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Chesterfield County family rentals

We found 626 family rentals — enter your dates for availability

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November 2025

December 2025

Find the best place to stay - Chesterfield County

Showing deals for: 18 Feb - 21 Feb

Premier Host

4-bedroom house in charming Midlothian 20 min to Richmond and Petersburg.

Sleeps 10 · 4 bedrooms · 2+ bathrooms

for 3 nights, 1 home

NZ$741 per night

includes taxes & fees

Premier Host

Luxe Cottage - South Chesterfield Stylishly renovated, w/ large master suite

Sleeps 8 · 3 bedrooms · 2 bathrooms

for 3 nights, 1 home

NZ$682 per night

includes taxes & fees

Premier Host

Midlothian 3 Bedroom getaway for up to 8 guests!

Sleeps 8 · 3 bedrooms · 3 bathrooms

for 3 nights, 1 apartment

NZ$707 per night

includes taxes & fees

King Bedroom Retreat – Your serene escape awaits with a comfy king bed, sliding door access, and an abundance of natural light. Need privacy? Just draw the curtains and unwind in total comfort!

Premier Host

Globetrotter's Suite in Historic Richmond w/ Patio

Sleeps 4 · 2 bedrooms · 1 bathroom

for 3 nights, 1 apartment

NZ$376 per night

includes taxes & fees

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

Sleeps 6 · 3 bedrooms · 1 bathroom

for 3 nights, 1 home

NZ$472 per night

includes taxes & fees

Find spaces that suit your style

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Condo/Apartment

Find the best place to stay - Chesterfield County

4-bedroom house in charming Midlothian 20 min to Richmond and Petersburg.

Lakefront Guest Suite Near Richmond

Luxe Cottage - South Chesterfield Stylishly renovated, w/ large master suite

Midlothian 3 Bedroom getaway for up to 8 guests!

Globetrotter's Suite in Historic Richmond w/ Patio

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

Find spaces that suit your style

Family-friendly Rentals in Chesterfield County

Holiday Rental options in Chesterfield County