Middleburg Vacation Rentals

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Vacation Rentals in Middleburg

Luxury NEW! Woodhaven Reserve! Private Pool + Hot Tub

Purcellville VA

With a stay at this vacation home in Purcellville, you'll be within a 10-minute drive of Dragon Hops and Historic Downtown Purcellville.

Pool

Hot Tub

Leesburg Hideaway- King Bed + Private Backyard

Leesburg VA

With a stay at this vacation home in Leesburg, you'll be within a 15-minute drive of One Loudoun and Tally Ho Theatre.

Kitchen

Washer

Newly Renovated Adorable Private Basement with Bathroom

Herndon VA

Located in Herndon (Franklin Farm), this vacation home is within a 10-minute drive of Steven F. Udvar-Hazy Center and Fair Oaks Mall.

Washer

Dryer

Indulge in Elegance: 7 BR Manor in Historic Waterford

Waterford VA

Located in Waterford, this vacation home is in a rural location, a 2-minute drive from Village Winery and 9 minutes from Hunters Run Wine Tasting Barn.

Pool

Kitchen

Modern Country House on the Shenandoah River

Charles Town WV

When you stay at this vacation home in Charles Town, you'll be on the waterfront and steps from Shenandoah River.

Kitchen

Washer

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

Cottage on King | Charming Historic Leesburg Home

Leesburg VA

$434 nightly

$499 total

Jul 1 - Jul 2

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 Tally Ho Theatre.

Kitchen

Washer

Quiet Highland Home set on gorgeous rolling hills and farm in Western Loudoun

Purcellville VA

Located in Purcellville, this vacation home is within a 5-minute drive of Fireman's Field and Loudoun Valley Community Center.

Washer

Dryer

🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries

Linden VA

Located in Linden, this vacation home is in the mountains, within a 10-minute drive of Fox Meadow Winery and Tuckers Lane Trailhead.

Hot Tub

Kitchen

4BR RiverVIEWS, Comm Pool & River Access, Barrel Sauna, Massage Chairs, Game Rm

Harpers Ferry WV

With a stay at this vacation home in Harpers Ferry, you'll be within a 15-minute drive of Harpers Ferry National Historical Park and Virginius Island.

Kitchen

Washer

Terra Alta - Incredible River Views and Hot Tub!

Charles Town WV

$416 nightly

$463 total

Jul 1 - Jul 2

Total with taxes and fees

With a stay at this vacation home in Charles Town, you'll be on a river, within a 15-minute drive of Hollywood Casino at Charles Town Races and Shenandoah River.

Hot Tub

Kitchen

Private Trail To Wine! 5-bedroom Farmhouse In Heart Of Virginia Horse Country

Delaplane VA

Located in Delaplane, this vacation home is in a rural location, within a 5-minute drive of RdV Vineyards and Delaplane Cellars.

Hot Tub

Kitchen

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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.