacation. With plenty of vacation rentals on offer, you can be sure to find the one that’s right for you in just a few clicks. 


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