Find Vacation Rentals in Chesterfield County

We have 458 properties to choose from
Chesterfield County
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Chesterfield County
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Popular Chesterfield County Vacation Rentals

Find the perfect Chesterfield County vacation rental

House Moseley
$931 per night
House ∙ 20 guests ∙ 8 bedrooms
Moseley, Matoaca, Chesterfield County
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Vrbo
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House Chesterfield
$681 per night
House ∙ 12 guests ∙ 6 bedrooms
5.0
Outstanding (1 rating)
Chesterfield, Dale, Chesterfield County
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Vrbo
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House Woodlake
$451 per night
House ∙ 12 guests ∙ 6 bedrooms
4.9
Outstanding (34 ratings)
Woodlake, Matoaca, Chesterfield County
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Vrbo
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House Moseley
$309 per night
House ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding (22 ratings)
Moseley, Matoaca, Chesterfield County
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Vrbo
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House Woodlake
$452 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding (11 ratings)
Woodlake, Matoaca, Chesterfield County
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Vrbo
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House Moseley
$1,155 per night
House ∙ 18 guests ∙ 8 bedrooms
5.0
Outstanding (5 ratings)
Moseley, Matoaca, Chesterfield County
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Vrbo
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House Chesterfield
$382 per night
House ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding (36 ratings)
Chesterfield, Dale, Chesterfield County
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Vrbo
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House Chesterfield
$251 per night
House ∙ 10 guests ∙ 3 bedrooms
5.0
Outstanding (6 ratings)
Chesterfield, Dale, Chesterfield County
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Vrbo
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House South Chesterfield
$175 per night
House ∙ 6 guests ∙ 3 bedrooms
4.7
Excellent (39 ratings)
South Chesterfield, Bermuda, Chesterfield County
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Vacation rentals and apartments with air conditioning

Apartment  Chesterfield County
$114 per night
Apartment ∙ 2 guests ∙ 1 bedroom
5.0
Outstanding (2 ratings)
Chesterfield County, Virginia, United States
Air conditioning
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Vrbo
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House  Moseley
$649 per night
House ∙ 12 guests ∙ 6 bedrooms
4.5
Excellent (16 ratings)
Moseley, Matoaca, Chesterfield County
Air conditioning
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Vrbo
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House  Chesterfield County
$216 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding (28 ratings)
Chesterfield County, Virginia, United States
Air conditioning
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Vacation rentals with Wi-Fi

House  Chesterfield
$113 per night
House ∙ 3 guests ∙ 2 bedrooms
Chesterfield, Dale, Chesterfield County
Internet
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Vrbo
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House  Chesterfield
$184 per night
House ∙ 8 guests ∙ 3 bedrooms
Chesterfield, Dale, Chesterfield County
Internet
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Vrbo
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Apartment  Chesterfield County
$125 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
Chesterfield County, Virginia, United States
Internet
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Vrbo
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Best vacation rentals with a balcony

Condo  Bon Air
$178 per night
Condo ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding (2 ratings)
Bon Air, Midlothian, Chesterfield County
Balcony
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Vrbo
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House  Moseley
$2,532 per night
House ∙ 16 guests ∙ 19 bedrooms
5.0
Outstanding (2 ratings)
Moseley, Matoaca, Chesterfield County
Balcony
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Vrbo
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Bed and breakfast  Chesterfield
$94 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
Chesterfield, Dale, Chesterfield County
Balcony
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Agoda
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Frequently Asked Questions

Can I find cheap vacation rentals in Chesterfield County?

Accommodation in Chesterfield County cost from $60 per night.

Is there a wide selection of vacation rentals in Chesterfield County?

Our large collection of vacation homes makes it easy to filter and compare 458 offers in Chesterfield County.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Vacation Rentals in Chesterfield

Save hundreds with a vacation home rental from Tripping.com and forget the hotel room. For the ultimate getaway, Chesterfield offers 50 affordable vacation rentals with a price to match your budget and accommodation needs. Prices in Chesterfield start at an average price of $58 a night with long-term rentals averaging $25 a month. These vacation rentals offer a range of amenities, so you’ll feel right at home. For those looking to stay in a corporate rental, 40 of Chesterfield’s rentals offer high speed WiFi Internet so you can easily keep in touch with your company or team. Go for a swim at one of the 8 properties complete with pool or jacuzzi, or relax with a night of cable TV in any of our 24 vacation home rentals. Traveling with your dog or cat? Choose from 24 pet-friendly rentals in Chesterfield that allow you to bring your extended family along.Tripping.com’s home rentals offer far more room and comfort than a hotel, providing a safe and spacious place for you and your pets. Many properties allow you to book directly online, so once you find that perfect vacation rental, you’ll be all set to go! Search properties from 5 vacation rental sites in Chesterfield where the top providers in that area are HRS Holidays, Expedia, and Booking.com. There are 16 HRS Holidays rentals, 12 Expedia short term rentals and 10 Booking.com vacation rentals.

Where are travelers searching to stay Chesterfield District?

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