Pittsylvania County family rentals

We found 729 family rentals — enter your dates for availability

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November 2025

December 2025

Find the best place to stay - Pittsylvania County

Showing deals for: 9 Feb - 12 Feb

Premier Host

Smith Mountain Lake Home with stunning views with wet cove

Sleeps 16 · 7 bedrooms · 5 bathrooms

for 3 nights, 1 home

AU$2,011 per night

includes taxes & fees

Premier Host

NEW 2024! LUXURY LAKEFRONT!Chef's Kitchen, Elevator, Firepit, Bar, Gameroom!

Sleeps 22 · 8 bedrooms · 8+ bathrooms

for 3 nights, 1 home

AU$2,950 per night

includes taxes & fees

Premier Host

Lakefront with Amazing Mountain and Lake Views, Docks, Fire Pit, Kayaks and More

Sleeps 14 · 5 bedrooms · 3+ bathrooms

for 3 nights, 1 home

AU$1,034 per night

includes taxes & fees

Cozy retreat with lots of room for outdoor activities.

Sleeps 7 · 2 bedrooms · 1 bathroom

for 3 nights, 1 cabin

AU$249 per night

includes taxes & fees

The perfect getaway for you and your people! Quiet with a gorgeous view!

Premier Host

Secluded Lakefront Cabin Resort: 5400sqft 6BR, 5ba

Sleeps 16 · 6 bedrooms · 4+ bathrooms

for 3 nights, 1 home

AU$1,243 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Pittsylvania County

Smith Mountain Lake Home with stunning views with wet cove

NEW 2024! LUXURY LAKEFRONT!Chef's Kitchen, Elevator, Firepit, Bar, Gameroom!

On The Rocks SML

Lakefront with Amazing Mountain and Lake Views, Docks, Fire Pit, Kayaks and More

Cozy retreat with lots of room for outdoor activities.

Secluded Lakefront Cabin Resort: 5400sqft 6BR, 5ba

Find spaces that suit your style

Family-friendly Rentals in Pittsylvania County

Holiday Rental options in Pittsylvania County