Chesterfield vacation rentals

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Best Chesterfield vacation rentals

Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm. - Chesterfield - Outdoors view
Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.
Chesterfield, VA
10Wonderful(4)
Apartment
$279+
Check availability
Charming Cul-de-sac Retreat | Double Master + Garage + Home Office - Chesterfield - Building
Charming Cul-de-sac Retreat | Double Master + Garage + Home Office
Chesterfield, VA
9.5Wonderful(28)
House
Free Wi-Fi
$533+
Check availability
1-Bedroom w/ private entrance, Patio, & Parking - Chesterfield - Living room
1-Bedroom w/ private entrance, Patio, & Parking
Chesterfield, VA
10Wonderful(1)
House
$139+
Check availability
Walk Central. Museum district. Scott's Addition. 2BR - King and full bed. - Chesterfield - Bedroom
Walk Central. Museum district. Scott's Addition. 2BR - King and full bed.
Chesterfield, VA
9.5Wonderful(22)
Condo
Free Wi-Fi
$127+
Check availability
Serene home with all the comforts of a fully designed space- 3 /2 House - Chesterfield - Kitchen
Serene home with all the comforts of a fully designed space- 3 /2 House
Chesterfield, VA
10Wonderful(1)
House
$178+
Check availability
Charming Retreat with Pool Table in Chesterfield! - Chesterfield - Kitchen
Charming Retreat with Pool Table in Chesterfield!
Chesterfield, VA
10Wonderful(2)
House
Parking
Free Wi-Fi
$296+
Check availability
Virginia poolside Oasis: your Woodland Escape - Chesterfield - Building
Virginia poolside Oasis: your Woodland Escape
Chesterfield, VA
House
$261+
Check availability
Charming 4-bedroom house with WiFi, AC in pleasant Chesterfield - Chesterfield - Living room
Charming 4-bedroom house with WiFi, AC in pleasant Chesterfield
Chesterfield, VA
10Wonderful(2)
House
$284+
Check availability
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

May
July
$212
$143
Cheapest month to stay with an average 57% drop in price.
Most expensive month to stay with an average 88% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Chesterfield vacation rental deals

  • The best vacation rental properties in Chesterfield are Charming Cul-de-sac Retreat | Double Master + Garage + Home Office (9.5, 28 reviews), Walk Central. Museum district. Scott's Addition. 2BR - King and full bed. (9.5, 22) and Walk Central. Museum district. Scott's Addition. 2BR - King and full bed. (9.5, 22), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Chesterfield, you should consider visiting during the low season. The cheapest vacation homes in Chesterfield can be found in May and October.
  • The cheapest night for renting a vacation home in Chesterfield is Sunday. In contrast, the most expensive is Thursday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Chesterfield for 33 days.

FAQs when booking a vacation home in Chesterfield

  • How much is a vacation rental for a week in Chesterfield?

    The average price for a weekly Chesterfield vacation rental found by KAYAK users in the last 2 weeks is $268.

  • How much is a vacation rental for a month in Chesterfield?

    The average price for a monthly Chesterfield vacation rental found by KAYAK users in the last 2 weeks is $1,150.

  • What types of vacation rentals are available in Chesterfield?

    There are loads of different property types that you can make your vacation home in Chesterfield. You’ll find apartments, caravans, condos and houses.

  • How can I find vacation rentals near me in Chesterfield?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Chesterfield?

Our map will help you find the perfect place to stay in Chesterfield by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Chesterfield