A sign for the Village of UPPERVILLE with a 'Please drive slowly' message.

Upperville cottage rentals

We found 30 cottage rentals — enter your dates for availability

Explore Upperville cottage rentals

Image of Hunt Country cottage in Upperville!

Premier Host

Hunt Country cottage in Upperville!

Sleeps 3 · 2 bedrooms · 1 bathroom

Image of Upperville Farm Cottage

Upperville Farm Cottage

Sleeps 99 · 2 bedrooms · 2 bathrooms

Image of Weekend getaway short distance from DC/Northern Virginia

Weekend getaway short distance from DC/Northern Virginia

Sleeps 4 · 1 bedroom · 1 bathroom

Image of Middleburg address - Charming Cottage with super location in country setting

Middleburg address - Charming Cottage with super location in country setting

Sleeps 2 · 1 bedroom · 1 bathroom

Image of Tranquil 2-bedroom cottage on gorgeous horse farm in The Plains

Tranquil 2-bedroom cottage on gorgeous horse farm in The Plains

Sleeps 6 · 2 bedrooms · 1 bathroom

Image of Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi

Premier Host

Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi

Sleeps 8 · 4 bedrooms · 2 bathrooms

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