Middleburg Vacation Rentals

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Vacation Rentals in Middleburg

Harpers Ferry: Fireplace • Patio • Near River Tubing & Downtown Harpers Ferry

Harpers Ferry WV

Located in Harpers Ferry, this vacation home is within a 15-minute drive of Harpers Ferry National Historical Park and Hollywood Casino at Charles Town Races.

Kitchen

Washer

Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV

Harpers Ferry WV

$394 nightly

$428 total

Aug 10 - Aug 11

Total with taxes and fees

When you stay at this vacation home in Harpers Ferry, you'll be in the mountains, within a 15-minute drive of Harpers Ferry National Historical Park and Hollywood Casino at Charles Town Races.

Hot Tub

Kitchen

A unique mountaintop getaway overlooking Willow Croft Winery.

Leesburg VA

Located in Leesburg, this vacation home is on a river, within a 10-minute drive of Stone Tower Winery and Catoctin Valley.

Kitchen

Free WiFi

Storybook cottage on Leesburg's most historic block — walk to everything

Leesburg VA

$469 nightly

$539 total

Aug 18 - Aug 19

Total with taxes and fees

With a stay at this vacation home, you'll be centrally located in Leesburg, within a 15-minute drive of One Loudoun and Catoctin Valley.

Beautiful 3 BR 2 Bath Private Main-first floor with AC Heat in Leesburg, VA

Leesburg VA

Located in Leesburg, this vacation home is within a 5-minute drive of Catoctin Valley and Fleetwood Farm Winery.

Kitchen

Washer

Gorgeous, Wooded 3 Acre Estate -5 Bed/4 Bath-Leesburg/Brambleton/Aldie area

Leesburg VA

Located in Leesburg, this vacation home is in a rural location, a 3-minute drive from Catoctin Valley and 5 minutes from Fleetwood Farm Winery.

Kitchen

Washer

Retreat in Historic Downtown Leesburg - Walkable to Everything!

Leesburg VA

$412 nightly

$474 total

Aug 10 - Aug 11

Total with taxes and fees

With a stay at this vacation home in Leesburg (Leesburg's Old and Historic District), you'll be steps from Catoctin Valley and Dodona Manor.

Ashburn 4-BR Homestay / Close to Dulles & METRO

Brambleton VA

With a stay at this vacation home in Ashburn, you'll be within a 15-minute drive of Reston Town Center and Brambleton Regional Park Golf Course.

Kitchen

Washer

Main Street USA -- Walk to Everything

Purcellville VA

$651 nightly

$729 total

Aug 19 - Aug 20

Total with taxes and fees

With a stay at this vacation home in Purcellville, you'll be within a 5-minute walk of Washington & Old Dominion Trail Regional Park and Historic Downtown Purcellville.

Kitchen

Air conditioning

YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor

Middleburg VA

Located in Middleburg, this vacation home is in a rural location, a 5-minute drive from Greenhill Winery & Vineyards and 5 minutes from Red Fox Fine Art.

Quiet Virginia Wine Country Retreat

Delaplane VA

Located in Delaplane, this vacation home is in a rural location, within a 10-minute drive of Delaplane Cellars and Aspen Dale Winery at the Barn.

Kitchen

Washer

HOT TUB! PRIME LEAF PEEPING! Gorgeous 4BR

Front Royal VA

When you stay at this vacation home in Front Royal, you'll be on a river, within a 5-minute drive of Shenandoah River and John T Shipe JR Park.

Hot Tub

Kitchen

Don't see what you're looking for?

See all available properties in Middleburg

View all properties

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.